Dane Cook’s Brother Stole $12 Million, Went to Prison, Then Disappeared

In 2010, Dane Cook ‘s brother was ordered to pay the comedian $12 million after he and his wife pleaded guilty to embezzling the money.

Darryl McCauley was sentenced to six years in prison on charges including larceny, forgery, and embezzlement; Erika McCauley was sentenced to two to three years in prison on charges including two counts of larceny.

After serving his sentence and being released from behind bars, McCauley disappeared.

“Where is he? What has he done? How does this end?” Cook narrates at the beginning of his new documentary, Funny Money: The Dane Cook Story , which dives into the betrayal that consumed the comedian in 2008, when he discovered his half-brother and business had been stealing millions behind the scenes.

In the trailer for the film, Cook describes how he and McCauley both aspired to grace the stage as stand-up comics. Cook would go on to become one of the most popular comedians of the early 2000s, while McCauley took on a job as a corrections officer and would later handle his brother’s finances directly. Looking back at their time together, Cook observes how McCauley was “a person who spent so much time pretending to be something he wasn’t.”

As Cook’s rise as one of the highest-paid comedians continued, the clip depicts McCauley withdrawing $20,000, $50,000 and even $100,000 from Cook’s accounts. “I was starting to feel something that I couldn’t really identify,” Cook says. “Was he hiding it in different places, stockpiling this money?”