Rolling the Dice: 10 Famous Faces Who Love to Bet
Gambling has always been a popular pastime among the rich and famous, and many celebrity gamblers have been known to indulge in various forms of gambling, from poker to sports betting to casino games. Some celebrities have even become known for their gambling habits, either because of their prowess at the tables or because of their high-stakes bets.
Here are ten celebrities who have been known to enjoy celebrities gambling, each with their own unique style and approach to the world of celebrities betting.
Charlie Sheen
Charlie Sheen is a well-known actor who has been involved in various controversies throughout his career, including his gambling habit. Sheen is one of many celebrity gamblers who has been known to gamble large sums of money on various games, including blackjack, craps, and sports betting. He has been reported to have lost millions of dollars due to his gambling addiction.
Sheen’s struggles with addiction have been well-documented, and his gambling habit is just one of many issues he has faced over the years. Despite the negative consequences of his behavior, Sheen has continued to gamble and has even been seen at casinos recently.
Drake
There have been rumors and reports of Drake, the Canadian rapper and songwriter, engaging in high-stakes betting activities. In 2019, it was reported that he had won $200,000 while playing blackjack at a casino in Atlantic City. Drake has also been spotted playing poker with other celebrity gamblers, including Ben Affleck and Tobey Maguire, at private games with high buy-ins.
However, it is unclear if Drake has a gambling addiction or if these are isolated incidents of him enjoying the occasional high-stakes game. While he has not publicly addressed his gambling habits, some have expressed concern about the potential negative impact on his finances and overall well-being.
Ben Affleck
Ben Affleck is a well-known actor and filmmaker who has been open about his struggles with gambling addiction, making him one of the most well-known celebrity gamblers. He has been reported to have lost hundreds of thousands of dollars due to his gambling habit, and in 2001, he entered rehab for alcohol addiction and compulsive gambling. In 2014, Affleck was banned from the blackjack tables at the Hard Rock Casino in Las Vegas for counting cards, a technique that is not illegal but is frowned upon by casinos.
Despite the negative consequences of his behavior, Affleck has continued to bet and has been seen playing poker with other celebrities. However, he has also sought help for his addiction and has spoken publicly about the importance of seeking treatment.
Michael Jordan
Michael Jordan, the legendary basketball player, has been known to have a fondness for gambling, making him one of the most high-profile celebrity gamblers. Throughout his career, rumors and stories circulated about his betting habits, particularly on the golf course and at casinos. In 1993, Jordan’s gambling habits made headlines when he was seen playing cards with convicted drug dealer James “Slim” Bouler. This led to an investigation by the NBA, but no wrongdoing was found.
Jordan has also been known to place large bets on golf games, and his competitive nature and love of the game have been cited as contributing factors to his gambling. Despite the controversies surrounding his bettings, Jordan has remained one of the most popular and successful athletes of all time, both on and off the court.
Matt Damon
Matt Damon, the famous Hollywood actor, has been known to have an interest in gambling, making him one of the most well-known celebrity gamblers in Hollywood. He is a regular at high-stakes poker games and has even played in the World Series of Poker. Damon’s passion for gambling is not limited to just poker, as he has also been spotted at various casinos around the world, including Las Vegas and Monte Carlo. In fact, his role in the 1998 movie “Rounders” helped to popularize the game of Texas Hold’em and poker culture in general.
However, despite his love for gambling, Damon has also been vocal about the need for responsible gambling and the dangers of addiction. He has been involved in various charitable causes related to problem gambling, including the annual Ante Up for Africa charity poker tournament.
50 Cent
Curtis “50 Cent” Jackson, the rapper, actor, and entrepreneur, has been known to enjoy gambling, particularly in the realm of sports betting. He has been spotted at several high-stakes sportsbooks, including in Las Vegas, where he has placed bets on a variety of sports, including boxing and basketball. In fact, 50 Cent has been known to make sizable bets, such as a reported $500,000 wager on the 2012 Super Bowl. Beyond sports betting, he has also been associated with casino gambling and has appeared in commercials for online gambling sites.
While 50 Cent has not been immune to the pitfalls of gambling, including a 2015 lawsuit related to a failed joint venture with a sports betting company, he has remained a successful and influential figure in entertainment and entrepreneurship.
Paris Hilton
Paris Hilton, the socialite, model, and reality TV star, has been known to enjoy gambling on occasion. She has been spotted at several casinos around the world, including in Las Vegas, where she has been known to place bets on table games and slot machines. Hilton has also made several appearances at high-profile poker tournaments, such as the World Series of Poker, and has even hosted her own charity poker event.
While she has not been associated with any major gambling controversies, Hilton has had her share of legal troubles over the years, including a 2010 arrest for cocaine possession in Las Vegas. Despite this, she has remained a prominent figure in entertainment, and has used her platform to advocate for a range of causes, from animal rights to LGBTQ rights.
Tobey Maguire
Tobey Maguire, the actor best known for his portrayal of Spider-Man in the early 2000s, has been known to have a strong interest in gambling, particularly in the realm of high-stakes poker. He has been a regular at underground poker games that have included celebrities, hedge fund managers, and other high rollers, and has even won large sums of money at these events.
However, Maguire’s gambling activities have also been the subject of controversy. In 2011, he was sued by a group of investors who alleged that he had won more than $300,000 in an illegal poker game that was backed by a Ponzi scheme. Maguire ultimately settled the lawsuit for an undisclosed sum. Despite this, he has remained a successful and popular figure in entertainment, with a range of acting and producing credits to his name.
Lady Gaga
Lady Gaga, the Grammy Award-winning singer, songwriter, and actress, has been known to have a fondness for gambling. She has been spotted at several casinos around the world, including in Las Vegas, where she has been known to play slot machines and other casino games. In fact, she even wrote a song about the experience, “Poker Face,” which became a massive hit in 2008. Gaga has also been involved in several gambling-related promotions, including a 2014 collaboration with Zynga Poker, an online poker game.
While her interest in gambling has not been associated with any major controversies, she has been open about her struggles with addiction, including with drugs and alcohol. Despite these challenges, Lady Gaga has remained a hugely popular and influential figure in music and entertainment, with numerous awards and hit songs to her name.
Brad Pitt
Brad Pitt, the Academy Award-winning actor, has been known to have an interest in gambling, particularly in the realm of sports betting. He has been spotted at several high-stakes sportsbooks, including in Las Vegas, where he has placed bets on a variety of sports, including football and basketball. Pitt has also been associated with casino gambling, and has been spotted playing blackjack and other table games.
While his gambling activities have not been associated with any major controversies, he has been open about his struggles with addiction, including with alcohol and marijuana. Despite these challenges, Pitt has remained a hugely successful and influential figure in Hollywood, with numerous acclaimed performances and producing credits to his name.
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