By Dustin Rowles | Film | November 9, 2026
I’m not a fan of Dane Cook for myriad reasons: his comedy, his sense of humor, his personality, the movies he’s made, the jokes he’s stolen, the way he talks, and sure, the way he looks, too. But for a three or four-year stretch, he was one of the biggest comics in the world, and now, two decades after that stretch ended, he’s back with a documentary, Dane Cook: Funny Money. And it’s true crime.
In 2008, Cook discovered that his half-brother, Darryl McCauley, had been siphoning money from him for four years. By the time Cook caught on, most of the $12 million he’d amassed over his career had vanished. It is easily the most interesting thing about Dane Cook. It is also not that interesting, at least as true-crime documentaries go.
True-crime docs, especially the Netflix variety, traffic in complicated narratives, malicious crimes, dead bodies, and jaw-dropping twists. Funny Money is about the time Dane Cook’s half-brother stole his money. Darryl didn’t hatch some insane or brilliant scheme. He managed Dane’s finances. He wrote himself checks from Dane’s account. He didn’t tell Dane, and Dane never looked, because he trusted his half-brother.
When Cook moved to Los Angeles, however, he hired an accounting firm to manage his money. The firm requested Cook’s financial records from Darryl, and Darryl stalled for weeks, then months, before writing himself a $3 million check and bolting. Cook called the cops. Darryl was arrested. Cook recovered several million dollars Darryl had stashed around his condo (in plants, in mattresses, in spaghetti sauce), and eventually paid off the $6 million in back taxes Darryl had never sent to the IRS on his behalf, and the brothers went their separate ways (Darryl’s way led to prison for three years). They never spoke again.
Beyond the obligatory Rise of Dane Cook first act, that’s about all there is to the story, save for one other player: Darryl’s now ex-wife, Erica, who also went to prison for conspiring with Darryl. Together, they burned through millions: $5 million in credit card charges, $500,000 in jewelry, and another $400,000 to bankroll Erica’s new business. She appears in the documentary, too, mostly to insist, with a straight face, that she had no idea Darryl was stealing. She just figured he had a lot of money, and she was gullible.
But not as gullible as anyone who believes her. (She agreed to participate only after Cook waived her restitution, which she was probably chipping away at in $50 monthly installments, like Darryl.)
It’s a two-hour documentary that could have been told in half an hour. I’m sorry Dane Cook lost his fortune. I’m happy he climbed out of the hole after recovering most of it. But the story of Dane Cook’s brother does not merit two hours of Netflix real estate, and it’s only mildly interesting because it involves someone who used to be famous.
(And yes, Dane Cook’s 28-year-old wife makes a few appearances for no real reason other that she lives in the same house where much of the doc is filmed).