Tag Archives: Gamble

The Biggest Celebrity Gamblers

Celebrities are known for their flashy lifestyles, abundant wealth and glamorous wardrobes. As a world-renowned sports star or acting sensation, taking time off is important, and some of the biggest celebs turn to the casino tables for their adrenalin fix. We take a look at the biggest celebrity stars that simply love to gamble.

Ben Affleck


Not only is Ben an accomplished actor and director, he is also a pretty decent Poker player. In 2005, the Dark Knight star won the California State Poker Championships, netting a cool $356,400. He also qualified for a place on the World Poker Tour. His love for gambling also extends to the Blackjack table, where his proficiency is equally impressive. Ben even got so good at Blackjack that he was banned from playing the tables in Vegas!

Floyd Mayweather


As one of the biggest boxing sensations in the history of the sport, Mayweather has plenty of cash to flash. Turns out, he spends his money by making more on sports betting picks. Floyd has become so good at predicting a winner; he reportedly won $1 million on an Oregon vs. Arizona State game.

Tiger Woods

Tiger Woods casino
Source: Ultimate Lifestylist

What drove Tiger to the tables may have been more than the loss of his good reputation and the fact that his golf game is not what it used to be. Whatever his reasons, Tiger is an avid Blackjack enthusiast, dropping thousands of dollars in Vegas at a time. His success is nowhere near that of the pros, but he is reported to have won over a million dollars at the Mansion at MGM.

Toby Maguire


Toby is an accomplished actor, most famously known for his role as Spiderman. Such is his love for gambling that he hired professional tutors to improve his game before hitting the tables with thousands of dollars lining his pockets. His tutoring sessions must have paid off as he has seen his fair share of winnings and even been sued for participating in an illegal gambling ring.

Pamela Anderson

Pamela Anderson
Source: IMS Vintage Photos

Known for her role as the buxom C.J Parker in Baywatch, Pamela Anderson has plenty of cash in the bank and a keen interest in Poker. Plus, she’s even had a casino online game designed around her likeness! She can be found at the Poker tables at all the most popular casinos around the States and Canada. Her love for the game has got her into trouble more than a few times, and has even reportedly resulted in a marriage proposal.

Charles Barkley


Barkley is a former NBA player and outspoken sports analyst. Unlike Mayweather, he gets his gambling fix at the tables, with Roulette, and Blackjack being his favourites. Barkley is not particularly good at gambling and became addicted to the thrill of trying to win it all back again. In a recent interview, the sports star admitted that his gambling addiction cost him over $10 million over the years.

50 Cent


Singer, songwriter and cultural celebrity, 50 Cent has seen his fair share of luck. Having been shot 9 times and still becoming a world-renowned rapper, Curtis James Jackson III has a keen sense of intuition. While he may be known for making millions on cryptocurrency, 50 Cent is also a proficient sports bettor. In fact, his wagers are the largest anyone has ever seen. In 2012, he reportedly dropped 500k on sports Championship wager between the San Francisco 49ers and New York Giants.

Matt Damon


Like his pal Ben Affleck, Matt is an accomplished actor and producer, with an Oscar to his name. His most notable roles were in Good Will Hunting, the Bourne Identity and the Martian. Matt reportedly spent over $25,000 at the tables in preparation for his role as a Poker player in the movie Rounders and he’s credited the movie with teaching him a few good cheats. His love for gambling also extends to Blackjack, but as yet he hasn’t been banned from any prestigious venues…unlike his buddy Ben!