Betting isn’t just for the average Joe. In fact, it’s well-known that some celebrities can’t resist the allure of the tables, poker games, or placing high-stakes bets. While you might indulge in a casual weekend wager, some of these celebrities take gambling to an entirely new level.

From Hollywood to Sports Stars, Betting Knows No Bounds

Let’s dive into some of the most notable celebrity gamblers and hear their stories:

1. Michael Jordan

Arguably the greatest basketball player ever, MJ’s love for gambling is legendary. From golf to cards, he’s been known to bet big, sometimes with stakes as high as his NBA games.

2. Ben Affleck

A known face at the poker and blackjack tables, Affleck’s gambling skills are so renowned that he was once asked to refrain from playing blackjack at a casino due to his exceptional ability.

3. Tiger Woods

Outside the golf course, Woods is known to take to the blackjack tables. In Vegas, he’s rumored to have had a $1 million betting limit at the MGM Grand.

4. Charlie Sheen

At the peak of his TV career, Sheen was reportedly spending huge amounts on sports betting, with claims that he once dished out $200,000 in just a week.

5. Michael Phelps

The record-breaking Olympian swaps pools for poker tables occasionally. He’s played at the World Series of Poker, bringing his competitive spirit to the card table.

6. Jennifer Tilly

Beyond her acting accolades, Tilly shines at poker. She clinched a World Series of Poker bracelet in 2005, proving her prowess.

7. Toby McGuire

Beyond his web-slinging fame, McGuire is a fixture in high-stakes poker games, often going head-to-head with other celebrities and professional players.

8. Ashton Kutcher

This actor and entrepreneur once fronted for a massive sports betting syndicate. Kutcher used his celebrity to distract bookies while placing big bets for a group of professional bettors.

9. Pamela Anderson

The Baywatch star’s gambling tales have a romantic twist. Legend has it she once settled a poker debt with a spontaneous marriage proposal!

10. 50 Cent

The rapper’s risk-taking isn’t limited to his music career. He reportedly once pocketed $500,000 from a single NFL game bet.

11. Dana White

UFC president Dana White is a skilled gambler, often winning big at blackjack, even up to $5 million in a night. Betting $50,000 per hand, several casinos have banned him due to significant losses on their end. Despite controversy over UFC fighter pay, White doesn’t shy away from high-stakes gambling.


12. Shannon Elizabeth

Best known for her role in “American Pie”, Shannon transitioned from Hollywood to poker tables. She’s become a recognized poker player and has participated in major tournaments, turning her hobby into a semi-professional pursuit.

13. Charles Barkley

The NBA Hall of Famer openly admits to his love for gambling. While he’s won big, he’s also experienced significant losses, reminding us of the unpredictable nature of betting.

14. Phil Mickelson

Golf isn’t the only game Phil’s good at. He’s known for making sizeable sports bets, notably winning big by betting on the Baltimore Ravens in 2001.

15. Drake

The rapper isn’t shy about flashing his cash, and that extends to the gambling world. He reportedly once dropped a cool $200,000 at a casino in Atlantic City in one night.

16. Bryan “Birdman” Williams

The co-founder of Cash Money Records is as bold with his bets as he is with his music decisions. He’s known to have made million-dollar bets on the Super Bowl.

17. Floyd Mayweather Jr.

Known as “Money” Mayweather for a reason, the boxing champ is renowned for flaunting his winnings, especially from sports bets. His Instagram showcases his six and seven-figure betting slips.

18. Alan Iverson

One of NBA’s brightest stars, Iverson’s skills on the court were unmatched. Off it, he had a penchant for casinos, often seen at the high roller tables.

19. Jaromir Jagr

The NHL legend found himself in headlines not just for his on-ice prowess but also for his gambling debts. However, he’s always been open about his love for betting.

20. Aaron Paul

The “Breaking Bad” star is an avid poker player. He’s participated in the World Series of Poker and even played against poker legends for charity.

21. Gladys Knight

The Empress of Soul, Knight confessed to her gambling addiction in her memoir. However, she successfully overcame it and continues to inspire many.

NFL King of the Hill 2023

From Courts to Cards, They Play to Win

From the courtside to the poker tables, these celebrities have shown that the thrill of the game isn’t limited to their professional lives. However, just as in their careers, wins and losses are part and parcel of the gamble. Always remember to approach betting with caution and responsibility.

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