Dane Cook looking mad on the set of The Tonight Show


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  • What Happened Between Dane Cook And His Half-Brother?
  • What Is The Status Of Dane Cook’s Relationship With His Brother Today?

At the height of Dane Cook’s career, there was no doubt that he was one of the most successful comedians in the world. Beloved by his troves of devoted fans, it briefly seemed like he could do no wrong as evidenced by the fact that his career survived after he skipped his SNL audition.


Unfortunately, there is a reason why the saying “what goes up, must come down” is so widely known. After all, Cook was on top of the world when his comedy career suddenly took a dive among accusations of plagiarism.

Related: What Happened Between Dane Cook And Louis C.K.?

If it wasn’t bad enough that Cook’s career hit the skids, Cook’s personal life has had a lot of ups and downs over the years.

Tragically for Cook, at one point he was forced to learn that he couldn’t even trust his family. The reason for that is Cook’s extremely complicated relationship with his half-brother, Darryl McCauley.


What Happened Between Dane Cook And His Half-Brother?

When Dane Cook was growing up in Massachusetts, he had five sisters and an older half-brother on his mom’s side. While talking about his half-brother, Darryl McCauley, Cook has described him as his first best friend.

Related: This Is The Worst Dane Cook Movie, According To Fans

To Cook’s eternal credit, he appears to be a loyal person. After all, once he made it big, he convinced his half-brother who was working as a prison guard to quit and come work for him. Since Cook trusted McCauley, he made the mistake of putting his half-brother in charge of his money.

After McCauley took control of his Cook’s money in the early-’90s, he remained in that role until 1998. Then, everything changed because as Cook explained during an appearance on the Your Mom’s House podcast, he decided to buy a home in California.

Since Cook was living in a different state, he sought out a new business manager. Still loyal to McCauley, he told his half-brother that he was going to employ him in a new role, possibly in fulfillment.

As Cook explained during the aforementioned podcast interview, his new business manager couldn’t get any information out of McCauley. The reason for that is McCauley had been embezzling Cook’s money for years and sending the famous comedian fake documents he made on his computer.

According to Cook, he woke up one morning and had the epiphany that his brother had been stealing from him. After getting help to investigate, Cook contacted the Attorneys General’s office in Massachusetts to report his brother.

Ultimately, McCauley pleaded guilty to larceny, embezzlement, and forgery charges. Additionally, Cook’s sister-in-law Erika McCauley turned out to be in on it which resulted in her pleading guilty to larceny charges.

After the trial, Cook’s brother was sent to prison for five or six years and his sister-in-law was sentenced to three years. McCauley was also ordered to pay Cook back $12 million.

Unfortunately for Cook, there was another wrinkle to the story. Since McCauley didn’t pay his brother’s taxes, Dane had to pay the government money he thought they got years earlier. Since Cook’s taxes were very late, he also was forced to pay fines.

On the bright side, the government refunded him the cost of the fines after McCauley pleaded guilty.

Finally, it is worth noting that there is a stunning twist to the story. According to Cook, McCauley was sent to the same prison where he used to work as a guard.

What Is The Status Of Dane Cook’s Relationship With His Brother Today?

Sometimes in life, people think that being related to someone by blood means that you always have to put up with them. In reality, however, nobody has to allow someone toxic to be a part of their life even if they are “family”.

Related: The Top 10 Most Intense Celebrity Sibling Rivalries

After what Dane Cook’s half-brother did to him, it should go without saying that the famous comedian doesn’t owe Darryl McCauley anything. That said, if Cook wanted to reconnect with his half-brother, it is possible now.

Since Cook’s half-brother McCauley was sentenced to five or six years in prison in 2010, he clearly was released several years ago. As a result, Cook and McCauley could have forged a new relationship by now if they chose to.

Unsurprisingly, there is absolutely no evidence that Cook and McCauley have reconnected. While it is important to note that Cook hasn’t explicitly stated he currently doesn’t have a relationship with McCauley, it really seems like that should go without saying.

Since 2017, Cook has controversially been involved with a much younger woman named Kelsi Taylor. In 2022, Cook and Taylor got engaged after he popped the question. As a result of everything that has gone on, it seems extremely likely that McCauley shouldn’t wait by his mailbox for an invitation to Cook’s big day.

Based on everything that is known about Cook and McCauley, two things connect them today. On top of being blood-related, McCauley still owes his famous brother millions of dollars.

Unfortunately for Cook, it seems all but certain that he will never see much money from his brother. Considering that McCauley doesn’t have access to that kind of money, he only has to pay a portion of the cash he makes and that’s assuming Darryl gets a job and follows the rules.

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