Trailer for the revealing new documentary is now streaming on YouTube ahead of its September 29 digital release.
Dane Cook’s meteoric rise to comedy superstardom — and the devastating betrayal that unfolded behind the scenes — takes center stage in the upcoming documentary Funny Money: The Dane Cook Story. The official trailer is now streaming on YouTube, offering audiences a first look at the deeply personal story behind one of stand-up comedy’s biggest success stories.
At the height of his career, Cook seemingly had everything. He was selling out arenas, releasing blockbuster comedy albums and specials, and becoming one of the most recognizable comedians of his generation. But while his career was reaching unprecedented heights, a shocking betrayal was taking place much closer to home.
Funny Money: The Dane Cook Story explores Cook’s complicated relationship with his half-brother, Darryl McCauley, who worked alongside the comedian throughout his rise to fame before ultimately stealing millions of dollars from him.
The documentary traces the brothers’ relationship back to their shared interest in stand-up comedy. As Cook began building his career, McCauley was frequently by his side, becoming a trusted figure within his brother’s growing business operation. What initially appeared to be an unbreakable family partnership eventually became one of the most painful chapters of Cook’s life.
Through Cook’s perspective, Funny Money examines how the betrayal unfolded, the emotional and financial damage it caused, and the comedian’s fight to regain control of his career, finances and personal life after discovering that someone he trusted most had taken advantage of him.
Beyond the millions of dollars involved, the documentary offers a more intimate examination of the cost of success, the dangers of mixing family and business, and what happens when loyalty becomes exploitation.
Cook’s story also provides a rare look behind the curtain of his extraordinary rise in stand-up. During his peak, he became a defining figure of 2000s comedy, translating an enormous fanbase into sold-out arenas and mainstream celebrity at a level few stand-up comedians had achieved.
Now, Funny Money: The Dane Cook Story revisits that era from a dramatically different perspective, revealing the personal turmoil unfolding while Cook was publicly experiencing the greatest success of his career.
The newly released trailer previews a documentary centered not simply on financial crime, but on trust, family, survival and rebuilding after betrayal.
The trailer for Funny Money: The Dane Cook Story is streaming now on YouTube.
Funny Money: The Dane Cook Story will be released September 29, 2026, and will be available across Apple TV, Google, Fandango at Home, iNDEMAND, DISH Network, Sling TV and DIRECTV.
