10 of the Best and Worst Celebrity Gamblers in 2024

Celebs entertain us all the time but what do they do for fun? Many actors, directors, and athletes turn to gambling in their downtime. Some are surprisingly successful while others are just plain losers. Being that they are usually loaded with money, casinos welcomed them with open arms as long as they are willing to open their wallets. For ordinary people, it’s great fun to watch celebrities sweating at the poker table, casinos made tons of money from players and sponsorships, so it’s a win-win. Except for celebs, of course. Here are some of the great winners and losers among famous people.

1. Ben Affleck

Source: filmdaily.co

The famous actor is regular at the poker table and he’s pretty good at it. People who watched him play live say that if he wasn’t an actor, he could’ve been a very successful poker player. The biggest hand he won was over $800K almost 20 years ago. Another game of his choice was Blackjack, but unfortunately, Affleck was banned from most Blackjack tables for counting cards in the past. Gambling is his passion for a long time and caused quite a stir in his private life. Supposedly, it was the reason his every relationship fell apart along with his marriage with Jennifer Garner with whom he has three children. Still, Ben can be seen at the poker table even today.

2. Tiger Woods

The most recognizable name in golfing is also a gambler. His private life has been dragged by the press for cheating on his wife back in 2009. After his marriage fell apart, Tiger turned to gambling. Unlike Ben Affleck, Woods was not so great at it. The famous golfer played Blackjack exclusively, and more times than not he lost big time. His usual wager was $25K, and the most he lost in one hand was $200K. He still gambles, but the word on the street is that he got wiser and stopped betting large amounts of money.

3. Floyd Mayweather Jr.

Source: reviewjournal.com

Now, there’s a risk-taker. The well-known boxer doesn’t shy away from any challenge betting away millions of dollars. Quite expectedly, he loves sports betting since that’s his field of expertise. Mayweather doesn’t announce his losses publicly so there is no way of knowing how much he lost so far, but he did advertise his winnings that many claims are exaggerated. Supposedly, the biggest winning was $6.5 million. Floyd is famous for betting large sums which he says is part of his public image. So, a bit of a show-off, but on the other hand, he was quite successful.

4. Matt Damon

Another famous actor that is passionate about poker. A regular visitor to the casinos is actually a very good player. Matt is not betting large sums of money, so it’s obvious he has control over his gambling habit. The actor often wagers small amounts, and usually wins. It’s his way of taking some pressure off of his shoulders and earn a few bucks, not that he needs it desperately. Still, just like his friend and fellow actor Ben Affleck, he never skips visiting a casino at least once a week.

5. Paris Hilton

Source: tribun24.com

Born with a silver spoon in her mouth, the famous socialite’s only job is to have fun. Paris is a regular visitor in Las Vegas and an amateur gambler. In other words, she loves the thrill of gambling but she’s not so good at it. It was never publicly announced how much she lost, but she shared her $30K winning a few years back. The celebrity loves Vegas so much that she practically lives there half the time. A decade ago, Paris showed up in Vegas in a “million-dollar dress” made out of poker chips. All in all, she’s not a great gambler, but she sure knows how to have fun.

6. Charles Barkley

The rich and famous basketball player loves to visit Vegas where he regularly sits at the poker tables. He is fully aware that gambling is not something he’s good at, but he doesn’t give up because – in his own words – he can afford it. Barkley is down $10 million so far, but he’s still waiting patiently for that winning hand. Good luck Charles.

7. Tobey Maguire

Source: intelligencer.ca

Tobey is not only famous for his Spiderman movie franchise, but also for his addiction to poker and alcohol. He’s been in a lot of trouble in the past because of his bad habits, that he even got sued for participating in an illegal poker play. However, Tobey is not about to give up any time soon. He is still playing in one of the most luxurious casinos in Vegas and so far, he’s up for $10 million. His losses were never reported.

8. Michael Jordan

The best basketball player of all time for many is also passionate about betting. Jordan loves to play poker, but he’s not the greatest one in this game. He lost thousands of dollars but he’s persistent in his intention to perfect his skills. Jordan is famous for betting all the time even outside the casino, like when golfing with friends. He’s addicted to trying to hit big winning, but so far, it’s been slipping from him.

9. Charlie Sheen

Source: promiflash.de

Gambling is just another vice of the famous actor. He is more known for his scandalous private life and statements than for acting. Besides doing drugs, being addicted to alcohol and sex, he also loves to play poker and bet on sports. Most of his earnings were blown on gambling trying to satisfy his very expensive lust with spending over $10 million per year at the poker table. He is also back in his child support.

10. Allen Iverson

Iverson’s story is a sad reminder of what gambling addiction can do to a person. He was once known as a great basketball player only to end up broke and alone. He left all of his money at the poker table years ago, his wife left him because of his gambling debts, and he lost all sponsorships. Over time, his bizarre behavior, like fighting with casino staff and other players, earned him a ban in most establishments across the country.

Many famous people broke down under the pressure of having loads of money and fame. Some turned to gambling while others found other poisons like alcohol and drugs. In rare instances, they manage to break free from the claws of addictions but many still stay firmly attached to their vices. Continue reading at playamo.com about other celebrities who blew their millions on gambling, and check out some fun online games.

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