Famous Celebrities Who Love to Gamble

Famous Celebrities Who Love to Gamble

The funny thing about some of the most successful people in the world is that they love to gamble. Of course, there are people who can’t control their gambling habits, but the biggest winners in the world are risk-takers, and gamblers are risk-takers. 

Before getting to a more detailed list, consider that , Tiger Woods, and Michael Phelps all love to gamble. That should tell you something about the mindset of those who love to gamble. Now let’s get to a list of some other celebrities that love to gamble, as well as some interesting backgrounds or stories to go with them. 

Charlie Sheen

Let’s begin with one of the most interesting celebrities in the world, Charlie Sheen. This dude has been in many movies, including Platoon, Wall Street, Major League, Hot Shots, and Eight Men Out. However, he is best known for his role in the television show, Two and a Half Men, where he earns . This leaves him with plenty of left over money for gambling. 

Sheen is famous for loving to gamble. People who love to win can’t get enough of it. Like many gambling celebrities, Charlie Sheen loves to bet on sports. His ex-wife, Denise Richards, said he was betting $20,000 per week on sports, which is where most of his gambling losses came from. At $1.8 million per episode for Two and a Half Men, I’m willing to wager he’ll be okay.

Ray Romano

Ray Romano is another interesting gambling story. He has an addiction to gambling, but he has learned to control it. It has been such a big part of his life that he created a television series about it, which was called Men of a Certain Age. It only ran for 22 episodes on TNT from 2009-2011, where Ray played Joe Tranelli. Our hero wanted to be a pro golfer but failed and ended up working at a supply store. Since he couldn’t play golf on a professional level and wanted the competition, he went to gambling. This also played a role in his separation and later divorce from his wife. 

Ben Affleck

Ben Affleck also loves to gamble. In 2001, Affleck had a stint in rehab for substance abuse. Ben has been known to frequent casino poker rooms with Matt Damon. For those who don’t know, both of them broke onto the Hollywood scene with Good Will Hunting, which they wrote together. Matt Damon might be known for being a professional poker player in Rounders, but Ben Affleck has had more real life success on the felt. 

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In 2014 Affleck even won the California State Poker Championship. On a somewhat related note, Ben was banned from a Vegas casino in 2014 for winning too much at the blackjack table. Many players like Ben stated playing at online casinos by using an online wallet like . Using these e-wallets give online players all the same competitive play as traditional casinos from the comfort of your home. 

50 Cent

50 Cent is another interesting celebrity with a unique background. 50 Cent showed what his life was like in Get Rich or Die Tryin’. He lived his life on the edge at that time and could have been killed, but he made it through and went on to become a famous rapper and then an actor. His extreme ways are also what led to him betting $2 million on Floyd Mayweather when he fought Manny Pacquiao. He won that bet. It looks like 50 Cent got rich.

Toby Macguire 

Let’s not forget Tobey Macguire. Yes, Spider-Man. Tobey also loves to gamble. He loves to gamble and play poker so much that he was trained by professional poker player Daniel Negreanu. However, it’s possible that Tobey might love to gamble too much. He was part of an illegal gambling ring in 2011. 

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The truth is that Tobey didn’t do anything wrong. The only error he made was crushing a hedge fund manager so badly at the poker table that the hedge fund manager had to start running a ponzi scheme with his investors in order to pay off his debts. When the hedge fund manager got in trouble with the law, Tobey was dragged into the situation. I’d say it was worth the publicity because now we all know that Tobey is a strong competitor on the felt. 

Here’s the bottom line. If you love to gamble, you’re in good company. 

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