Top 5 Celebrity Bettors

Being a celebrity means that you can have the best of everything: the fanciest cars, the biggest houses, and the top designer clothes. It also means that you can bet big at the casino if you’re into that sort of thing. And in Hollywood, there is no shortage of people who love to place a wager. 

 

 

Some Hollywood casino enthusiasts are so famous for their exploits that it’s even been immortalized in film. From actors to sports stars, here are the top celebrity bettors whose wagers put everyone else to shame:

• Tobey Maguire

Tobey Maguire might be most famous for playing Spider-Man, but he has also made headlines for his betting escapades. Ironically, it all began right after Spider-Man wrapped, and he was on top of the world. Remember that in 2004, the gambling world was not what it is now. These days, you can go online and access all sorts of gambling sites for every kind of game imaginable, no matter where you live. If you’re in Mississippi, for example, you can easily opt for casino sites for Mississippi residents and have your needs met. The same applies to places like New York, Texas, California, and many more. Then, you had to bet in person, which is what he did. He first tried his hand at professional poker, even attending World Series of Poker (WSOP) events. 

 

But what really made the news was when he began participating in underground high-stakes poker with other Hollywood heavyweights like long-time friend Leo DiCaprio. These games were hosted by Molly Bloom in the 2000s and were eventually turned into a film called Molly’s Game, based on her memoirs and starring Jessica Chastain.

 

• Floyd Mayweather

With an iconic boxing career and a net worth in the hundreds of millions, Floyd Mayweather can more than afford to indulge his love for betting. He’s been known to flex his winning bets on social media, like the time he won $42,500 in profit from a bet on the Bivol vs. Canelo fight. He’s been so successful at betting on NFL and NBA games that he made millions between 2010 and 2012 alone and is perhaps one of the most popular bettors in Hollywood. Even weirder, he’s bet on things like the outcome of a Justin Bieber concert, even while still an active fighter. Needless to say, his love of the game isn’t stopping anytime soon, and neither are the money racks he plasters all over his socials. 

 

• Jennifer Tilly

You might know her best from Bride of Chucky, but Jennifer Tilly has also made a name for herself in the world of professional poker. It all began in her youth, as both her father and an ex-boyfriend were poker players. After her acting career took off, she began playing in the 1990s, and by the 2000s, she became the first celebrity to win a World Series of Poker bracelet. She was even nominated for PokerListings' Spirit of Poker Living Legend Award in 2014, with career earnings over $1 million. She’s one of the biggest bettors in Hollywood because she shows that you can have more than one successful career at any given time. 

 

• Matt Damon

Believe it or not, in another timeline, Matt Damon could have been a star poker player instead of a movie star. In the 1990s (just as his star was starting to rise along with friend Ben Affleck), he took an interest in professional poker and was quite good at it. He competed in the 1998 World Series of Poker (WSOP) but was eliminated by Pro Doyle Brunson. He’s kept at it and even attended the World Series of Poker events in 2010. From what’s been said, he has a true passion for the game, and while his big break has been in film, he plays for fun to this day.

 

• George Clooney

It should come as no surprise that George Clooney is an iconic gambler in Hollywood. After all, he played the role of Danny Ocean in the Ocean’s films, where he tried to pull a heist at a casino. In real life, George Clooney has tried to get into the casino business. He teamed up with business partner Rande Gerber for a casino that was to be named "Las Ramblas" in Las Vegas. Sadly, the $3 billion deal fell through at the last minute. But that was not the end of his betting adventures. He famously bet with fellow actors Michelle Pfeiffer and Nicole Kidman that he would be single and childless by 40, a bet he would win. Since then, he’s not only gotten married and had kids but has also gotten involved in politics and continued to make movies. 

 

Conclusion 

Hollywood has no shortage of bettors, and these include some of the biggest names in the industry. From movie stars who double as poker champions to sports heroes flexing their cash, the list is endless!