Funny Money: The Dane Cook Story

The list of celebrities caught breaking the law would require more pages than a vintage phone book. You less frequently hear about celebrities who were the victim of crimes, probably because they often prefer to take their losses and avoid the bad publicity. Dane Cook couldn’t afford to do that, because his embezzling former manager nearly cleaned him out entirely. Why did Cook trust him? Because Darryl McCauley was his half-brother. Consequently, McCauley’s betrayal was even more painful, as Cook admits in Brett Harvey’s very personal true crime documentary Funny Money: The Dane Cook Story, which premieres on VOD.

Cook starts the film jokingly advising viewers to always sign their own checks—but he is not entirely joking. You often hear rumors about athletes defrauded by their managers, but in Cook’s case, it is easy to understand why he trusted McCauley. Although technically half-brothers, their mother essentially raised them like full-blooded brothers. McCauley was also a former correctional officer, but Cook decided to hire him to handle his business affairs after his half-brother survived a particularly brutal prison attack.

If you are wondering how much money Cook had for McCauley to embezzle, Harvey rewinds to chronicle early Cook’s life and career. For some, Cook came out of nowhere, suddenly hosting SNL and starring in movies. However, he was one of the first stand-ups to successfully build and mobilize an online following. (He was using myspace at the time.)

Harvey’s coverage of the embezzlement is rock solid and airtight. He incorporates interviews with several law enforcement investigators from various government agencies. For the sake of closure and the truth, Cook offered to waive the court-ordered restitution for McCauley and his ex-wife, Erika (Montessi) McCauley, if they agreed to sit for interviews. She accepted the offer, but he did not. Frankly, Montessi-McCauley should be embarrassed by her appearances, but it could be healthy for her, because if she watches the film, it will rudely shake her out of her denial.

On the other hand, Cook’s stock should rise considerably with viewers. For starters, the way he rolled up his sleeves and got to work paying off his debts (in addition to the embezzlement, McCauley didn’t bother to pay Cook’s taxes for six years) is admirable. Nearly all Cook’s living family participated (including his two sisters), so a surprising intimate portrait of the comic emerges as a result. Clearly, Cook had a lot to process, but he appears to have successfully moved on with his life. Granted, he is a Red Sox fan, but we can probably forgive him for that.

Weirdly for a true crime-ish doc, Funny Money is often quite amusing, thanks to one-liners regularly tossed off by Cook and his friend, comedian Al Del Bene (they both also get credit for performing together for the troops in Iraq). Without question, Harvey’s film has far more substance than the typical celebrity bio. Recommended for fans of Cook and true crime, Funny Money: The Dane Cook Story releases this Tuesday (9/29) on VOD platforms.