Dane Cook’s Brother Darryl Stole Millions from Him, Hid Cash in Spaghetti Sauce and Disappeared (Exclusive)
Dane Cook’s Brother Darryl Stole Millions from Him, Hid Cash in Spaghetti Sauce and Disappeared (Exclusive)
Rachel RaposasWed, August 19, 2026 at 3:00 PM UTC
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Dane Cook in ‘Funny Money: The Dane Cook Story’Credit: courtesy Upstream Flix -
Dane Cook’s new documentary Funny Money: The Dane Cook Story explores the dark side of his rise to fame
Dane’s brother Darryl managed his finances and subsequently stole millions from the comedian
The documentary will be available to stream on Sept. 29
Dane Cook is shedding light on the dark side of his fame.
Funny Money: The Dane Cook Story, an upcoming documentary directed by Brett Harvey, details the comedian’s meteoric rise “and his crash at the hands of the person he trusted most,” according to a synopsis of the film. Set to debut on Sept. 29, Funny Money goes behind the scenes of Cook’s career and explores the key role played by his half-brother Darryl McCauley — who ultimately stole millions from him.
In the trailer for Funny Money, which PEOPLE can exclusively reveal, the tense tale kicks off with audio of a mysterious phone call from McCauley.
“Dane, it’s your brother,” McCauley can be heard saying. He adds: “The FBI is involved with something? Dane, what happened? What have you done?”
The trailer then cuts to grainy family videos of Cook and McCauley. “A person that spent so much time pretending to be something he wasn’t,” Cook, 54, says in a voiceover, referring to McCauley. “From the moment he left that bank, my brother disappeared.”
Dane Cooke in ‘Funny Money: The Dane Cook Story’Credit: courtesy Upstream Flix
The two brothers had a shared interest in stand-up comedy, Cook reveals. As Cook successfully built his career in the industry, McCauley was always pictured right beside him, supporting his brother.
“Once [Cook] started going platinum, everything changed,” a commenter says. Another adds, “He was like a rock star.”
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McCauley, who was Cook’s business manager from the ’90s through 2008, handled every penny of Cook’s wealth. But paper trails showed he was withdrawing huge amounts — up to $100,000 at a time — from his brother’s account.
Cook says he began to feel “something I couldn’t identify,” and questioned where all this missing money was going.
‘Funny Money: The Dane Cook Story’Credit: courtesy Upstream Flix
The trailer then cuts to a wall safe, stuffed to the brim with cash. And that wasn’t McCauley’s only hiding spot: “There were bricks of hundreds in all the spaghetti sauce,” a voiceover says.
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“I do believe there’s money out there. I believe there’s people that know more,” Dane asks at the end of the trailer. “Where is he? What has he done? How does this end?”
McCauley, 61, a former corrections officer, was ultimately arrested in 2008 and charged with stealing $12 million from Cook while acting as his business manager. He pleaded guilty to larceny, embezzlement and forgery in 2010 and was sentenced to five to six years in prison. He was also ordered to repay the $12 million to Cook. His wife Erika was sentenced to two and a half years in connection to McCauley’s crimes.
Funny Money: The Dane Cook Story is available on VOD Sept. 29.
on People
Source: “AOL Entertainment”
