Celebrities that Love to Gamble Header

Gambling is a hobby and a passion for many. Players often view gambling as a form of entertainment, not necessarily a means to make money. Casino games, sports betting, live poker, and other forms of gambling can be exciting. So, it isn’t a surprise really to learn that some of the biggest celebrities love to gamble. Even with millions of dollars in their bank accounts from movies, music, and countless endorsements, gambling is still fun. Want to find out more? Check out our list of the biggest celebrities that gamble regularly.

Michael Jordan

The basketball legend used to enjoy gambling. Jordan used to like betting so much that he would do it on any chance he got. Indeed, this even includes betting on simple games of rock, paper, scissors. Some stories even say that he gambled up to $100,000 on the kid’s game. So naturally, he also spent a lot of time in casinos, betting on actual games. He would drop huge amounts of money at the tables, given his successful basketball career. The NBA star also enjoyed playing golf and gambled massive sums while on the course. One of his fellow NBA players, Charles Barkley, said that Michael Jordan bet $300,000 on a putt once.

Even some of his teammates recalled stories where Jordan would spend entire nights gambling. And sometimes, it would be on the most insane things. For example, he once wagered $900 that his luggage would be the first to arrive at the airport carousel. He won that bet.

Ben Affleck

Ben Affleck is one of the biggest names in Hollywood. He played lead roles in blockbuster movies, directed and produced films, and even dated Jennifer Lopez. However, some people don’t know about his resume is his love for gambling. Affleck really likes playing poker and has participated in some prestigious tournaments over the years. He also enjoyed playing blackjack and was a generous tipper in casinos.

In 2004, Ben Affleck won the Commerce Casino’s California State Poker Championship for over $350,000. He also earned an entry to the 2004 World Poker Tour Championship, worth $25,000. In addition, the actor took part in several World Series of Poker Main Events.

In 2020, Ben Affleck channeled his love for poker into something good. He organized a celebrity poker game online to help raise money for charity during the pandemic. The online poker tournament was called All In For America’s Charity, and players had to donate $10,000 as the buy-in. With live streaming and donations, he managed to raise around $1,750,000. The star-studded lineup included Matt Damon, Adam Sandler, Adam Levine, Tom Brady, Kevin Smith, and Tobey Maguire.

Matt Damon

Matt Damon actually helped set everything up for the online poker tournament for the charity mentioned above. He and Ben Affleck are close friends, so it is only normal to share some of the same passions. Damon loves playing poker and blackjack. He got a taste of poker in the iconic movie Rounders. Matt had professional poker player Johnny Chan show him the ropes to prepare for the role. Surprisingly, he learned so much that he started playing and had success.

He would play in casinos and home games with his celebrity friends. According to stories, the highlight seems to be a private game with a $100,000 buy-in. He hasn’t had the same success in poker tournaments as Ben Affleck. That being said, Matt Damon continues to be one of the biggest celebrities with a love for gambling.


Jay-Z is one of the most iconic names in music. While he has countless fans for his work, not many know about his gambling passion. However, Jay-Z has been enjoying gambling games for quite some time now. He even held his 2019 gala for charity at the Hard Rock Casino. This entailed a high-stakes blackjack tournament to help make things more exciting and raise extra money. Unfortunately, his rapper friend YoGotti lost $500,000 in a single bet during this tournament. Jay-Z’s reaction to this became viral on the internet.

Furthermore, Jay-Z likes playing live poker and online poker to high-stakes blackjack. So, of course, he tends to frequent the high-stakes tables and tournaments. The hip-hop artist has had his fair share of losses at the poker tables. Some reports indicate that he lost almost $1 million in just one hand in Las Vegas. But this didn’t slow him down on his way to becoming the first hip-hop billionaire.

Tobey Maguire

There are definitely some aspects that make people good at acting and live poker both. Being able to control facial expressions can be very important. You don’t see a lot of successful poker players with clear tells. The next actor on our list with love for poker is none other than Tobey Maguire. Known for his role as Spiderman in the first series, Tobey often takes part in celebrity games. However, according to reports, he isn’t always the most liked player at the table.

Tobey Maguire has been playing poker since he was a teenager. He even has his own story in the book Molly’s Game, which describes players at private poker games. Molly is the person hosting the high-stakes poker games. In the book, he is described as being somewhat of a jerk who likes destroying the lives of other poker players. It is also said that he told Molly to climb on the table and bark for tips.

Paris Hilton

Paris Hilton is a celebrity that spends a lot of time in Las Vegas. She even appeared in some commercials for online casinos where she ran the establishment. The ads promoted new no deposit bonuses for new players. These online casino promotions can be great for users since they are easy to claim and find if you know where to look. Moreover, online casinos can offer free funds and free spins just for signing up. Not to mention that welcome bonuses can double your bankroll in an instant.

Of course, Paris already has a lot of money and enjoys the thrill of gambling. As a result, she drops $30,000 on casino games in Sin City. She even won $50,000 at the blackjack tables. Paris also likes playing high-stakes poker and participates in exclusive celebrity games in New York City. In 2006, Paris Hilton reportedly lost her custom Bentley in a high-stakes poker game.

Another gambling tidbit worth mentioning is that Paris is banned for life from two Wynn casinos. The celebrity was caught with illegal substances on the premises and was put on the blacklist.

Brad Pitt

Brad Pitt is one of the most prominent movie stars in the world. Among his most successful films are the Ocean’s series. Here, he plays the role of an experienced gambler/robber. He spent quite a bit of time in casinos for the original Ocean’s Eleven and the sequels. At this time, he fell in love with gambling, and he continues to frequent casinos to this day.

Pitt’s favorite games are poker, blackjack, and slot machines. He even plays slots online where legal. The actor said he likes the thrill that the games provide and will continue to play his favorites. Despite that, he gambles responsibly and doesn’t usually place large wagers.

George Clooney

After mentioning Brad Pitt, we have to talk about his co-star, Mr. Ocean himself. George Clooney is one of the regulars at Molly’s private high-stakes poker games. We mentioned them previously with Tobey Maguire, and Clooney is up there with the most active players. George Clooney’s love for gambling is not something new. He has been playing casino games since he was of legal age.

If truth be told, Clooney even showed interest in building a casino in Vegas, but he never carried out the plans. Even after he invested millions of dollars into the project, the gamble didn’t pay off in the end. Hopefully, he will revisit this in the future, and we will get a Clooney-owned casino in Las Vegas.

50 Cent

50 Cent is known as a rapper, but he is also one of the biggest celebrity gamblers. Unlike most other mentions on our list, 50 Cent enjoys betting vast sums of money on sports. And when we say huge sums, we mean seven figures on a single sporting event. It is said that 50 Cent placed a bet of $2 million on Floyd Mayweather to beat Manny Pacquiao. He won that bet. 50 Cent also won $500,000 from a bet on the New York Giants against the San Francisco 49ers.

And these are only some of the bets that he talked about on his Twitter. It is safe to say that he is an avid gambler who likes the NFL and boxing.

Charlie Sheen

Charlie Sheen is probably best known for his role in the TV series Two and a Half Men. Nevertheless, the actor played a role that resembled his real life, with loads of alcohol, women, and gambling. As a matter of fact, reports indicate that Charlie Sheen was really into sports betting for a while. He was even placing bets over the phone while going to the hospital for the birth of his child. Other rumors place him in the middle of a betting ring run by the Mafia. His ex-wife also stated that Charlie would bet $200,000 on sports every week.

He did have some success with betting over the years. One of his biggest wins was a boxing match between Manny Pacquiao and Oscar De La Hoya. The actor put down an impressive $1 million on Pacquiao to win, which he did. But, oddly enough, Sheen wasn’t thrilled about the massive win in his statement. Not long after that, the actor declared that he was a retired gambler.

Ashton Kutcher

Most celebrities that gamble do it for the thrill. They have money and can afford to place some large bets, be it on casino games or sports. But, as we’ve seen from the list so far, most of them don’t really have a strategy. They like to gamble, and that is pretty much it. Ashton Kutcher, however, is in a different league in this regard. The famous actor is one of the best celebrities when it comes to sports betting. He uses mathematics and statistics to make decisions, not just pure intuition.

Ashton Kutcher’s approach to sports betting strategies has been quite successful. He was even placing bets for the largest sports betting syndicate in the US. According to an interview for Esquire Magazine, the actor helped clear $750,000 in just four weeks of college football. Unfortunately, he was so good that the bookmakers prevented him from placing large wagers.

Tiger Woods

As one of the most famous golf players ever, Tiger Woods is a full-fledged celebrity who loves to gamble. He used to host an annual event where he would invite other celebrities and play golf, poker, and party. Some professional poker players were on the invite list, showing that Woods isn’t afraid of some competition. Nonetheless, he generally held his own and performed well at the poker table of most of these events.

Tiger Woods also likes playing blackjack, and he is very good at it. He plays for high stakes in casinos and also hosts it at his events from time to time. Phill Hellmuth, a renowned poker player with 13 WSOP bracelets, said Tiger gave him helpful blackjack advice.

Floyd Mayweather

We end the list of gambling celebrities with arguably the biggest gambler out of all of them. Many people know Floyd Mayweather as the best professional boxer of all time. He has made close to $1 billion during his boxing career, and he hasn’t been shy about his spending habits. “Money” Mayweather often posted his bet slips online, showing massive wagers of around $1 million. In the early 2010s, he stated that he was on a winning streak of 46 bets. He collected almost $4 million in profits from this remarkable run. In 2013, Floyd placed a bet of $5.9 million on the Miami Heat against the Indian Pacers. He won and made a profit of $6.5 million.

In 2017, Floyd wanted to place a $400,000 bet on himself to beat Conor McGregor. However, the Las Vegas bookmaker wished to perform some legal checks. Consequently, this annoyed Mayweather, and he left before placing the wager. It’s unfortunate seeing that he won that fight with a KO against the UFC fighter.