Dane Cook Reveals How Brother’s Betrayal Upended His Career

Dane Cook had big plans for his comedy career until his half-brother, Darryl McCauley, embezzled at least $12 million from him.

“I was always a guy that made a plan and worked and worked toward the goal,” he told Obsessed: The Podcast. “In 2008, what I wanted my career to be was basically where somebody like Kevin Hart is now. I was like, ‘I’m coming down the other side. I’ve put this money aside. Now I’ve got some nest egg for me, but I’ve got enough money that I can make things, and I can help other people make stuff.’”

But McCauley, who served as Cook’s business manager, sent the comedian’s future careening off course. Cook had wanted to direct and produce films with his production company, Great Dane Enterprises, which he planned to expand. He was at the height of his stand-up success and was starting to understand the ins and outs of the business.

The brothers were close until Cook discovered that McCauley had stolen millions of dollars from him between 2004 and 2008. In 2010, McCauley and his wife, Erika, pleaded guilty to larceny, embezzlement, and forgery. Erika was sentenced to two to three years in prison; McCauley was sentenced to six years and ordered to pay Cook restitution.

After serving his sentence, he disappeared—without returning the money. Cook explores all of this and more in his documentary, Funny Money: The Dane Cook Story, streaming on Apple TV and all VOD platforms starting Tuesday, Sept. 29.

“If this never happened, I would like to think we’d probably be sitting here talking about films that I’m making with my company, whether I’m in them or directing them, or just helping other young talent find their way,” Cook said. “And by the way, my whole thing was protecting other people from the piranhas of the industry. And there I was sitting next to the devil that was my brother.”

He recognizes the irony in his situation. Before his brother’s betrayal, Cook aimed to use his success to help newer comedians. He wanted to be a reliable, moral presence in an often corrupt industry.

“All I wanted to do was have that next phase of my career be like, ‘Let me help other people, and hopefully I can be the person that’s like, ‘I don’t need or want anything from you. I just want you to have your integrity and make it the way I made it on my own,’” he explained.

An early career setback came when Cook “blew” his audition for Saturday Night Live after the show scouted him at comedy clubs. Adam Sandler had just left, and the show needed someone who was “affable and excitable” to replace him. Cook made it to Rockefeller Plaza, but he didn’t make it inside the building.

“One of the worst panic attacks of my life was sitting on a bench at Rockefeller Plaza,” he said. “I mean, I’m crying; I can’t breathe. I’m sort of catatonic on a bench. I’m bawling, and I’m gripping the bench, and I find a payphone, and I call my manager. I go, ‘I can’t do it. I can’t go in.’”

Cook said he wasn’t prepared for the pressure of SNL, where he would have to fight for his ideas in a high-stakes environment. He described himself as “beta” and said that, despite his “broad shoulders,” he was “very scared.” Jimmy Fallon ended up filling Sandler’s void.

“Would I have gotten it? I don’t know,” he said. “Jimmy’s a very talented guy. I think that Jimmy was also sort of at a precipice. But there was ‘shoulda, coulda, woulda’ for a few years where it was really nothing happening, like, man, I blew it. I blew my dream.”

Cook is doing better now. He’s trying to reach a point where he views his brother’s deception as “a blip on the map.” He’s spent a decade learning, doing therapy, and rebuilding his life and career “brick by brick.”

“I feel like I’m putting out some of my best work,” he said. “And I can’t wait for my next comedy special to be able to show people where I’m at.”