Dane Cook has had a long and interesting career as a comedian. He's sparked plenty of laughs, but also some controversy. Though comedians like Larry David got their start by faking illnesses and making connections, Dane's path was a little different. He failed a few times, including being booed off a stage, along with other comedians, before he succeeded, and once he was in the headlines, he stayed there.

Related: Why Did Dane Cook's Career Take A Dive In Recent Years?

Unlike Ricky Gervais, who always seems to get away with off-color jokes, Dane has seen some pushback from fans over jokes they thought went too far. But he also feuded with other comedians. For example, Joe Rogen accused Dane of ripping off some of his material. That seems to be just the beginning of Dane's stint in the public eye. He also made headlines years ago for landing his brother in jail. What happened, and what caused Dane to turn against family? Let's find out!

Updated on October 26, 2021, by Michael Chaar: Dane Cook dominated the comedy scene in the mid-2000s, earning himself millions upon millions of dollars. Well, after recruiting his half-brother, Darryl McCauley to work as his business manager, it was revealed that he couldn't be trusted. Between 2004 and 2008, McCauley and his wife managed to embezzle tens of millions from Dane. From forging checks, opening up businesses, all the way to purchasing properties, Darryl McCauley really screwed Dane Cook over. A judge ordered Darryl to serve 5-6 years behind bars, all while requiring McCauley and his wife to return the cash to the tune of $12 million, and rightfully so. While Dane and Darryl shared a bond prior to the scandal, the two are no longer on speaking terms.

Dane's Brother Was His Business Manager

Dane Cook reigned throughout the 90s and early 2000s, earning gigs across the globe, landing special after special, and even going as far as selling out Madison Square Garden. It was evident that Dane was doing very well for himself, despite it taking a bit of time to reach that level of fame and success.

From the 1990s to 2008, Dane Cook's half-brother was his business manager. Darryl McCauley made a staggering $12,500 per month while working in the role, and as fans on Reddit discussed, that should have been enough to carry him through life well enough. At least, that's what the average office worker would assume. Later, it turned out that Darryl had a side gig he wasn't about to reveal to anyone but his wife (though she'd pay the price, too).

Related: What Is Comedian, Dane Cook Up To Today?

Darryl Stole Millions From Dane Cook

In 2010, Boston Globe reported that Dane Cook's half-brother had embezzled millions from the famous comedian. Between 2004 and 2008, Darryl funneled millions of dollars into his personal accounts.

He bought properties and "several business ventures" with the money, the publication wrote. When the news broke, Boston Globe noted that Darryl McCauley "was involved in Cook’s career from the start, selling merchandise at shows and managing his e-mail list and website."

So maybe Dane's half-brother thought he was entitled to a bigger payoff than the $150K per year he was earning as a business manager? He sure thought so; forging over $3 million in checks was part of the scam, but the amount embezzled came to be even more than that!

Fortunately, as Celebrity Net Worth confirmed, Dane is now worth about $35 million. Clearly, he was able to recoup a lot of the money his half-brother stole. In the meantime, Darryl went to prison with a sentence carrying five to six years. His wife was also sentenced to a few years in prison. Additionally, the duo was ordered to repay $12 million, proving just how much they managed to steal from Cook. Yikes!

Related: Here's How Comedian Dane Cook Spends His $35 Million Net Worth

Does Dane Cook Speak To His Brother Today?

As for the pair's relationship today, Redditors point to interviews Dane's given on the subject. When asked about the events that went down due to Darryl's betrayal, Dane says he "loved" his brother. As in, past tense.

And fans can agree that having your half-brother steal millions out from under your nose while working for you, day after day and year after year, had to have been rough. It's not surprising there's no family tie there anymore!

Next:Did Dane Cook Ever Get His Money Back From His Brother?