Comedian Reveals Shocking Details About Brother’s $12M Theft

Stand-up comedian Dane Cook’s mother warned him about his half-brother, Darryl McCauley, at the end of her life. Two years later, McCauley was arrested for embezzling at least $12 million from Cook over four years.

“My mom said on her deathbed, ‘Your brother... you gotta look out for him,’” Cook, 54, told Obsessed: The Podcast. “There was a long, wild conversation with my mom that ended with her trying to warn me. I didn’t want to accept that, but it was the beginning of me starting to look at things differently. It was the last gift my mom gave me before she passed away. And lo and behold, I finally uncovered a really terrible truth in my family.”

McCauley, 61, was Cook’s business manager during the height of his stand-up stardom. The brothers grew up loving comedy and shared a close relationship—until Cook discovered that McCauley had stolen millions of dollars from him between 2004 and 2008, hiding plastic-wrapped cash bricks in frozen containers of pasta sauce and empty boxes of bagel bites.

Cook explores the fallout in his documentary Funny Money: The Dane Cook Story, streaming on Apple TV and all VOD platforms starting Tuesday, Sept. 29.

McCauley and his wife, Erika, pleaded guilty to larceny, embezzlement, and forgery in 2010. Erika was sentenced to two to three years in prison; McCauley was sentenced to six. McCauley was also ordered to pay restitution, but instead of returning the money to Cook after his prison term, McCauley disappeared.

While McCauley refused to take part in the documentary, Erika agreed to sit for an interview, during which she largely maintained her innocence. But to Cook, her act wasn’t convincing; he had poured over evidence that made it clear “she was a willing participant,” he said.

He explained that Erika seemed to have been “gamifying certain things” based on “certain letters and correspondence that I found years later.” He also said email threads indicated that Daryl and Erica had done “a lot of game planning and prepping” during their scheme.

Mass quantities of money would vanish from Cook’s bank account while McCauley was his business manager, sometimes up to $100,000 at a time, culminating in Cook receiving an alarmed voicemail message from McCauley claiming the FBI was after him.

Though Cook had already begun grappling with the idea of his brother as “a thief, nefarious on the run,” before the voicemail, he was “still holding on to hope that maybe my brother got hit on the head. Maybe there’s an explanation,” he said.

“And when I played that answering machine message, two things hit me immediately,” Cook continued. “The first time I heard it, it was, ‘He’s faking it. This is a terrible, terrible performance.’”

The second thing he realized was, “I needed to keep this. I need to record this.”

Though McCauley has still repaid Cook the money he stole, Cook offered to alleviate the massive debt under one simple condition.

“I wanted to sit with him,” Cook said. “That was the one thing I told the director. I said, ‘I want to sit with him. I want to sit opposite him.’ And there was a correspondence, not between him and me directly, but through our legal team. I’ll just leave it at: the plot thickens. I think that the bagel bite/sauce era is over.”

When Cook heard McCauley’s panicked voicemail message years later while filming the documentary, he felt something unexpected.

“I missed my brother,” he said. “I missed him. I missed the guy before that call. It was weird because I didn’t think I missed him anymore. I thought I’d got past it, and it was a season of my life. And I’ve grown from it; I’m better from it. But man, I forgot that I still missed having a brother.”