Gambling has always been a popular pastime, even among celebrities. In this blog post, we will explore the lives of 10 famous celebrity gamblers who have made headlines with their high-stakes bets and impressive wins. From actors to musicians, these individuals have not only achieved success in their respective fields but have also found excitement and fortune at the casino tables.
- Ben Affleck
Ben Affleck is not only known for his successful acting career but also for his love for poker and blackjack. Affleck has been spotted playing in high-stakes poker tournaments and has even won the California State Poker Championship in 2004 that earned him $356,400. However, he has also faced some notable losses, including a reported $400,000 loss in a single night of blackjack.
In 2014, he was banned from playing blackjack at the Hard Rock Café in Vegas after being found for counting cards following several wins.
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- Tobey Maguire
Tobey Maguire, best known for his role as Spider-Man, has also made a name for himself in the world of high-stakes poker. In 2004 at the National Championship of Poker, Maguire won $95,480. Furthermore, Maguire has been involved in underground poker games with other celebrities and professional poker players, including Ben affleck and Leonardo DiCaprio. However, his involvement in these games has not been without controversy, as he was sued for his involvement in an illegal gambling ring.
- Charlie Sheen
Charlie Sheen, one of Hollywood’s highest paid American television actors, is no stranger to the wild side of gambling. The actor has openly admitted to his addiction to gambling and has struggled with it throughout his career. It is reported that Sheen would lose around $200,000 a week due to poor gambling decisions. However, Sheen did have some big wins. His biggest win was from a boxing bout between Manny Pacquiao and Oscar De La Hoya. He put a mind blowing $1 million dollar bet on Pacquiao and won! Sheen’s gambling addiction has had a significant impact on his personal life and career, leading to financial troubles and strained relationships. Inevitably, Sheen retired from gambling in 2012.
- Matt Damon
Matt Damon, known for his roles in movies like “Good Will Hunting” and the “Bourne” series, has a connection to the gambling world through his collaboration with Ben Affleck in the movie “Rounders.” The film revolves around the world of underground poker and has gained a cult following among poker enthusiasts. Damon has also been involved in philanthropic efforts related to gambling, including charity poker tournaments. Furthermore, Damon also participated in several World Series of Poker (WSOP) events and Texas Hold’em games.
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- Pamela Anderson
Pamela Anderson, famous for her role in “Baywatch,” has also found herself drawn to the casino floor. Anderson has expressed her love for poker, blackjack, baccarat, and slot machines and has been known to participate in celebrity poker tournaments. Additionally, she has used her fame and influence to raise money for various charitable causes through poker events.
- Michael Jordan
Michael Jordan, the basketball legend, is known for his competitive nature both on and off the court. Jordan has been rumored to have a passion for gambling, particularly on golf courses. While some of these rumors have been controversial and have impacted his public image, Jordan has always maintained that his gambling habits are within his means and not a cause for concern.
- Ray Romano
Ray Romano, the comedian best known for his role in the sitcom “Everybody Loves Raymond,” has an unexpected passion for gambling. Romano has shared his experiences with sports betting and has even incorporated gambling into his stand-up routines. His comedic take on gambling has resonated with audiences and added a unique element to his performances. However, he sough help from Gamblers Anonymous and has been sober since 1998.
- Shannon Elizabeth
Shannon Elizabeth, known for her roles in movies like “American Pie” and “Scary Movie,” has made a name for herself in the world of professional poker. Elizabeth has achieved success in poker tournaments and has even competed in the World Series of Poker. In the 4th edition of the Celebrity Poker Showdown, she bet out 83 other celebrities to win $50,000. Furthermore, she won 12 poker tournaments between 2006 and 2010.
- Floyd Mayweather Jr.
Floyd Mayweather Jr., the boxing champion, is not only known for his skills in the ring but also for his extravagant bets and wins. Mayweather has been known to place high-stakes bets on various sports events, including boxing matches. His gambling habits have become part of his public persona and have further solidified his status as a high-roller gambler. However, Mayweather’s gambling activities haven’t been all wins, in 2012 he was banned from the Bellagio casino.
- Jennifer Tilly
Jennifer Tilly, an actress known for her roles in movies like “Bride of Chucky” and “Liar Liar,” has successfully transitioned into the world of professional poker. Tilly has achieved notable success in poker tournaments, including winning a World Series of Poker bracelet in 2005. Furthermore, in 2014 she was nominated for PokerListing’s Spirit of Poker Living Legend Award
Final Thoughts
These 10 famous celebrity gamblers have shown that even the rich and famous enjoy the thrill of gambling. From poker to blackjack, their experiences at the casino have added an extra layer of excitement to their already glamorous lives. While some have faced controversies and struggles, others have found success and even used their gambling skills for philanthropic endeavors.
