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Dane, it's your brother.

What's going on, Dane?

I just heard Courtney and Nicole telling you that

the FBI is involved with something.

Dane, what happened? What have you done?

Oh, my god! I'm so scared right now.

What, what have you done?

What is going on? Why are you doing this to me?

Why aren't you answering your call?

Oh, my gosh. Please call me.

Please call me!

His mother.

His wife.

His son.

His brother.

Love.

Betrayal.

Revenge.

Never in a million years

could I believe he would bury me alive.

What I'm not asking you to talk about,

but I'm talking about- - I understand.

Everybody wants to talk about it. It's fascinating.

I'm not trying to relive trauma, but like how do you dis-

Like, is there a phone call?

The brother was Cook's business manager.

Prior to that, McCauley worked as a corrections officer.

A person that spent so much time

pretending to be something he wasn't.

You're in this fantasy.

From the early gigs in front of nine people

to the greatest space for standup comedy,

all the while feeling like something's not right.

And it ended with three words:

To the future.

To the future.

From the moment he left that bank, my brother disappeared.

Like Bonnie and Clyde. Gone!

This was just the beginning.

Why, Darryl?

Why all this?

What a fucking waste!

Ready?

Okay!

If I can offer any advice

or if there's anything that people get

from this conversation,

it's sign your own checks.

Roll credits.

My name is Dane Cook.

I was born in Massachusetts, March 18th, 1972.

We done?

Okay! I'm ready to start again, and now I'm ready for lunch.

The part of Arlington that I grew up in,

I used to think that we were lower middle class

and I found out years later

we were upper poor.

My mom and dad did a pretty good job doing anything

and everything to kind of keep us in the end of town,

which was called "The Heights."

It was great! It was like a little dirty little town.

Wasn't a lot going on, but we didn't know that.

There was a pharmacy, a sub shop, a pizza parlor.

As we see,

Al's making a pizza right in the door right now

and he's such a happy pizza boy.

I didn't realize until I left how Boston Redneck I was.

And it was just, "Get the fuck out of the house!"

Go until the streetlights came on.

Me and Heraldo. Now it can be told.

This 101 Wright Street is where I grew up.

In the neighborhood, we had the McKennas,

we had the McGonigles, then we had the McNamaras,

then we had the Maloneys and the Mulaneys.

And then McCauley and then Cook.

This is confusing and I feel like this is where I need,

like, chyrons or things

popping up on the screen.

Let's start here.

Courtney is my little sister.

There was Darryl and Kelly,

and that was from my mom's previous marriage to Jim.

They were all funny.

They were funny in a different way than my family was funny.

His family was more clever

and they'd present the joke more.

Water?

I'll just use my shirt in case I get emotional.

It broke us out of that tension.

Comedy triggers everything back to some normalcy.

He would perform for us in the living room.

He had my parents cracking up at 12 years old.

Doing skits and I'm dancing.

The world's a stage as long as it's in my living room.

♪ In the hall across ♪

Who is this kid?

He looks active.

Just a normal 10-year-old kid.

Kelsi, you have to see these pictures!

♪ They're blowing up a song when they ♪

Stop!

I think Santa looks uncomfortable.

Courtney looks like an evil doll in that one.

We both do, actually.

Add some creepy "Squid Game" type of music to that, or.

That's my tooth. That is literally my tooth.

That's actually your tooth?

Oh!

♪ Ba dum ♪

The moment I would leave the house, fear.

I'm an insecure kid.

I'm self-loathing and I have anxiety.

My mom was my compass.

She was already confident on where I was going to go.

She was like, "Even if you have to work, work, work,

you can have anything you want in this life."

I was a little jealous because

my mother was kind of a nut.

She had that Boston edge.

She wasn't very supportive, and Donna was very supportive.

And I'm like, "Moms can do that?"

Pictures of my pop. Look at that skinny prick.

Stop! No!

Yeah!

He was a brilliant guy when he wasn't drinking.

You add alcohol into the mix,

that's when the other side of my pop came out

that was unbridled, undependable, and scary.

My mom, she realized,

"He's potentially gonna damage all of us."

It was building. It was like a powder keg.

One time I opened the door and I said to him,

"George, give me your mother's phone number."

And he's like, "What? What?"

"Yeah, I want her to know the filthy,

disgusting mouth that you have

that you would talk to a woman that way."

Needless to say, he didn't like that.

I hightailed it to the kitchen.

I grab a knife and I'm literally doing this.

Like, "Stay away! Stay away."

He reached for the knife.

The house was rocking.

They were bumping into walls.

They were fighting.

Boom, the door opens and I'm up against the wall

in my bed watching this thing happen.

Hair being pulled, everybody grabbing each other,

and Darryl just like calmly sat on the bed.

He's so cool about this

that it probably helped me to relax weirdly.

That was, you know, at the beginning of a new era

'cause my dad was gonna be out of there after that.

Kelly and Darryl's real father,

he basically walked out the door one day

and didn't come back.

My father, James McCauley, he treated my mother terribly.

When she was pregnant, he, one day, just for the heck of it,

just kicked her off the bed,

held a gun to her head at one point.

She woke up and he was holding a gun

and he said something like,

"You know, I could take you out of this world like that."

He up and left one day.

He goes to the store and they think he's gonna come back

and he calls years later from California.

Part of the very first piece

of why I wanted to love my brother,

we both don't have a man in our life that's solid

and maybe we can be that solid guy for each other.

Late '70s, I met Darryl.

I was sitting on my porch on School Street in Arlington,

Darryl was walking down the street.

I knew his last name only and I said, "Hey, McCauley?

You wanna play fastball?"

I thought for sure he would tell me, "No,"

but he said, "Yeah!"

Darryl was relatively shy in those early years.

He wasn't as big of a personality as he grew into.

He was like a brother to me.

That's gonna be him in a prom.

This looks like a prom.

You got pictures I've never seen before.

- Oh, my gosh! - Wow!

I...

He was the greatest, the most helpful, most loving.

He never forgot a birthday.

He was like the perfect brother.

One day he came into the bedroom and he said,

"Would you like to go see a movie with me?"

"Die Hard!"

I just was excited that I'm going with my brother.

Get in the car, listening to music,

having the hand out the window,

doing that thing where it's like the wind's catching me.

We left "Die Hard" and we stood in the parking lot.

I mean, I get emotional about it 'cause it was a great day.

I had a brother.

It wasn't "Die Hard" that got me emotional.

You realize that, right? I love the film.

Although it was riveting and we all know it!

Mr. McLean?

From my earliest memory, loved the sound of laughter.

So sorry.

Live from New York, it's "Saturday Night!"

Watching "Saturday Night Live," watching the old Zenith,

the one that we used to have to bang the corner of.

I used to look out the living room window

and I could see the flicker of other TVs and I'd think,

"We're all probably laughing at the same moments right now."

It just felt so alive.

John Belushis, your Dan Aykroyds.

A Ritz cracker, a saltine!

Your Gilda Radners.

I have gas! What should I do?

The brilliant Martin Short.

Maybe I should just sit down and try to act kind of casual

so he'll be more impressed by me.

The laughter it brought me

broke up what was happening in the house.

I mean, the kid is on the phone. Hello? Hello?

Ah!

If I could join that, I won't feel so scared.

He said to our mom, "I'm gonna be on this show one day."

And I'm sitting there like, "Yeah, yeah, yeah, yeah."

Here's

Johnny!

Discovered standup comedy,

and then it was Richard Pryor.

But it's hard to wake up

and see the same person all the fucking time.

Steve Martin.

Dice!

These people are fearless. I wanna be fearless.

Jack and Joe went up the hill,

both with a buck and a quarter.

Joe came down with 2.50.

Robin Williams was in there.

Whoopi Goldberg was hilarious back then.

I'm just!

Sam Kinison, you were just glued to the fucking TV.

There's a dry stick in my ass!

Oh, you mean life keeps fucking you in the ass

even after you're dead?

And the crowd would go nuts! There was nothing like that.

George Carlin.

Farts are shit without the mess!

Wow!

He gave me permission to go,

"You can say something smart

and you can say something asinine."

It's fair game, including the things that I experienced.

Who hears that and goes, "Yeah, that's not for me.

I'm not interested in that line of work.

I'd rather be in sales."

Darryl and I used to talk about standup comedy,

talk about, "I'm gonna be a standup comic."

Him being like, "Wow! How do you do that?"

"I really don't know. I think it's called open mics."

Some of it I was writing from, like, junior high school up,

stockpiling ideas.

I didn't really have anything to say because I'm a kid.

But there were still pieces of truth in there.

Year one, my dad sometimes drinks a little bit too much

and he'll say, "I'm a little bit older than you.

I've been around the block a couple of times."

And then we'd say,

"That's 'cause you're too fucking drunk to find the house."

We didn't say it to him.

But when he left, it was like,

"That's 'cause he's too drunk to find the house."

He was like, "Yeah, I wanna be a standup comedian."

I was like, "Fuck! I wanna be a standup comedian."

No kids were talking like that back then.

There's one thing that I can say in all seriousness is

this is fun stuff.

It is!

What we're doing right. Walking the wild side.

One day I said, "Mom, if you support me on this,

if I do this, I'm not gonna take it halfway.

I'm taking this thing the whole way.

I'm gonna be a standup comic."

♪ That's there ♪

1990, graduated high school.

Catch a Rising Star, open mic night.

There was a comedian who wasn't there.

The name Ernest Glen gets called.

On the third time he said it:

"Where's Ernest Glen?" Three, two, one, my hand is up.

Dan goes, "Here!"

"You're Ernest Glen?"

And I'm like:

"Ladies and gentlemen,

you know him all the way from the sixth row.

Ernest Glen!"

Then into the light.

Holding onto that microphone

my whole body is in a metamorphosis.

I just did this thing.

And I ran through Cambridge, ran to a payphone.

I called my mom and I said,

"I'm a standup comedian! I did it!"

I was so hungry and ready to do it again.

Everybody in New England was trying to get on

the same six good stages.

Al & The Monkeys individual night.

Bobby, slash, J, slash, Al, slash, Dane!

How about a nice hand for Dane Cook?

Okay. How's everybody doing tonight? Feeling good?

I'm feeling good. I'm feeling good.

I'm wacky, I'm wild, I'm Kool-Aid style.

A lot of hell gigs.

A lot of bad gigs. A lot of empty gigs.

I thought I had crabs. Turns out I don't.

I got lobsters.

Slapstick.

We used to have a term for it. It's a pirate's den.

You'd walk into a pub, you know,

"What do you mean there's comedy on?"

They're turning off the TVs and people are like, "What?"

So you gotta fucking dance.

We did whatever it took.

Oh!

Oh, my goodness.

Dane was, like, making a plan from 18.

Wow!

When you first start out in comedy,

you bomb more than you kill.

You have to be kind of a mental patient

to wanna keep doing that.

The whole ride is right here.

Where I would go with it remained to be seen at that point.

My brother Darryl, his dream in life,

he wanted to be a state trooper.

Then he got the police car.

I think it made him feel important.

Was a legit undercover car.

Do you know that when he used to drive me to gigs,

if we were in traffic,

he would go, "Whoop, whoop, whoop, whoop,"

and he would make people move.

And I thought it was cool.

Darryl went into the police academy.

Unfortunately, didn't pass the test.

He still wanted to be in that world

so he became a corrections officer.

Mid '90s, while I'm doing some standup,

he's starting his career as a CO at one of the toughest,

hardest maximum security prisons on the East Coast.

Walpole State Prison, Cedar Junction.

Mentally, the job was okay for Darryl.

He was meticulous.

Transitioning to the job of a prison guard

was probably a good move for him.

The comedy group had ended

and I am languishing on the road.

One of my biggest missed opportunities in not being prepared

was "Saturday Night Live" wanted me.

He got offered "Saturday Night Live."

This motherfucker horseshoe up his ass.

Here's my dream. The show I watched as a kid.

They're replacing Adam Sandler.

He left the show and they're looking for that energy.

I went to Rockefeller Plaza the day of my audition.

I got really, really low.

Went to a payphone, called my mom.

I said, "I, I can't go in.

If I do this,

I'm gonna be one of those last-slot-on-the-show guys

and then I'll be off the show and that'll be it."

He told me, "I knew it wasn't my path anymore."

I wanted to punch him in the face!

Ended up on the road a couple years later

watching Jimmy Fallon on the show.

I'm out on the fucking road nowhere.

I'm making no scratch,

watching "SNL" after bad gigs on the road going, "Hmm!"

Mm!

My family's probably like, "Uh, fuck!"

Darryl, in that moment, was a major factor.

I was sitting in the parking lot with him

at a restaurant that we went to called Kelly's Roast Beef.

Some of my early insecurity is coming back to the surface.

The second he said, "Are you okay?"

It was like I wasn't okay.

And then all of a sudden, I-

Mm! I felt his hand on my back, like here.

He just launched into, I need to believe in myself

for that kid that I was.

It was really the most important moment of love.

You know?

If I was gonna make my way in standup,

there's only one place

that you get the validation ticket punched,

and that's playing New York City.

In the '90s, the whole thing was get good in New York,

get famous in LA.

If you didn't come in and light it up,

you might not get booked two

or three months from that mediocre gig.

It was a murderer's row on the way up.

We had Bill Burr, Therese Oneill,

a young Dave Chappelle, David Tell.

Oh, wow! Me and Bill Burr. Look at that.

Oh, wow.

Back when Bill Burr had hair.

His hair years, I guess you would probably.

I knew what it felt like to fail myself,

so there was no bad set

that was ever gonna take me out of the game.

Darryl actually was married twice.

He was married to a woman named Nicole.

Nicole lost their twins at childbirth.

About six months later she was pregnant with Cody.

Thank goodness!

This is Guy Venuti.

Darryl with his first wife and Cody.

That's gotta be Cody when he's a baby.

Wow!

Yeah!

Not soon after that, they got divorced.

He's got a son, a ray of sunshine,

suddenly after this really terrible situation.

My brother would find his purpose as a father.

After Cody was born, his relationship started with Erika.

Go with Erika.

When we met, he was extremely polite.

He held the door for me, called me Miss until I told him,

I said, "No, you have to call me Erika."

But he was really nice.

One of our first dates

was actually to go to a Dane Cook show.

I had never heard of Dane Cook.

He was following his dream.

Darryl was following his dream

of getting into law enforcement.

She was interesting.

Very different from the kinds of people that he was dating.

Who's Erika McCauley?

The minute we met her, we got a bad feeling.

Tell us about when you found out

she was a witch.

Sorry.

She was a Wicked Witch of the East.

Sometimes, like, she would even dress like a witch.

She'd be in, like, this purple and black, like, cape.

Maybe that's how she got Darryl.

A little fucking eye of newt,

a little fucking tail of snail.

Talk of her being a witch, that's fucking interesting.

Yes, I am still a witch today.

A lot of people think it's silly.

It's a spiritual journey of your own.

Where was that?

Darryl and I on his wedding day.

That was on his wedding day?

Mm-hmm. When he got married to Erika.

Interesting.

It felt very wachoo!

Like whatever she said, he did.

She obviously had some, like, spell over him

because he was never like that.

I look at everything sort of pre-Erika and post-Erika.

Pre-Erika, he was this happy-go-lucky, considerate,

tremendously funny and fiercely loyal guy.

After Erika, history speaks for itself on that one.

Mom, Kelly, Darryl.

Might have been one of the last pictures

that we all took together at Wright Street

before I left there.

- Oh, really? - Yeah!

I don't know how close Darryl was with his family.

I do know he adored his mom.

He was really proud of Dane, but Donna was even more proud.

Everything was Dane, Dane, Dane.

Understandable,

but Darryl did complain about that a little bit.

After he and I met,

he pulled away a little bit from the family.

He felt I needed him more.

Darryl spent a lot of time

as the officer in towers.

I'd be on the road

and I would call him in the middle of the night.

One night he said, "Why do you call me every night?"

And I said, "You know, to keep you company.

I feel like we should be the fathers for each other

that we never had."

About a year after those phone calls started,

I got a phone call that he was in the hospital.

Darryl had been attacked at the prison.

The inmate had sharpened the bottom of a can.

Came down with it on his head

and hit him right in the middle of the forehead.

Knocked him out. Like, boom, he's just flat out.

If the gentleman was any taller, Darryl would be dead.

When I got home, his shirt was drenched in blood.

His pants were drenched in blood.

It pooled in his shoes.

He had a concussion, was having severe headaches,

blurriness, dizziness.

That is when Dane and Darryl

decided for Darryl to go work for him full-time.

I didn't want my brother

to ever go back to the prison.

Hello, sir.

That supercharged me.

I gotta win now. Funny is not good enough.

I need to be unfucking deniable.

I wish I could tell you I had a prospectus

and I looked at it from an investment portfolio

point of view.

This was it. Ready?

If I make enough money,

there'll be enough money to give him money.

Dane offered Darryl more than Darryl expected.

The entire operation was this:

Just enjoy your life. Raise your son.

And every once in a while,

pay some bills and you'll have me sign some stuff.

And here's a consolidated list

of what I use my credit card for.

Your third party guy will come in

and help us make sure that taxes were paid properly.

From that point on, Darryl took care of all of the money.

Didn't want me involved because it was Dane.

I understood that.

When I would wake up in the middle of the night,

Darryl would be in the living room on the phone with Dane.

He was very supportive. He would go to all the shows.

They were working as a team at that point.

When I ended up in LA,

I walked into the Laugh Factory one night.

All the comics were showcase comics from that era.

Very funny, but there was no young anybody in that place.

I was like,

"I think I might stay out here for a couple months."

UCLA and all the local colleges,

they started slowly coming into my shows.

I had a few things on Comedy Central.

Three months later,

I'm filling the Laugh Factory with my fans.

When I first came here in '97, '98, '99,

I called my mom, called Darryl.

"I'm okay!

My anxiety's all right

and I think I can last another couple months."

I'm having the time of my life in LA in the comedy world.

The college gigs are getting bigger.

The checks are growing.

Why am I jumping, you know, 10 feet in the air?

It's 'cause I might be next.

I moved into the apartment in Los Angeles,

at a building called the La Fontaine Building.

I was interviewing him to rent the apartment next door.

He wasn't famous yet.

He hadn't got any of those big breaks.

He didn't know how he was gonna pay the rent.

He never told me that.

He was just my kooky neighbor for a little bit.

What came from that was family

that I discovered to this day.

Can you tell us

the first time you met Darryl and what you thought of him?

Creepy.

One word, creepy.

I felt an artificial friendliness.

He felt he had to be nice to me

because of my relationship with Dane.

I didn't bring it up to Dane. I didn't want him to worry.

We never fought, Darryl and I.

When I would ask questions,

it was pretty rudimentary, some of the answers.

He'd say,

"I don't want you to have to look at all the paperwork

that goes along with the bank,

so I just put it all on a Microsoft Word.

It's one page.

You can see what you spend. You see what you."

It was perfect.

He would handle

every aspect of every penny that came in.

Was he with Erika yet at this point?

Yes!

But she stayed pretty low-key.

She kinda stayed in the background.

As Darryl was kind of rising to power,

I looked at him as an equal.

Hello, Darryl.

Hello today.

Are you enjoying your time

here at the beach, Darryl?

Very much so. Time is almost up. Time is money.

With his camaraderie,

it was unlocking some abilities in me.

Early film work. Are we allowed to call it film work?

I mean, it barely holds up as film work.

It was work that was done that was filmed. Let's say that.

You can throw him.

He's a fucking lunatic!

Producer!

Tony's humping a tree!

That's me on the set of my first movie ever.

I played Fair Cop Number One.

You know what my line was?

Mrs. Lintz?

Mrs. Lintz!

And that was it, and the credits rolled,

and I was like, "Okay! Guess it's a movie."

"Simon Sez" with Dennis Rodman.

This is not happening!

Shit! Shit! Shit!

Aye, yai, yai!

Is the next one "Mystery Men?"

The griddle of justice.

I am the waffler.

With my griddle of justice, I bash the enemy in the head

or I burn them like so.

Ah!

He had truth syrup.

Which is low fat.

Being in the theater and being like, "Fuck, that's good."

Getting a lot of things thrown at me,

like "Full Frontal Comedy," "Premium Blend."

Oh, yeah!

But in terms of casting, I got a wake-up call.

They don't really need me.

I need to figure out how to create a platform for myself.

I bought an IBM ThinkPad computer,

one of the first laptop computers.

If you were to actually have it on your lap,

you would fucking burn your legs off.

Convenience in 11 pounds.

Next thing you know, it's like,

"You're online nationwide

with other people chatting from their computer."

All you need is a computer and a regular phone line.

They send you the software

and give you 10 free hours to check it out.

And all of a sudden, out of the blue,

comes a website called Myspace.

I was sitting in my underwear eating Fruit Loops,

at two in the morning, staring at my computer.

I put down the bowl and I went, "Hey, anybody up?"

I'm on my Instant Messenger,

which I would keep open next to the Myspace.

Bing, ding, bong, ding, ding, ding, ding, ding, ding, ding.

I had, like, 40 conversations open.

For somebody who doesn't have a math brain,

it was adding up 'cause I'm writing everybody back.

All my fans, all these gigs, they're right here.

I haven't been able to check my friend requests.

New friend requests, 12,802.

I would run home from the Laugh Factory, get online and go,

"Come on!"

And have a million people just be like, "We're here!"

God, that felt so good to go, "This is fucking it!"

I figured out the it! The puzzle!

The industry's looking for numbers.

Now I've got numbers.

I need a comedy album. I can put it online myself.

I found a company in New Hampshire

that was a fulfillment center, my first record deal.

They told me "Harmful If Swallowed"

would sell 8,000 copies in the first week.

I said, "I'm sorry, wait. 8,000?"

I was like, "I'm gonna sell more than 8,000 copies."

And they were like, "No, no, no."

They said, "The comedy album is dead."

92,000 copies it sold the first week.

I called Comedy Central Records and they were like, "Fuck!"

By the time I hit that next bowl of cereal, it hit gold.

Once he started going platinum,

everything changed.

I wasn't a movie star, I wasn't a TV star.

I was breaking through solely from standup comedy.

It's called "Harmful If Swallowed."

That is it.

People were asking for autographs after shows.

Darryl was so happy he could be part of Dane's success.

Darryl and I looked at each other and said,

"Oh, we're in for a hell of a ride."

Show me the money, Dane.

Say "Goodnight."

Goodnight!

The follow-up album,

it hit double platinum in a month.

Billboard charts, first time in 30 years,

a comedian had broken the top five in comedy albums.

The last person to do that was Steve Martin.

When they called and they said, "Number four."

I just, I mean, honest to God, I was, I, I, I just,

I'm still stunned!

Thank you, everybody. Thank you very much.

One minute you're at home

watching the MTV Video Music Awards

and then I'm presenting with Snoop,

like that.

It couldn't have been going better.

Then his mother got sick.

She was like, "I have cancer. It's bad."

The oncologist,

he said, "She has five to six months to live."

I had no wherewithal

to even consider what my life would be without my mom there.

My mom was like, "This is your moment.

This is what we talked about you wanting to accomplish,

and I want you to focus on that."

Talk about incentive!

Chris Albrecht was the president of HBO at the time.

Chris called me into his office.

"You're there, man. You're ready."

I'm gonna be on HBO.

Called my mom immediately and said,

"Your son just booked his first HBO special."

When I was a kid, I watched "George Carlin On Location."

It was in the round, directed by Marty Callner.

I said, "I wanna do an arena show in the round

in my hometown of Boston.

And what if I could get the great Marty Callner

to direct it?"

I told him. He goes, "Let's do it."

Oh, man!

You know, Darryl was standing right here when I came out.

You could see it at the beginning of "Vicious Circle."

My mom, as I walked out, I remember what she said to me.

"Embrace that which defines you."

It was so gratifying.

I'm high-fiving people, people trying to hug me and grab me.

Once I get right here, it's like a jet about to take off

and I almost went airborne.

Just an eruption!

The energy of the crowd,

19,000 people all cheering for my brother.

I mean, he was like a rock star.

It's the only way to describe it.

Okay, we have three things that we all share.

We're all gonna lie,

we're all gonna cry,

and we're all gonna take painful shits.

Not only did I know that this place

was gonna be one of the nights of my life,

I was at the beginning of a runway I was taking off

that I didn't even know where I could take it.

I would be unstoppable.

I could take standup comedy as far as I could dream it.

This spot is the very center of my life and career.

This spot!

With that energy that he has,

you get a perfect storm.

It was seismic.

Leaving the stage that night,

my very first thought, "I need to see my mom."

Brought that footage down to Delray Beach,

popped it in the VCR.

She went:

Color came into her.

My mom had said to me once,

"We can't linger in these moments,

but we fight and we keep moving."

The 200 plus arenas after that, it was:

We didn't need to seek anything out.

We were being seeked out.

I was just go, go, go, go.

I would turn on the radio,

DJs were talking about me in the morning.

Tabloids was trying to get into my love life.

Darryl kept saying, "Wow!

Wow!"

Somebody calls me and says, "Lorne Michaels is on the phone

and wants to chat with you."

"Dane, congratulations. You're hosting!"

Live from New York, it's "Saturday Night!"

That was the one thing my entire career

I was hoping I would get.

Starring Kristen Wiig!

My heart's racing.

A couple of deep breaths.

10 seconds!

And ladies and gentlemen, Dane Cook!

Hit my mark and then boom.

Yeah!

Come on!

I was actually watching it in Florida with my mom

and she's like, "There's my boy!"

What is that, like, wool?

100%.

Okay, you know what? Let me help you.

No, no! No, no, no! I wanna do this.

Oh, that feels good! Oh!

He did it twice, actually.

The second show,

the family got to go and sit in the audience.

I got to see Dane on "Saturday Night Live."

He obtained his dream.

Darryl obtained his dream through Dane.

My dad and I,

that was backstage at "Saturday Night Live."

Was it really?

Yeah, as I was doing the monologue,

I could hear him in the audience.

I almost in the middle of a live monologue on "SNL" said,

"Dad, I hear you laughing."

It was starting to feel like this is forever all the time.

I'm in!

"The Tonight Show,"

"Jimmy Kimmel,"

"Late Show with David Letterman,"

"Late Night with Conan O'Brien,"

early talk shows.

It was amazing to turn on the TV

and see my brother-in-law.

My brother-in-law!

I couldn't even keep up. Dane was everywhere.

Hollywood came a-callin'.

My first leading man role.

After "Employee of the Month,"

there was "Good Luck, Chuck."

"My Best Friend's Girl."

"Dan in Real Life."

"Mr. Brooks" with Kevin Costner.

It just kept growing and growing and growing.

Madison Square Garden!

New York City!

Madison Square Garden.

There's nothing else that you have to do after that.

The first show sold out in, like, 29 seconds or something,

so they added another one.

This little kid that grew up in Arlington

with all the nerves,

and here he is one of the top comedians in the world

at the time.

It was all working.

It felt like it was building.

I'm coming through for my brother.

Every box had been checked on

childhood-dream-come-true moments.

Going to All Star games and being in the dugout

and being able to bring his son.

We were on this incredible behind-the-scenes journey.

They became really tight

and were there for each other.

There's not much more enjoyment

than this picture right here.

At Gillette Stadium, watching the Patriots.

Darryl looks happy.

Yeah.

Yeah.

I would have done anything for him at that point.

He was such a critical part of my success.

Darryl wrote me about my dad.

"I'm sorry to hear that your dad wasn't feeling well

and needed to be hospitalized for tests.

I was thinking we could cut him a check

to cover his lost wages, say, $500.

Your thoughts, Darryl."

This is when I was like,

"Man, I'm so happy that Darryl's my big brother."

That's all Darryl really wanted!

To have Dane succeed.

When the wave started going down a little bit,

that's when our mom passed away.

My mom would succumb to colon cancer.

She said, "Don't worry.

I'll always have the best seat in the house."

You know?

I knew that she didn't want me there when she passed away.

She knew Courtney was stronger for that.

She turned to Courtney, she said, "I love you so much."

And she passed away.

Darryl, I think, was the first one to fly down.

I never saw him, you know, cry even when our mom was sick.

He always stayed pretty, very calm.

However, I don't wanna say that

my mom didn't fully trust Darryl, but before she passed,

she did say to Dane like, "You watch out for your brother."

She had this inkling about something.

She had a sense

and she didn't wanna rain on the parade 'cause I was happy.

I'd say, "No, Mom, everything's good.

He's doing great. We're great."

"Okay! Okay.

I just wanna make sure everything's all right, you know?"

Even against what she told me and warned me of him,

she just wanted us to have that camaraderie.

Her dying wish, "Please,

the four of you be there for each other."

10 days later, I sat with my dad and he was like,

"I don't even know how to say what I'm about to say.

I have cancer.

I've been told I only have a few months to live."

Dane's father died not long after.

Although he was Darryl's stepfather,

he was more of a father to him than his biological dad.

Darryl took it hard.

It was nine months of moments of, like,

nothing felt worth it.

All this didn't feel worth it.

Dane was angrier.

He was depressed.

It was like his reason for going on was gone.

Darryl changed.

He got depressed too, and he and Dane weren't as close.

As my business was expanding, I bumped him up in a raise,

125,000 a year to $150,000 a year.

God, he paid him that much?

That's quite a gig.

When your boss is your brother, mm,

I'd do everything in my power to keep that job.

Darryl's job got busier,

but he also had much more access.

He did become power of attorney as well for Dane.

I did not know that

Dane had given Darryl power of attorney over anything.

I would have recommended against it.

If it was a full power of attorney,

that would open everything to Darryl.

I was starting to feel something

that I couldn't really identify.

Him kind of positioning

who I shouldn't be doing business with.

Like, really, like, adamantly wanting me to pull the plug

on certain places.

"New York Entertainment is no longer an asset

to Great Dane Enterprises.

They've become part of the problem."

All of this is, like,

"They're asking me too many questions."

"It is for these reasons I seek to terminate

our business relationship with them effective immediately."

Almost like when they started getting so hands-on,

he was like, "You gotta get rid of these guys.

They're overwhelming.

They're confusing the brand, the business."

Little things that I'm starting to say to him, things like,

"Hey, when we do business,

nobody else is helping you, right?

Erika, your wife, like, nobody?"

"No!"

"Not even a staple on a page, Darryl.

I don't want her involved in anything.

This is us, right?"

"Yeah! Yeah!"

"Okay, good. Good."

Why am I asking that question?

He had a nice house that he had bought outside of Boston,

but then he had another place in Maine.

Okay, well, maybe she's doing well

or maybe he's invested in some way.

I remember saying to Darryl,

"This is crazy. Good for you guys."

And he's like, "Yeah, you know, Erika does very well."

Darryl and I started to talk more

and more about what happens when Dane isn't so popular.

It was one of the reasons we started businesses up in York.

I asked him once, "How much money do we actually have?"

He said, "Enough to live the life we want."

I was starting to tell him,

"I'm gonna wanna move my business to Los Angeles.

Whatever job title you wanna take, pick a title,

nothing's gonna change.

You don't have to move out here.

At some point, Darryl,

you're gonna just send the file cabinet.

I'm hiring this guy, Richard, Richard Feldstein.

I like these guys. I've met with them.

I'm doing this, Darryl."

I'm known within the industry

as being someone who deals with messy situations.

They got us on a conference call,

Darryl, Dane, myself, and his entertainment lawyer.

I started asking Darryl some questions.

Somehow it came around that he hadn't filed tax returns,

but he had filed antitrust paperwork.

I've never heard of that in my life

except for public companies that are acquiring others.

The questions we were asking Darryl were technical

and his answers were nonsensical.

After the call, the business lawyer called me and said,

"You know, we'd like to bring Dane in."

I said, "Dane, we need to really look at all your stuff."

I started having conversations with Darryl saying,

"I think I should buy a home.

It would feel good to have a place that is mine."

When I found the home, the view was Nakatomi Plaza,

the building from "Die Hard."

We sat right here.

Darryl and I sat right there, looked around, and I said,

"Can I, you know, can I do this?

This feels like it could be home."

With his arm around me, he said,

"You've earned it. You can do it."

This is where he clearly knows

there's a wall of fire collapsing down on me,

but he was helping.

So here's this guy saying,

"Just embrace and enjoy your home,"

and we're months away from a firing squad, is my brother,

but you've got the blindfold on you peak and here it's him.

All Richard asked was,

"Just have Darryl send the file cabinet."

Darryl was just like, "Whatever you need, it's coming.

I'm putting it all together. It's coming. It's on its way."

He had no problem with it when he and I discussed it.

He just didn't think

the firm that Dane had chosen was a good fit.

"Yeah, look, I'll get you guys everything."

Never sent us Jack.

The only info we got from him was via Dane.

There were some tense phone calls.

Darryl would hang up the phone and just start mumbling,

"He's not listening to me."

Then Darryl told me,

"Well, I'm not going to have a job with him anymore.

What am I going to do? I don't know anything else."

Darryl wrote Dane a lengthy email

attempting to convince him to leave his business as it was.

According to court documents,

there was an email showing that you were drafting, editing,

and making comments on that letter before it was sent.

He wasn't happy with

the way the letter was coming out.

He had me take a look at it

to just lay out the evidence that he had

in order for Dane to make the best decision.

Do you remember what Dane's reaction

to that letter was?

I don't think Dane appreciated it.

The day before Thanksgiving, he said, "I booked a flight.

I'm coming out to meet with you

to talk to you about why I think."

I said, "Darryl, fucking stop! Cancel the ticket!"

I actually heard myself and I was like, "Why am I so mad?"

I did hear him and Darryl yelling on the phone.

At that point, Darryl said, "Fine, do what you're gonna do."

The last three words Darryl McCauley ever wrote to me

as the person I knew was, "To the future."

That's it.

That was my goodbye letter from the brother I thought I had.

Richard Feldstein writes me an email, basically says,

"The files were supposed to be here this week.

They're not here."

I wrote Darryl again.

He said that he had a family emergency, he was on the road,

and that he would get back to it after the weekend.

Was like, "Family emergency?"

I tried to call Darryl. Nothing.

I tried to sleep, feeling like,

"Something's not right. Something's not right here."

I sit up in the morning and I say out loud,

"I think my brother stole all my money."

And the girl that I was seeing at the time was like, "What?"

I called him again that morning.

No answer.

Pacing around my room,

"I think my brother stole all my money."

He had this gut feeling,

and then it all started.

There was a Bank of America

on the corner of Crescent Heights in Santa Monica.

I could walk to it. I ran down there.

Standing outside on that morning,

having to walk inside and say,

"Can someone please help me to look at my accounts?"

The bank manager comes over.

"Listen, no, no, I understand. Like, whatever you need.

In fact, let's go in my office."

And I'm like a caged rat in my mind.

"I need to look at, ah, it's Great Dane Enterprises,

the name of my company.

Can you just look that up?"

"Okay! What's your federal ID number?"

And, "All right. And I'm sorry, what is it again?

Uh, okay.

Um, no, that didn't. You have another one?"

It's like, "Do I have another federal ID number?"

I'm like, "Yeah, okay, this number."

I've got stuff in my phone that Darryl has sent me.

"Put in that number."

She's like, "That number isn't working."

Whatever she was seeing was not good.

It was like...

And then she looks at me and she goes,

"I know you, but I can't help you unless I have this,

the credentials.

You understand, right?"

She goes, "I'm gonna go get some water.

I'm gonna get up and I'm gonna leave.

I'm gonna go get that."

She's saying, "I'm gonna get up and leave

so you can walk over and sit in my desk

and look at my computer."

"Yeah, yeah. Okay, good. Yeah, yeah. No, whatever.

I'll take water. I'll take coffee. I'll take fucking both.

Anything. I'll take an empty cup. I don't give a fuck!

Just leave this room, please, right now. I get it."

And I did run around and sit in her chair.

Whatever's open, it's like three or four different things

that she placed.

I know what I don't see, which is a lot of numbers.

It's crumbs!

Crumbs of currency after earning what I believe to be

in the tens of millions of dollars.

I think it said, like, $111,000 or something.

And then another one that was open, it was zero.

Mm!

It makes me emotional. It's just like, "Wow!"

To do that to your brother.

He wanted Dane to have nothing.

It's like we lose our mom, our dad, and then this happens,

and it's like, wow.

I felt like I was done.

I felt like my life was done.

That killed Dane.

That absolutely killed him.

It was horrifying for him.

The business lawyer and I both said,

"We should go to the bank ASAP."

Requested all the statements for the last 10 years.

We worked up from what little records

we could get from the bank.

We needed Dane to look at this information himself.

In particular, copies of checks.

Sitting in this very conference room,

we presented a certain check to Dane.

Rich Feldstein, my partner,

asked him if he recognized the check.

It was a large amount, and one that we thought was unusual,

made out to Darryl McCauley for $3 million.

We handed this to Dane

and this is the very first check he saw.

Clearly, there was just stunned silence.

This was a 12 on a scale of 1 to 10.

For this amount of money, he had no choice but to pursue it.

At that point,

Joe Zwicker became our main point of contact.

What Dane did in authorizing me to take this case

was to let slip the dogs of war.

Once he started, there was no going back.

I told him what the strategy would be.

I personally couldn't bring Darryl to justice,

but the federal government could,

the state of Massachusetts could.

Within hours we had the brass of Massachusetts calling up

where everybody was not saying yet

what I was waiting to hear.

"Your brother is a thief!

He has wiped you out!"

Yep!

Here goes Robert.

Rick Grundy told me we had a meeting

after normal business hours.

Something was up. There was nobody around.

They wanted him to come in without having people see him.

Sitting across the table from him,

"Tell me what happened."

Darryl's character profile presented itself.

He was selling T-shirts

and all the sudden he was managing a movie star's money.

The most obvious thing,

$3 million in cash walking out of the bank.

The gentleman who made the money is sitting here,

saying that he never authorized somebody

to walk out with three million.

You and I could figure that one out.

My pursuit would be to put his brother in jail.

He indicated very forthrightly

he was there for us to do our job.

He's like, "Have you talked to Darryl at all?"

And I said, "No!"

"I'm trying to find him.

He's not returning my calls or texts or emails.

I'm really nervous.

I think he might have stolen some money."

And I was like, "What?"

"Kelly? Yeah, I was wondering, have you seen Darryl?"

"No, I haven't talked to him for a couple of weeks."

I'm like, "What's wrong?"

He goes, "I think he, he took money.

I think he took a lot, a lot of money.

We're looking for him now."

Where is he?

What's he gonna do?

What has he done?

Who else is involved?

How does this end?

I'm in one of those mysteries

when you'd watch a show like, "A family with a secret"

and you'd always be like,

"Damn! I wonder if my family has a secret."

My family did have a secret.

We placed Darryl, Erika as well,

under electronic surveillance,

through the use of GPS devices, phones, cars,

where they work, where they live, what they do.

It wasn't long into the investigation

that it became abundantly clear

that she was every bit as much involved as Darryl was.

It appeared that both were benefiting from the money

that was taken.

Everybody has thought that I am 100% guilty.

In reality, the only thing I'm really guilty of

is being gullible and trusting my husband.

Erika, are you telling us that

never at any point did you know

that he was stealing his money?

I never knew that Darryl was taking Dane's money.

I did not know until after the fact.

I would get an allowance from Darryl

and if I wanted to make a purchase, I asked him,

"Can we afford this?"

He would say yes or he would say no.

I didn't take care of the money,

so I went by whatever he said.

I just hate that you guys see this side of me.

It isn't who I am,

and I mean this when I say I was a gullible idiot.

The forensic analysis that we did

showed a crime that became more brazen

and increased in size as the years went on.

Initially, withdrawals for $20,000

became withdrawals of $50,000, wires of $100,000.

Brazen thefts that grew over the years

just as Dane's success grew.

Erika had a company called Witch 1 Productions,

which appeared to be put together

for the purpose of trying to wash some of this money

and funnel some of the stolen funds through.

So what's interesting is

the business activity payments made to Darryl.

Here's a check for 70,000 in September of 2004,

but on the same day there's a deposit

which corresponds into Darryl

and Erika McCauley's B of A joint account.

These are photocopies.

I remember looking at this

during the forensics audit with Richard Feldstein,

Thomas Kingsley.

September 30th of '04, 22,000.

This is $28.

He just randomly stole $28 in a check.

That's almost more disgusting than the 22,000.

You son of a bitch.

Again, like, $31,660.17.

Round up!

780,000, pay to the order of Darryl McCauley.

995,000.

Here's a million, five,

but one couldn't really see how it was used.

61,000.

3,780.

20,000.

This one's 100,000.

And this one's Witch 1 Productions,

so that's Erika's company.

That's how the trail matched the money being stolen

and how the money was used.

There weren't even days in between.

Often there'd be a check out of Dane's account

and the same day back into the joint account.

There wasn't even an attempt to try and hide it.

I'm getting phone calls from

Richard Feldstein and Company,

"We're gonna try to stabilize things right now

and you can't buy that house."

I went into that meeting and I said,

"Let's start, and I am buying that house."

They were like, "All right.

We'll get to the house thing later,

but let's let's try to unfuck this moment right here first."

"Richard, what do I have?"

Said, "What about in the stocks stuff?"

That was some of the only money he had left.

Darryl hadn't let him go completely destitute,

but he was darn near close.

I said, "How much is that?"

And he was like, "That's about 340,000."

"Okay. I have one other question.

Is there anything else that's about to hurt me?"

He was so professional.

He was like,

"Well, there is the question of the unpaid taxes."

"Okay. Ah, how, how, how much did he not pay?"

It's about $6 million in unpaid taxes to the IRS.

He didn't pay my taxes for at least six years.

Tacked on with interest that's also owed.

So not only is there no cash to pay the tax,

but there are no business deductions

so the income tax bill is much larger

than otherwise would have been at hand.

Dane could get some tax deduction for the theft loss,

but we needed a case against Darryl that's proven

and not just the allegation to go down that road,

and the clock was running.

At that point,

Darryl probably knows his number is up.

He knows that Dane is going to discover the fraud.

The search warrant was imminent,

an arrest warrant was imminent,

and that arrest was imminent.

Darryl knew he was toast.

He went on the run.

He was on his little run.

Just him in a rental car

with a few million bucks in the back.

You know? A run.

Not just where is Darryl it was, "Where is Erika?"

On my end, not only was I talking to Courtney,

talking to Darryl's sister, Kelly,

I was trying to get from everybody,

"Was I missing something?"

Called his then ex-wife being like, "Where is he?"

She's like, "I think he's driving somewhere.

I think he's on the road somewhere."

We knew where they were.

We were able to track him.

Darryl was traveling across the country.

Was he squirreling it?

Was he hiding it in different places?

Stockpiling this money?

It became, "Oh, this is so fucked up

that this is happening to me,

but this is kinda entertaining."

I feel like they were stopping in different spots

to stash money.

They weren't just driving to drive.

There was emails and texts that went back and forth

where they talked about traveling the world,

emails about old money in Ireland,

"Now that we're old money in Ireland."

The ticking clock was done

and now we were in this phase of:

Who's gonna get to who first?

Dane wanted his paperwork.

Darryl had his paperwork

and Darryl wanted to get it to Dane safely.

He decided that we were gonna take a train trip.

I had asked him why he didn't want to fly

and he said that he had too much paperwork with him.

Fees for luggage were so high at that point

that he felt more comfortable taking a train.

So we set off.

We made it to New York.

We made it to Washington, DC.

We got on a different train.

I was so stomach sick.

I was throwing up everywhere.

And so we got off until the car rental place was open.

We piled everything in the trunk and in the backseat

and we were off.

Has she seen a plane?

Does she know what planes carry?

"Too expensive, but we'll pay for the petrol

to drive it across the country.

We weren't running. We were actually coming to you."

Oh, my god!

It wasn't until the phone calls started

that I knew he had not told anybody.

He said the only one who needed to know was Dane.

Then Darryl told me his phone wasn't working.

He had to start using payphones.

He refused to use my cell phone.

Looking back, he was obviously hiding something from me.

He said, "Honey, it's nothing you need to worry about."

I said, "Okay. You've got this covered.

You've got it covered. I'm not gonna ask anymore."

Erika,

was there cash with you guys on that trip?

Darryl had suitcases and boxes.

He told me there was paperwork in them.

I never even thought that there would be money in them.

I would have freaked out.

Who in the world travels with $3 million in their car?

And we left that car in parking lots.

I finally got a hold of him. Darryl was in Utah.

I said, "Darryl, what the heck's going on?"

And he's like, "What do you mean?"

"We're all trying to call you and email you, text you.

Like, why aren't you returning Dane's calls?"

I said, "Darryl, when you hang up with me,

will you please call Dane?"

He said, "I love you, Courtney. I will."

And that was the last time I talked to Darryl,

and he didn't call Dane.

I'd spoken to Cody, his son. He's 15.

Cody called me up.

He says, "Uncle Dane, can I, can I tell you something?"

"Cody, you can, you can tell me anything.

You can share anything you want with me."

"I was on my dad's computer a couple months ago

and I wanted to search 'How to break in a baseball glove.'

When I typed 'How to,' it said,

'Hide a lot of money.'"

This kid's just starting out.

And now add to it, your father's probably gonna get arrested

on the local news.

He'd also called Cody a couple times

and then Cody and his mom would kind of tell me.

He was just lying to them and say,

"Ah, I'm on a business trip."

Nobody had realized he was in California.

The authorities were calling me up.

"You need to be careful. He's near you right now.

We're tracking him."

They were adamant.

They were like, "No, man, no.

What we know, you need to protect yourself at all costs.

This guy basically made a beeline across the country

from Massachusetts to you."

Dane honestly thought that

they were there to hurt him.

I got around the clock security

sitting outside of my place.

They were in a desperate attempt

to get themselves completely out of the frying pan

and the fire, take me out of the picture,

then would they and were they thinking of doing that?

I don't know.

Like a weird dream that you wake up from and go,

"Oh, that's nothing like the life that I live."

It was bizarre.

Knowing that Darryl was that close to where Dane was,

do you think Darryl ever had

any thoughts of physically harming Dane?

Oh, god, no!

Darryl was not the physical type.

He would not have hurt Dane.

He would have hurt himself before he would have hurt Dane.

About four or five days after he was missing,

he left me a message.

I actually have it on my, ah, on my phone.

Should I play it?

I just want you guys to know

this is the first time I've heard his voice

since the last phone call I've had with him.

Here you go!

All right!

Dane, it's your brother. What is going on, Dane?

I just heard Courtney and Nicole telling you that

the FBI is involved with something.

Dane, what happened? What have you done?

Oh, my god! I'm so scared right now.

What, what have you done?

What is going on? Why are you doing this to me?

Why aren't you answering your call?

Oh, my gosh. Please call me.

Please call me.

Now that's acting.

He was full of shit.

That's not the man I remember.

It's not the friend I remember.

"What have you done? Why are they after me?"

Nobody listened to that and went,

"We should hear him out."

It reminded me of "Fargo" so much.

That scene in "Fargo?" It's that.

Yeah, Wade, I, it's Jerry.

Wade, it's Jerry, I, we gotta talk.

It's something. Aw, geez!

Hello?

Ah, yeah. Wade Gustafson, please.

"I'm scared, Dane. I'm scared."

I wonder if he hung up and went, "Ah!"

Like, "That'll keep me safe.

Now they'll think it's all him."

It's the least impactful thing in our entire relationship

was him leaving that message.

And he didn't leave a number so I couldn't even call him.

So where?

You don't leave a callback number.

Oh, my gosh. Please call me.

Please call me!

If I had heard that,

I would've thought that Dane was screwing over Darryl.

I can tell how afraid he is.

Panicked.

It hurts my heart.

He never showed any of that to me.

Do you wanna take a second? No? Okay.

What are you thinking right now?

How stupid I was.

I was so stupid and so trusting

and it has ruined my relationships today

because if I can't trust my husband,

who can I trust?

My stupidity, my gullibility.

It's a humiliation because I was so stupid.

I need a minute.

You can go take a minute.

That's it.

That's the last time I ever heard anything from him

was that message.

On the way home,

we started getting a lot of phone calls

from Darryl's family.

Kelly was screaming over the phone

that Dane was calling the FBI.

I started to panic.

"What did you do?"

That's when he told me,

"Well, Dane had me take $3 million out of the bank.

I left it at his house."

"So why would he call the FBI on you?"

"I don't know."

"Call him! Talk to him!"

"No! I'm waiting till we get home."

All I knew at that point we needed a lawyer.

I didn't know if Darryl had done something wrong.

I didn't know if Dane killed somebody

and he was going on the run.

Dane had been acting so unusual,

I didn't know what to believe.

Then Kelly saw him at a Christmas party.

After they had gone missing,

Darryl and Erika stopped by the cousin's Christmas party.

Kelly took Darryl into the other room and said,

"You wouldn't do anything to hurt Dane, would you?"

And Darryl's like, "What?"

With his big eyes looks at me,

"No! I would never do anything like that.

Why would you think that?"

Erika came along and swept him away.

Leading up to the new year, they closed in on him.

And then back in Massachusetts, he was arrested.

Dane Cook's brother, his half-brother, I should say,

apparently embezzled millions of dollars from the actor.

Whoa!

This is apparently skimmed off the top

from company checks that he wrote to himself,

all this while he was being paid by Dane Cook

$12,500 a month.

It got so bad that at one point,

the half brother wrote out a check

for $3 million to himself.

The night he was arrested, I was up at York Beach.

My employee came upstairs and said,

"Erika, you really need to come see these gentlemen."

In that moment,

I knew Darryl did something wrong.

Erika was still in York, Maine.

The police go to serve a search warrant.

It was a nice condo, overlooking the beach.

We started a systematic search.

You would assume the appearance of the interior

would be a little more put together, little more upkeep.

I think that they said it was a pig sty.

In the kitchen, I found her pocketbook.

Inside was over two grand.

There was also two deposit slips.

One was for 50,000, the other one was for over 200,000.

I've never seen these.

Oh, wow! This is interesting.

So this is a bunch of crappy jewelry, money in a drawer.

I went into a room

and I noticed there was a picture on the wall

that just didn't look right.

Doesn't fit.

I went over, took the picture out.

Sure enough, there was the wall safe.

We asked Erika for assistance. She comes in.

She tries a couple times, it won't open,

and eventually the beeping stops.

If you try it so many times,

the safe has a way that it shuts down.

You can tell she's screwing around with it.

While I'm in the room,

I find directions of it, how to reset it.

It says, "A nine volt battery.

If you put it on the numbers, it'll reset it."

She went to the kitchen, comes back a brand new battery,

put it up there.

I said, "Put the number on it."

She tried it again, put it in and it popped open,

swung the door open,

and there's just piles upon piles of cash stuffed in there.

This is all $100 bills, front to back, side to side,

stacked up, maybe two feet by two feet.

Yeah, and I'm like, "This is not normal."

I don't know about your house,

but that's not how my house operates.

I like that they included

the picture of the nine-volt battery, just so we know.

This did it!

Thank you, Duracell.

Once we cracked the safe,

her demeanor didn't change as much as I thought it would.

The last time I had seen it,

there wasn't nearly as much money in there

as there was when they opened it.

I was pretty shocked.

I actually had to sit down on the bed.

We set up teams.

You would count, I would count, then we'd switch.

It was tedious.

My god, it took a while!

The little round table in the kitchen

was full of stacks of money.

We stacked it in the middle

and then down in a shape like this.

Total was just over $800,000 in $100 bills.

He did not trust banks,

so we always had cash around the house.

I knew we had money in the safe.

He said that was for emergencies.

I did not know we had that much cash.

"Our money,

but we've hidden it because we don't trust banks."

I don't buy it for a second, obviously, and no one should.

Where's the rest of the money?

Where's the millions and millions

and millions of dollars that are missing?

It was New Year's Eve, watching the news,

showing my brother coming into the courtroom

with his handcuffs on.

He just had a blank look on his face.

He seemed to disassociate himself from the whole thing.

He managed to B-S his way with his brother for five years,

maybe he thought he could B-S his way with the courts.

I can't imagine

what his attorneys would have possibly had as a defense.

I thought he was innocent.

I knew I was innocent,

but I also knew that if he was guilty, I benefited.

I realized if Dane wanted to pursue this,

he was going to make sure that I was in jail too.

What I saw from Darryl was almost like an anger

that Dane was pursuing this against him,

that he was entitled to something.

He had been hurt somehow by Dane that justified his actions.

Darryl felt like he was a creative force

in what was happening and he was getting peanuts for it.

The hardest thing about prosecuting white collar criminals

can often be they don't think what they did was wrong.

Your world comes crashing down.

You have to create a new world.

Nobody's gonna do that for you.

How am I going to get up from this?

The scraps he left behind,

I used that to then put together an independent tour.

That independent tour was me personally calling up arenas.

Month to month, I was doubling my money,

and I got a couple of partners to come in.

By the end of the year,

I think we ended up doing like 81 dates or 88 dates,

somewhere between there.

I was earning that year and paying the IRS.

I said to Richard Feldstein and Company,

"Keep paying it back until that's paid

and then I'm gonna keep going."

My whole goal was:

By the time I see him in the courtroom, I'm gonna be fine.

Weeks later, I started to panic.

Darryl wasn't going to be coming home.

How was I going to take care of myself?

How was I going to take care of the house?

I was working on self-preservation and fear.

That was the beginning of my biggest mistake of my life.

I got a phone call

from a cousin in Florida who came forward and said,

"Listen, Darryl and Erika had been talking to our family

for some time about investing in some of our restaurants

down here in Florida.

She's calling me,

saying she wants to bring some money to invest."

This particular individual

agreed to do an undercover sting operation with us,

wear a wire, and prompt Erika to follow through

with her plans of investing stolen funds.

I told Darryl about the phone call.

He said, "You need to bring him money."

Little did I know that

the family that I thought was helping me

was actually working with Dane to set me up.

The police officers,

they believed that you were communicating with Darryl

with coded messages.

Well, yeah!

Darryl had to tell me where to find the money somehow.

We couldn't talk openly.

How much of where that money was hidden

did you know of?

None of it.

He was talking about nail files and bathroom tile,

make sure the grout is clean on such and such a tile.

Then he started getting more specific.

Realized what he was telling me.

We're electronically surveilling Erika

at this point with a GPS,

and we're able to discern that she went to the jail.

She visited with Darryl.

I wanted to talk him out of it.

I knew I was going to get myself in trouble.

Upon arrival in Florida,

she met with this individual in his home.

She walked into the kitchen.

She put down a vacuum bag.

When she unzipped it, she looked up and said,

"I brought 400,000 instead."

Originally,

you were gonna bring down 200,000

and then you brought down 400,000.

Why did you change it?

Kevin suggested if I brought down a little extra,

he would be able to hold onto that for me.

Of course she knew. She knew!

Dane wasn't paying Darryl that much money.

You cannot tell me that you think this is legit, legit pay.

"Oh, I've got a bag of 400,000 cash.

There's more where that came from and it's all legit

because Darryl's a go-getter."

Who knows when, maybe not at the beginning, probably,

but she knows.

I can't say it enough.

We had shovels, we had tools.

If there was something in that house, we were gonna find it.

The home was somewhat of a movie scene in and of itself.

When we got to the freezer

and found that they had about

20 Tupperware containers of spaghetti sauce.

Wrapped up money in Tupperware containers.

It had gravy in it, as you used to call it.

Put one under the hot water

and there were bricks of hundreds

in all the spaghetti sauce.

I'm sorry.

In the pasta sauce, of course.

Where else would you put the money?

I didn't know that. This is blowing my mind, dude!

This is a thing they're doing!

We found cash everywhere.

Tied to a string, down a heat vent.

We pulled it up, caught some money.

It was in the attic.

Under the?

Insulation.

And in weird places.

Behind a tile in the bathroom, a bed frame of a kid's bed.

Always check the mattress.

It must have been exciting for them to-

Maybe they hid it from each other.

They played a game.

The condo in Maine,

in a Bagel Bites box in the freezer, $90,000.

They found cash behind the bathtub.

Behind the bathtub is safer than fucking Bank of America?

And you believe that, you fucking Soprano wife?

I just want to reiterate this is all my opinion.

I'm speculating, but it's fun.

Right in front of us was this giant potted plant.

He goes, "Hey, has anybody looked in this plant?"

I took out of a block of knives the sharpener

and dropped it in and it went about halfway down

and was solid.

We kicked it over.

Underneath the plant, underneath all the dirt,

was 150,000 in cash all sealed up.

If you're keeping track at this point,

they are north of 10 million dollars

that they have found in stolen funds.

Stolen funds, by the way, is code for my fucking money.

We weren't finding those kind of assets

that we would expect in that level of theft,

which was perplexing until we looked at the credit cards.

If you sat them down and said,

"What did you spend the money on?"

They wouldn't be able to tell you

because they're just spending money.

This is the use of fraudulent disbursements, 2003 to 2008.

Lakeworth Rum Shack Bar & Grill got 50,000.

Herb Chambers, Honda of Burlington, 42,897 bucks.

There was, like, 175,000 in improvements, right?

- Right! - Renovations to the home.

$18,000 for stereo surround sound.

Stereo!

Oh, now it makes sense,

'cause you want the bullshit coming from both sides.

Flights to Baltimore to see the Red Sox play.

In third!

Go, Socks.

They like to vacation at the Mohegan Sun Casino.

They had a timeshare in St. Kitts.

Vacation in West Palm Beach, Florida.

They literally just blew through

hundreds of thousands of dollars

in luxury items, travel, and gifts.

I think the one name nobody is gonna be expecting

is Garth Brooks.

What? They spent money on Garth Brooks concerts?

They, really?

I would say, "Ooh! Can we go?"

And he'd say, "Okay!"

Darryl never denied me anything.

They had purchased Cadillacs.

Cadillac XLR.

I loved that car, that Cadillac.

I was shocked when Darryl had me put it in my name,

but I was proud.

I mean, who buys two Cadillacs at once

if you can't afford it?

I got a suitcase

filled with thousands of pieces of cheap jewelry.

I like the shiny things.

He would buy me rings. He would buy me necklaces.

Were you aware that

the jewelry came to $522,000?

I can, I can see how it got upwards of over 500 grand.

I like expensive things.

Credit cards I remember in particular were outrageous.

I would not have any idea how much we spent

even on just the American Express card.

It was 1.5 million.

Holy shit!

That's a lot of money.

The only thing I can say is

I was under the impression we had that,

and that's why you can't trust me

with a credit card.

That's where it is.

In the Atlantic, and then upstairs were the restaurants.

Right.

$360,000 on charges for her businesses.

Ballsy.

It is true that I was getting money from Darryl

to start my businesses.

I did not realize or know that he was stealing it from Dane.

Did you realize it was coming to 364,000?

Darryl told me to keep it within 500,000.

I was really proud of myself

because I came in well within that $500,000 limit.

Is this real? Is that a real number?

Is this just Amex?

Oh, my god! I need a sip of tea for this one.

Excuse me!

Um, anybody wanna take a guess?

Five million.

Five million.

I never knew that about the Amex.

That's bonkers.

That's crazy!

Erika was pleading not guilty at this point.

So if you need a laugh at this point in the documentary,

I got you covered.

The frauds at least began as early as 2004.

You begin to see withdrawals in amounts

that for no relation to the services

that Darryl was providing to Dane.

Came to an amount of theft of $12 million.

I would not lean on any firm standing that

that's 100% accurate.

I think it could waiver upwards of, you know,

another 3 to $5 million.

What is a mystery still to this day is

there were many cashier's checks taken

without knowledge as to what the money was used for.

What we would call unidentified disbursements,

to the tune of $2.7 million, 338.

The last evidence of anything

was the gouging of the last $3 million.

Out of everything that he took,

I really always seemed to focus on that.

This is the last check.

Interesting.

November 24th,

$3 million, pay to the order of Darryl McCauley.

Signed my name, which is weird

'cause I don't see my name on any of them actually.

The note, the memo says "DCFM."

D-C-F-M?

Like, Dane Cook, fuck your money.

What the did that mean?

Dane Cook.

Darryl's best friend, Guy Venuti had a guess.

What do you got?

Dane Cook fucked me?

I mean, could it stand for something else?

Don't care for family members?

I don't know at this point.

Dane Cook fucked me. Mm!

No!

Well, DC would be Dane Cook.

Huh!

Could also be Donna Cook, something. I don't know.

I don't know what the M is.

I think it's Dane Cook fuck me, but...

If anybody out there has an understanding of it,

then feel free to opine.

It's just another mystery amongst mysteries.

On the $3 million check was D-C-F-M.

Dane Cook fun money.

Seriously, that is what it is, because they used to tease,

"I'm going to have some fun money now."

We all would say it.

Dane Cook's fun money.

Darryl's fun money. Erika's fun money.

This is how brazen he was.

He went to the State Street Bank of America.

He walked in with a check from him to him,

endorsed for $3 million.

And he said to that bank manager, "I need the cash today."

And he put $3 million in duffle bags and he walked out

and he put them in a rented fucking SUV.

♪ Oh, oh ♪

Was the point to just bury me alive with nothing left?

With that action said, "Fuck you! I'm taking everything."

It's not just money.

It's blood, sweat, and tears for the past 25 years.

That's what it represents.

What's up, 2009?

You're going to be gone in about three hours.

And I will not miss you.

There were some highlight moments in my year

and I will from a distance

appreciate some of the things that you've done.

Now I have to ask you to leave.

You know where the door is.

The state wanted to draw this out

until Cody's 18th birthday.

Then they would put him on the stand

and grill him without family in the room and only press.

I didn't think he could handle it.

I know I couldn't have handled watching it.

So when the judge asked me if the charges were true,

I said "Yes."

The phone call came in, "He's gonna take the plea."

Okay.

Good. I wanna be there for that.

I had to read what is known as a Victim Impact Letter.

I only had one request for the court.

"I do not wanna be called a victim."

I was shaking.

- All good! - Thank you!

This is my brother.

I have to go see that guy.

Will he love me?

A little bit.

But knowing he won't.

This is it, here.

Oh, wow.

Wow! This is the spot. This is exactly the courtroom.

This is the...

Hmm!

I sat right behind him about maybe five rows back.

I hadn't seen his face in two or three years.

He's right here.

And then walking right over here to the podium,

I'd asked somebody before, I said,

"Please make sure the podium is close to him.

Put it right down his throat."

Took a deep breath and I felt him looking,

but I just didn't look.

He had turned entirely to me.

He was 10 feet away,

but it felt like he got nine inches from me.

Had my letter.

I didn't wanna look until I got to the part about,

you know, Cody.

You know, your son.

Look at us. We're the result of our fathers.

We were supposed to be examples of something new

and improved, and you have fucked it up for him.

I'm looking for anything.

One iota of remorse.

A shark with beautiful blue eyes.

I didn't know him.

My brother was not in the room.

Makes me angry.

You've now gone ahead and had no remorse whatsoever.

He wants to go,

"Hey, I'm willing to forgive you if you just go,

'Fucking sorry, bro! I lost my mind.'"

That part scares me.

The Darryl I remember

would never have done something like that.

Ever!

I almost feel like I missed something.

Finished my letter,

and then I went and I took one extra step towards him,

almost looking down at him.

Nothing!

Nothing.

There was just no empathy.

His son, his mother,

his friends, his wife,

himself, his brother.

Nothing.

Darryl was convicted of 27 counts of larceny,

three counts of forgery,

one charge of embezzlement by fiduciary,

one count of conspiracy to commit larceny,

and one count of uttering a false check.

Darryl received five to six years in state prison,

followed by 10 years of probation.

♪ Oh ♪

Life has its own comedic stylings.

What were the odds that

the prison that I would put Darryl in

was the same prison that I took him out of?

Cedar Junction, Walpole State Prison.

Former corrections officer.

That's where he would remain for a few months until,

for his safety, they moved him to another location.

I pled guilty to two counts of larceny

and conspiracy to commit larceny.

I was sentenced to 2 1/2 to 3 years in state prison.

That's where I spent the next two years

and eight months of my life.

Darryl did not serve the full sentence.

I believe he served somewhere

in the neighborhood of 3 1/2 years and he was paroled out.

Him and Erika divorced.

He's working as a FedEx driver delivering packages.

If you're missing any packages,

I think I know who you can speak to.

For all I know, he's still in denial.

Right after he got out of jail on his Facebook,

he had the heading, "Darryl McCauley. I'm a very honest man.

I'm a very honest person."

They were ordered by the judge to pay restitution to Dane.

The possibility that Darryl McCauley

and Erika would be able to earn $12 million

to repay Dane was a fantasy.

Darryl is only paying back $50 a month

after he stole 12 million from Dane is sickening.

12 million and change.

To date,

what is the total amount of restitution

that's been paid by the defendant?

3,900, Your Honor.

His outstanding amount is $12,088,130.34.

I've never really looked at that or cared.

I can't say I expected anything different.

The why, it's part of the mystery.

He said that at the first

it was to cover some of his bills.

It got so out of hand, he just kept going.

He just would not say anything else.

And that's why it haunts me that maybe he did this for me.

I could pontificate the sociopath and psychopath,

impact disorders from the McCauley DNA and abuse.

How much was her detailing, "This is how we can do it."

We could what if this thing till the cows come home.

The only way I would ever know a version of it

is to be able to sit across from him and say, "Why?"

The court has a file cabinet.

They have a lot of sealed evidence.

There's certain things that I have never heard or seen

that would be astonishing to learn.

Darryl, shortly after you,

wrote an apology to you?

Mm-hmm.

Not to me!

He wrote an apology that I understood

he must have read in court.

Read it?

Oh, you have it?

Can I have a second?

Okay, let's go.

Yeah!

- Okay? - Okay!

Okay!

Oh, boy.

Oh, boy.

Ready?

Yeah, yeah.

- Oh, boy. - Okay.

All right.

Okay.

So Darryl wrote, "Thank you, Your Honor.

I would like to take this opportunity

to apologize to my brother, Dane,

for all of the hurt and anguish that I've caused him,

as well as the rest of our family.

I'm hopeful that someday my brother can forgive me

for my actions.

I feel that today is the beginning of the healing process.

It is clear with the benefit of hindsight

that I became intoxicated by the lifestyle

and large sums of money

that were generated by my brother's success

and wrongfully felt entitled to them.

I stand here feeling ashamed about what I have done

and will use my time spent in jail

to become the person that I was before losing my way.

I promise the court, my family,

and Dane that I will do everything in my power

to make things right.

Thank you, Your Honor."

I'd love to go talk to him about this letter.

Maybe even ask him if he would read the letter.

Court?

Mm?

This is the letter that Darryl read in court

when I walked out.

Oh, wow!

His, his plea to the judge, so to speak.

I walked out. I didn't wanna hear it.

Hmm.

I wanna believe it, but it does feel cold.

How do you feel?

I felt nothing reading that.

He had so much time to reach out to us and-

Right!

There are other ways to do this.

It sounds good, but it doesn't feel like real.

It feels something's empty or cold, or.

If he really, really was sorry and wanted to, you know-

Make amends! Like, why wouldn't he reach out?

I would love to sit with him

and just try to understand even just a piece.

Well, he's out there.

Where?

In this vast city that we call Beantown.

You should've done that.

Oh, remember that?

Whoo!

Oh, lordy.

All right.

Thank you.

Have you ever thought of

reaching out to Dane to apologize?

I've never thought about reaching out to Dane.

In my mind, he is the one who put his brother in prison.

If he really cared about his brother,

he would have talked to him.

He would have made him sit down

and talk to him about what happened,

about what is going on.

Did he do that? No!

He called the cops.

He sent them after his brother

and refused to talk to his brother.

Darryl tried several times to reach out to him.

Nothing!

So if he can't do that for his brother, why should I?

Darryl might not have told you this,

but Dane did try to reach out to him a bunch of times

and Darryl wasn't returning any of it.

The only thing that he did return was that voicemail

once you guys were on the trip,

and he never contacted Dane again.

Oh!

Yeah!

In fact,

Dane actually wanted to have the conversation with him

before it got that far,

but they found out the $3 million check.

Darryl wouldn't get back to him

even once you guys were back in Boston.

Wow.

Dane had no choice.

I hope this is gonna be part of that interview

because then I owe a huge apology to Dane.

And I never thought I'd say that.

I'm sorry!

If I had known that you tried to get in touch with him,

I would've made sure he did.

If Dane is interested in talking to me,

I would accept a phone call just based on that.

Dane, deep down,

I don't think he'll ever have full closure.

I didn't feel any closure after the trial.

I still don't.

I don't think I, I ever will.

Mm.

I really had a hard time accepting it for about a year.

I had to go to therapy, go on medication.

The only way I could really get past it is

just think, like, "My brother died."

Pretend that he doesn't exist anymore.

That's how I got past it.

Yeah.

There was a good part of him somewhere

that I saw and I grew up with.

It's a lot of mixed emotions.

We miss him.

You know, we really miss him.

This was March of '06.

My mom being ill.

I'd written a letter

as we were shooting the documentary series, "Tourgasm."

I'm good with titles.

He wrote back, "Dane, I'm very happy to tell you

that I was able to convince Mom

to share some of her memories of you

on a cassette recorder tonight.

It was nice that we were all able to be on the phone

to hear your good news.

Love, Darryl."

I love this Darryl. This Darryl, I love.

These are the moments that made me

wanna work with my brother for the rest of my life.

Like, five years later, the IRS called.

"Hey, good job. We're sending you a check."

And they sent me the entire amount of what I had paid ahead

in unpaid taxes.

I paid $6 million when I still had nothing.

I was like, "By the way, do I get the interest

since you guys have been holding my money now for five

to six years?"

And they didn't care for that.

And I bought that house that year.

He took me up there.

He opens the door.

He does a sweeping arm motion and he goes,

"Jokes! Jokes paid for all of this."

He's got a house you see in the movies.

You did it! You did it! You did it!

Still in it.

Sometimes I sit on that porch right where I sat with Darryl.

Sometimes I'll be like, "Man, you missed out."

I wake up every single day

the way I did when I first started standup comedy.

I'm enthusiastic, perpetually curious.

It's still based on that lonely kid in the playground.

Love "Jeopardy."

I can just watch it and get away from it all.

Dane Cook's half-brother

and business manager stole millions from the comic.

This crime of misappropriating bank funds.

Jeffrey? - What is embezzlement?

That's the word.

We gotta keep going.

We've only begun.

You know, he's a legend. Dane Cook, everybody!

Bank of America and I settled.

They made an offer

and I just said, "I'll take it. Let's go."

Is there still money of mine hidden out there today?

I do believe that there's money out there.

I believe there's people that know more.

It's something that Courtney

and I will talk about from time to time.

Like, "What else do you think we'll find out someday?"

My speculation is that Darryl's getting at it somehow

or it's waiting for him.

Who knows?

I wish there was a way to draw that out.

Go, "Hey, you're that guy from the news story.

You got any of that money? We can launder that in Bitcoin."

There was a million dollars

that was unaccounted for.

Whether it's been spent

or whether it's sitting under a potted plant somewhere,

it's still in the wind.

Dane,

knowing that Darryl's probably gonna be watching this,

is there anything you'd wanna say to him?

Darryl!

To the future.

♪ Hero ♪

♪ He'll find you ♪

♪ Taking ♪

♪ It all ♪

♪ Find me ♪

♪ In tragedy ♪

♪ Nothing ♪

♪ Crazy now ♪

♪ Down, down down ♪

♪ Take your word but you were ♪

When he was still being held at Middlesex County Jail,

I went to see the Celtics play.

They were in the finals.

I go to the Liberty Hotel. The manager greets me.

He said, "We would like to put you in the Ebersol Suite."

Drop my bags. I sit here. I turn on the TV.

"Welcome to the Ebersol Suite,

located in the heart of Downtown Boston,

with gorgeous, mesmerizing views of the Charles River,

of Fenway Park.

What a lot of people may not know as they're looking at this

is the Liberty Hotel was once!"

And then they explain it was a jail.

Look at this building. This was the clink.

This was the hoosegow.

I'm remembering somewhere around here

is Middlesex County Jail, and then realizing,

"Where is Darryl now?"

And I look across and I can see the red stripe

that used to go around that building.

And that building right there

is where Middlesex County Jail was, right there.

I'm staring from the most beautiful suite in the world

at the most tragic suite ever created

that was reminding me my hard work got me here,

and whatever work he considered hard work got him there.

It's the beginning of a new chapter right here.

We're sitting right here.

♪ Ah ♪

♪ But not there ♪