When it comes to your average comedian, making a healthy living while building up a minor fan following is the best they can reasonably hope for. On the other end of the spectrum, every generation of comedians seems to have a select few performers that come along and become an absolute sensation. For example, over the last several years people like Dave Chappelle, Amy Schumer, and Kevin Hart all have made a massive amount of money as comedians.

Even though it may be hard to remember now, given the fact that he isn’t talked about much these days, in the past Dane Cook was one of the most in-demand comedians around. Unsurprisingly, all of the success that Cook enjoyed resulted in him making an extremely healthy living at the height of his career.

Said to have amassed a $35 million fortune due to the massive success he has enjoyed, it shouldn’t surprise anyone that Dane Cook’s lifestyle is something else. Of course, it still is a lot of fun to examine some of the most notable ways that Cook has spent all of that money.

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Dane’s Incredible Career

After the release of Dane Cook’s comedy album “Retaliation”, which went double platinum, a lot of people seemed to think that he was an overnight success. After all, that feat made Cook the first comedian in 27 years to have an album reach the top 5 on the Billboard charts. However, in reality, Cook had first begun performing comedy on stage 15 years earlier and he’d even released a different album a couple of years earlier.

So incredibly popular at the height of his standup comedy career that he could sell out stadiums, Cook began to branch out into other mediums. Unfortunately, some of his early efforts failed to take off as his attempt to become a sitcom star went nowhere after the pilot of his proposed show, Cooked, wasn’t picked up.

On the other end of the spectrum, Cook’s career began to take off to such a degree that he landed some high profile gigs that every other comedian had to envy. For example, in 2005 Cook hosted an episode of Saturday Night Live, he performed at the 2005 MTV Video Music Awards, and he recorded his first HBO standup comedy special.

Aside from all of the success, Dane Cook enjoyed as a comedian, his biggest career achievement has to be all of the movies he starred in. That is a very big deal considering that historically speaking, for every comedian that makes it as a movie actor, another one fails. First able to land a smaller role in the comedy Mystery Men, before too long Cook played the lead character for the first time when he headlined Employee of the Month. After that initial success, Cook went on to star in a slew of other movies including Good Luck Chuck and My Best Friend's Girl.

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Serious Financial And Personal Hit

Given the fact that Hollywood can be a dog eat dog place, it makes perfect sense that a star like Dane Cook decided to give a member of his family an important role in his new life. Opting to hire his half-brother Darryl McCauley to be his business manager, Cook clearly thought that blood was thicker than money but he turned out to be very wrong.

In charge of the comedian's business life from 2004 until 2008, Dane Cook's half-brother Darryl McCauley stole millions of dollars from him. In fact, McCauley was so brazen about his theft that at one point he wrote a $3 million cheque to himself from Cook’s account. Stealing that kind of money from anyone is brutal enough, but taking that much cash from your half-brother is especially deplorable.

Eventually charged with 27 counts of larceny, Darryl McCauley was sentenced to six years in prison and was ordered to repay $12 million to Dane Cook. That said, it seems extremely unlikely that McCauley will ever come close to making enough money to pay back that kind of sum. Amazingly enough, Cook eventually recovered $800,000 when the police opened up a wall in his brother’s house and found cash he’d stashed there. Speaking about this incident on the Your Mom’s House radio show, Cook revealed his one saving grace was he had $325,000 in stocks which his brother couldn’t steal easily. After selling off that stock, Cook used the cash to rent arenas and put on a comedy tour that helped him to get back on his feet. At least Dane Cook isn't the only star who has faced off against family in court.

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Dane Cook’s Spending

Ever since Dane Cook was forced to rebuild his life, he has been much more focused on living a healthy lifestyle and keeping his priorities straight. That is a great thing since so many star have gone broke buying things they didn't need. Of course, Cook is still happy to spend his 36 million dollar fortune on the things that make him happy. For instance, Dane Cook owns not one, but two Lamborghini Huracans and a Ducati motorcycle.

As for the place that he calls home, in 2008 Dane Cook bought a 4,405-square-foot house in Los Angeles' Hollywood Hills for the reported sum of $7,078,000. A four-bedroom, three and a half-bath home that according to its listing contained a “resort-style” entertainment area, Cook continues to live there to this day.

Aside from Dane Cook’s impressive home and vehicles, it is clear that he loves to travel with his girlfriend and his other loved ones. Not one to be cheap about his vacations, Cook has posted photos of himself boarding a private jet with his traveling partners.

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