‘Funny Money’ Doc Became ‘Speed Dating Therapy’ For Dane Cook As Comedian Confronted His Brother’s $12 Million Theft

Dane Cook holding the slate for his biographical documentary ‘Funny Money.’

Famous Red Car Pictures Inc.

By the late 2000s, Dane Cook was on top of the world.

His meteoric rise as a comedian/actor double threat made him one of the hottest, most successful names in the world of entertainment. His second comedy album (Retaliation) went platinum, he sold out Madison Square Garden (only the second standup to do so), and starred in a string of studio films alongside Dax Shepard, Steve Carrell, Kevin Costner, and Jessica Alba.

With his half-brother Darryl McCauley at his side as trusted business manager, it seemed as though nothing could stop his ascent. But never in a million years—or 12 million, to be more exact—would Cook have imagined the man he had implicitly trusted to handle his finances would end up betraying him by stealing nearly ever cent he had earned. It was only when the comedian tried to buy a house in Los Angeles that he learned of his brother’s treachery to the tune of $12 million.

But that’s only the beginning of a sad and bizarre tale of bicoastal thievery that might have leapt off the pages of an Elmore Leonard novel. The whole affair takes center stage in the new documentary, Funny Money (now on VOD and digital).

“It is funny,” Cook summarized of the ordeal over Zoom. “Funny and weird.”

The comedian, 54, felt he was ready to share his experience with the world after recounting a fraction of it on a 2019 episode of Tom Segura’s podcast, Your Mom’s House. “I left that podcast and was like, ‘Man, I really overshared, but think I’m starting to feel like confident enough to talk about this very humiliating, heartbreaking, financially-breaking betrayal,’” he said.

Not long after, producer Rocky Mudaliar introduced him to Brett Harvey, whose 2019 documentary Inmate #1 chronicled the rise of Danny Trejo from prison inmate to Hollywood icon.

“I met Brett, and said, ‘I’m ready to tell my story, but what I need to know is are you ready to put a camera on me?’” Cook recalled of his initial dinner meeting with Harvey. “’Because I’m going to give you everything in here. I don’t even know what all of it is, but if you ask the right questions, I think you’re gonna get some pretty interesting answers.’ What I didn’t realize when I sat [down to be interviewed], was that Brett was not only ready, but he came in with a dossier of information I didn’t know. I remember leaving the chair many times and going, ‘Whoa, this is really all out there. This is a little scary. What happened was scary, but the vulnerability and story itself are intimidating even me.’”

Among the dossier materials was the forensics audit that Cook had sanctioned to, in his own words, “un-f*** the situation.” But his numb state of shock at the time prevented him from paying attention to the minutiae of Darryl’s misdeeds. “I am absolutely hull-crushed, depth level busted-up and don’t know how to move in the world,” he recalled. “I was there, but I wasn’t.”

Who could blame the guy?

He’d been stabbed in the back by one of his closest confidants and, to add insult to injury, now owed millions in back taxes and penalties to the IRS.

“Brett had all of that [information],” Cook explained. “And then here I am, years later, and he’s re-presenting this binder to me. But this time, I’m really seeing it. He had everything. Every number, every email; things I didn’t think he’d ever have access to. When he was putting those things in front of me, you’re getting a genuine reaction of, ‘I’m heartbroken again,’ but also finding humor in something so dark and terrible as what that was.”

Part biography and part true crime yarn, Funny Money was not envisioned by Harvey to be a sugar-coated puff piece. His desire to get at the objective truth made Cook feel like he “was crossing one of those rickety old rope bridges where you’re like, ‘All these boards are not solid.’”

As a result, the grueling 10-to-15-hour interview sessions became a kind of “speed dating therapy” that allowed Cook to start wrapping his head around the inconceivable familial deception. The goal is for people to walk away from the documentary feeling entertained and inspired.

“I really think it’s a story about dignity,” Cook said. “There’s no shame in showing your weakest moment in life. In fact, it makes you more powerful than ever. I hope it allows you to watch a moment like mine, and say, ‘You know? It’s not a bad idea to find a little bit of humor in life anywhere and everywhere you can.’”

Aside from Cook, the documentary also features interviews with family members, childhood friends, financial advisors, and law enforcement personnel who try to understand why Darryl did what he did. Perhaps the most fascinating personality of them all is Darryl’s ex-wife, Erika, who continues to claim she had no knowledge of the embezzlement scheme, which culminated in the discovery of cash hidden behind bathroom walls and submerged in jars of pasta sauce.

“I’ve seen the emails and know how much more she was steeped and involved,” asserted Cook. I’m watching somebody very keen, who’s very good at moving in the world to where shadows are of her advantage. I’m not a person that’s ever had hate or anger, but it’s bringing up the part of her that I detested and was familiar with. But as a creative person, [I think] she’s what you or what I would call ‘good documentary [fodder].’ I’m mesmerized by what she’s bringing to my story, and dare I say I’m thankful that she’s in it because I love true crime. I love documentaries. She’s giving documentary.”

Erika agreed to be interviewed in exchange for Cook forgiving her court-mandated restitution after she pleaded guilty and spent three years in prison. Darryl, who served a six-year sentence, declined a similar offer that would have nullified his debt if he simply sat down for an on-camera conversation with his brother.

“I can’t speak for him, but I’d like to think that part of it is he probably just can’t face the fact that I would say, ‘What you did to me is nothing compared to what you put your son and our little sister through,’” mused Cook. “He knows who I am. He knows that I would ask those questions, especially if you put a camera on me. He knows I’m not gonna [hold back and want] to give give everything I have to try to be as real and reactive and present as possible.”

What’s truly incredible is the fact that Cook recouped his money and paid off the IRS in short order by renting out arenas for comedy shows with his own money. Along with the desire to be financially stable again, he also wanted to walk into the courtroom and let Darryl know he no longer had anything over him.

Still, a year of back-to-back standup gigs took its toll on Cook’s mental health.

“I was like, ‘Not only am I not healthy because of this thing with my brother, [but] I have yet to grieve my mom and dad. I am on a a crash course to some form of breakdown,” he confessed. “So I started immediately getting what I would consider the right help [to get] the pinprick of release I needed … But I didn’t even understand what would need to transpire in the years ahead for me to even get to a place here where we’re talking about it in a somewhat lighthearted manner.”

Even with a two-hour documentary devoted to the subject, “there’s more to the story,” Cook teased. “I can’t say too much now, but I’ve been approached by certain people. Who knows? Maybe we’ll chat about this later when there’s more to share.”

Among those people is John Mulaney, who reached out to his fellow standup via proxy to ask about turning the nightmarish experience into a one-man show. Mulaney, of course, achieved great success on Broadway with his and Nick Kroll’s Oh, Hello.

“I don’t know if he still feels that, but there might be the possibility to partner up with the right people who see value in it,” concluded Cook. “I’ve always wanted to do Broadway. It’s been a dream of mine. There’s many tentacles and [bits of] story we didn’t get into. We had to make it a toe-tapper and something that really moved. But there’s more to tell and more to share. I think there’s a way to do it that could possibly be in that one-man show element. But I would have to write one musical number for it because I love to sing.”

Funny Money is now available on VOD and digital platforms.