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High-Stakes Drama: Celebrities Who Love Gambling

Gambling is a popular pastime for many. Just as you enjoy playing games at, celebrities also relish visiting casinos. From actors to musicians, many stars find the thrill of gambling irresistible. Here, we delve into the lives of some well-known celebrity gamblers, their favorite games, and some of their most memorable wins and losses.

Memorable Wins and Losses


  • 50 Cent: Known for his bold bets, 50 Cent once placed a bet up to $2 million against Manny Pacquiao and won. His fearless approach to gambling has earned him a reputation as a high-stakes player​​.
  • Ben Affleck: Affleck is a skilled poker player, winning the California State Poker Championship in 2004
  • Tiger Woods: Known for his high-stakes blackjack sessions, Woods often bets up to $25,000 per hand and has won substantial amounts​


  • Charlie Sheen: Sheen’s gambling habits are infamous. He reportedly bet $1 million on a boxing match and, despite winning, he described feeling no joy from the win, highlighting the potential emptiness of habitual gambling​.
  • Tiger Woods: His gambling habits have led to losses, but details remain private. However, his $1 million upper betting limit at MGM Grand suggests he can afford substantial losses​

Top Celebrity Gamblers and Their Stories

1. George Clooney

George Clooney, famous for his suave demeanor and roles in movies like “Ocean’s Eleven,” mirrors his on-screen character off-screen. Clooney has been seen at various high-end casinos, engaging in blackjack and poker. Beyond playing, he also co-owned a Las Vegas casino resort, which underscores his deep ties to the gambling world​.

2. Brad Pitt

Brad Pitt’s interest in gambling sparked during his preparation for the movie “Ocean’s Eleven.” He discovered a passion for poker, blackjack, and slots. Pitt enjoys the excitement and challenge these games offer and continues to indulge in them both online and offline.

3. Paris Hilton

Paris Hilton is a regular in Las Vegas, the gambling capital. She enjoys both offline and online casino games, often spotted in high-stakes poker games. Hilton’s gambling endeavors have seen her win substantial amounts, adding to her celebrity allure.

Shannon Elizabeth: Transitioning from actress to poker player, Elizabeth has made a significant mark in the poker community. Her participation in tournaments like the World Series of Poker showcases her skills and dedication​.

4. Tiger Woods

Known for his competitive nature, Woods takes this drive to the blackjack table. He has a high betting limit at The Mansion, an MGM Grand Casino club for high-rollers, demonstrating his serious approach to gambling​.

5. Allen Iverson

Iverson’s gambling habits are well-known in the sports world. Despite earning millions during his career, his love for gambling led to significant financial troubles, highlighting the risks involved.

6. Michael Jordan

Michael Jordan, renowned for his legendary basketball career also has a well-documented history of high-stakes gambling. In his 1993 book, San Diego businessman Richard Esquinas detailed how he and Jordan frequently bet against each other while golfing. These bets sometimes involved $100,000 putts, and on one occasion, Jordan reportedly lost $1.25 million to Esquinas through a series of golf bets.

7. Tiger Woods

Tiger Woods, renowned for his golf achievements and inducted into the World Golf Hall of Fame in 2021, has had a tumultuous personal life. Amid scandals and legal issues, Woods has channeled his competitive nature into gambling, particularly blackjack. He has reportedly won significant sums and was once a frequent visitor to Las Vegas casinos, although he has scaled back his visits recently.

Reasons Celebrities Love Gambling

Although many admire celebrities for their extravagant partying and exotic travels, few realize how much they like gambling and why.

Abundance of WealthCelebrities often have tens of millions of dollars, leading them to gamble for fun rather than profit. Casinos offer exclusivity and glamour that attract wealthy individuals.
Financial AmbitionsSome celebrities gamble to increase their wealth, driven by their egos and the thrill of potentially winning big.
Competitive NatureGambling provides a rush and satisfies the competitive nature of celebrities, who enjoy the thrill of winning.
Too Much DowntimeCelebrities often have significant downtime during filming or touring, leading them to gamble to pass the time.
Character PreparationSome celebrities start gambling to better understand and portray their characters in films about gambling.

Wrapping Up

To sum up, the gambling world isn’t just for regular people. Hollywood, music, and sports stars aren’t the only ones who like the rush of betting.

In addition to captivating audiences with their talents, these celebrities flaunt their passion of gambling. It’s a reminder that even the most accomplished and renowned people find thrill and pleasure in games of chance.

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