Darryl McCauley, Dane Cook's half-brother, has made headlines recently, as the comedian's new documentary Funny Money explores a serious financial betrayal. McCauley served as Cook's business manager for several years before being charged with embezzling at least twelve million dollars from him in 2008.
As per a report shared by Entertainment Weekly, Darryl McCauley was present from the very beginning of Cook's rise to fame, which kicked off in 1998 with Comedy Central's Premium Blend. That eventually led to HBO specials, Saturday Night Live hosting appearances and film roles with Kevin Costner and Jessica Simpson.
"He would handle every aspect of every penny that came in," the documentary reveals.
What Cook didn't know was that McCauley had been quietly siphoning money from his personal accounts the entire time. McCauley pleaded guilty and served six years in jail before vanishing altogether.
In the trailer for Funny Money, Cook, who is known for his role in Good Luck Chuck, describes his older half-brother, a former corrections officer, as "a person that spent so much time pretending to be something he wasn't."
"I was starting to feel something that I couldn't really identify," Cook admits.
"Was he hiding it in different places, stockpiling this money?" he added.
Darryl McCauley hid stolen cash inside jars of spaghetti sauce:

Cook's suspicions turned out to be well founded. Darryl McCauley had been stashing bricks of cash in multiple hiding places, one of which included jars of spaghetti sauce, after first wrapping the cash in plastic.
An investigation determined that Darryl McCauley had embezzled at least twelve million dollars from Cook. That being said, Cook believes the actual figure could be even higher.
"I do believe that there's money out there. I believe there's people that know more," he says.
As the walls closed in, Darryl McCauley reportedly "disassociated" from the reality of the situation. In the trailer for Funny Money, Cook plays a voicemail from his brother, in which Darryl McCauley can be heard saying he heard
"the FBI is involved with something. Dane, what happened? What have you done?"
Martha Coakley called out Darryl McCauley for abusing Dane Cook's trust:
As per a report shared by CNN back in December 2010, Darryl McCauley and his wife Erika were ordered to repay Cook the twelve million dollars they admitted to stealing while managing his business, a spokesman for the Massachusetts Attorney General confirmed.
Darryl McCauley pleaded guilty to larceny, embezzlement and forgery charges. His wife Erika pleaded guilty to larceny charges. Attorney General Martha Coakley had something to say after his sentencing.
"For several years, Mr. McCauley abused his position as a family member to gain Mr. Cook's trust, and stole millions of dollars for his own personal gain," said Coakley.
Dane Cook watched Darryl McCauley's embezzlement case turn into a Jeopardy question:

As per a report shared by People back in 2018, Dane Cook was forced to relive an embarrassing family incident while watching Jeopardy. Cook posted a hilarious response on Twitter after Darryl McCauley's embezzlement case was used as the basis for a question on the popular game show.
"I love Jeopardy, I can just watch it and get away from it all," Cook jokes.
The clip then cuts to the television show, where the following answer pops up on screen,
"Dane Cook's half-brother and business manager stole millions from the comic, this crime of misappropriating bank funds."
A contestant then correctly responded,
"What is embezzlement."
Dane Cook is reportedly stepping into the horror world:

Dane Cook also made headlines recently, as Jeff Barker, a screenwriter and the father of Obsession director Curry Barker, tapped him to star in a psychological horror short film. The project, titled Medium Rare, also stars Lesley Ann Warren.
As per a report shared by The Hollywood Reporter, the story centers on a man who found himself trapped inside a bar as his grip on reality slowly deteriorated. Filming is expected to kick off in Los Angeles.
Barker isn't new to the genre. He previously worked as a script consultant on Obsession, a breakout horror hit that his twenty-six-year-old son wrote and directed on a budget of seven hundred and fifty thousand dollars. Barker also runs The Screenplay Lab, a podcast dedicated to the art of screenwriting.
He spoke about the project in a statement.
"Medium Rare is a short story I wrote eight years ago. I'm honored by the team of people helping me bring this project to life," Barker said.
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