Dane Cook Opens Up About Half-Brother's $12 Million Theft in New Documentary

Dane Cook, once one of the most successful stand-up comedians of his generation, is revisiting a painful chapter of his life in a new documentary. "Funny Money: The Dane Cook Story" examines how his half-brother, who managed his finances, stole more than $12 million from him over several years.

The theft led to Darryl McCauley being sentenced in 2010 to more than five years in prison on larceny charges. The documentary traces the brothers' childhood and features interviews with friends and family who knew them both, as Cook attempts to understand why his brother committed the crime.

Cook said he had long been drawn to true crime stories, and when the betrayal unfolded, he found himself both shocked and fascinated by the mechanics of it.

"I was really fascinated at the idea that you could be so close to somebody or people, and they were nefarious," Cook said. "All is not what it seems. And so, to have been embroiled in my own version of that."

He added that after the initial shock, he wanted to find a way to share his experience. "Once I took a deep breath, it was like, I want to someday, I don't know when, figure out a way to share all of this because I know it's entertaining because my life has been entertaining."

Cook gave writer-director Brett Harvey full control over the narrative, declining to see edits or other interviews. He said he sat for what felt like 15 hours a day over months, answering questions.

"I said listen, I don't want to see the edit. I don't want to know about other interviews. I'm not gonna look at clips, excerpts. I will sit in the chair and if you ask me the right questions, I'm going to give you everything I have," Cook said.

The process, he said, left him in a constant state of disarray as he relived and learned about events simultaneously. "But I'm also so far along in my healing and introspection that it feels so good to sort of say it, to really realize it and say it."

McCauley is now divorced and out of prison. Cook said he does not know whether his brother will watch the documentary.

"I used to say Darryl, you know, rewrote my past," Cook said. "Because I would look at pictures or video and say was he who was he then? Was he already on the take or was he -- how much did he love me there? Was he really protecting me there?"

Cook said he remains close to McCauley's son, his nephew. "There's a lot of my brother in him, same big blue eyes, same laugh."

One of the film's most striking elements involves Boston state troopers and investigators finding money in unusual places at McCauley's second home in Maine, including in the dirt of plants and inside pasta sauce jars in the freezer.

Cook recalled troopers calling him with the news. "In that thick Boston accent, I'd hear a state trooper say, 'You're going to be real happy, kid. Kid, we got 800 grand on a table. What's your email? We'll send it over.'"

He said the money was returned to him, allowing him to pay his mortgage and keep the house he nearly lost. "These are the moments where I said, I hope I can tell this story someday because it's so interesting and I can't believe this happened to me."