A new documentary, 'Funny Money: The Dane Cook Story,' examines the comedian's discovery that his half-brother embezzled millions from him.
Key facts
- •Darryl McCauley was ordered to pay $12 million in restitution in 2010.
- •The embezzlement was discovered by Dane Cook in 2008.
- •Darryl McCauley previously worked as a corrections officer before managing his brother's finances.
- •The documentary 'Funny Money: The Dane Cook Story' is scheduled for release on September 29.
- •Cook states in the film that he believes some of the stolen money remains unaccounted for.
Comedian Dane Cook is the subject of a new documentary, 'Funny Money: The Dane Cook Story,' which details the betrayal he faced when his half-brother and business manager, Darryl McCauley, embezzled $12 million from him. The film explores the financial theft that came to light in 2008 and the subsequent legal fallout.
Legal Consequences and Disappearance
In 2010, Darryl McCauley and his wife, Erika McCauley, pleaded guilty to charges related to the theft. Darryl was sentenced to six years in prison for larceny, forgery, and embezzlement, while Erika received a two-to-three-year sentence for larceny. Following his release from prison, Darryl McCauley disappeared.
The Embezzlement Scheme
McCauley served as Cook’s business manager while the comedian rose to prominence in the early 2000s. The documentary trailer reveals that McCauley systematically withdrew large sums from Cook’s accounts, including individual transactions of $20,000, $50,000, and $100,000. Cook alleges that his brother hid the stolen cash in various locations, including inside spaghetti sauce jars.
Timeline
- 2008Dane Cook discovered that his half-brother had been stealing money from him.
- 2010Darryl and Erika McCauley were sentenced to prison after pleading guilty to embezzlement and larceny.
- Sept. 29The documentary 'Funny Money: The Dane Cook Story' is scheduled to be released.
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This article was independently rewritten by ManyPress editorial AI from reporting originally published by Rolling Stone.

