In Hollywood, where fortunes are made and lost on the silver screen, some of the most iconic figures in the entertainment industry have also made a name for themselves at the gambling tables. From poker to blackjack and even high-stakes sports betting, Hollywood’s elite has often been drawn to the thrill of gambling.
For some, it’s a way to blow off steam. For others, it’s another arena where they can test their luck and skill. Today, we will delve into the world of Hollywood’s biggest bettors, exploring their backgrounds, gambling habits, and the stories that have made them legends on and off the screen.
Tobey Maguire: The Poker Prodigy
Tobey Maguire, best known for his role as Spider-Man in the early 2000s, is another Hollywood star who has made a name for himself in high-stakes poker. Maguire’s journey into gambling began in the early 2000s, around the same time that poker was experiencing a surge in popularity thanks to the World Series of Poker (WSOP) and the advent of online betting games like online poker.
Maguire quickly became a regular participant in underground poker games in Los Angeles, where the stakes were often astronomical. These games, depicted in the 2017 film Molly’s Game, were hosted by Molly Bloom and attracted some of the biggest names in Hollywood, as well as wealthy business people and professional poker players.
Ben Affleck: The Poker and Blackjack Shark
Ben Affleck is known for his impressive career as an actor, director, and screenwriter, but he’s also made headlines for his love of gambling. Affleck’s affinity for high-stakes poker and blackjack is well-documented, and he has proven to be more than just a casual gambler.
Affleck started making waves in gambling in the early 2000s when he regularly participated in celebrity poker games. These games, which included Hollywood’s elite and professional poker players, were known for their high stakes and intense competition. Affleck’s skills at the poker table quickly became apparent, and in 2004, he won the California State Poker Championship, taking home a $356,000 prize. This victory solidified his reputation as one of Hollywood’s top poker players.
Affleck’s gambling prowess extends beyond poker. He is also known for his skills in blackjack, a game that requires both luck and strategy. In 2014, Affleck made headlines when he was reportedly banned from playing blackjack at the Hard Rock Casino in Las Vegas for being “too good” at the game. According to reports, Affleck was caught card counting, a legal but frowned-upon strategy that gives players an edge over the house.
Charlie Sheen: The Wild Card
Charlie Sheen is no stranger to the headlines, often making news for his tumultuous personal life, which has included struggles with substance abuse, public outbursts, and high-profile relationships. However, Sheen’s penchant for gambling is another aspect of his life that has contributed to his reputation as Hollywood’s “bad boy.”
Sheen has been open about his love of gambling, particularly sports betting. According to various reports, Sheen often bet large sums on baseball, football, and basketball games. His bets were known to reach six figures, and he was said to have a particular fondness for betting on his favourite teams, sometimes with little regard for the odds.
Matt Damon: The Poker Enthusiast
Matt Damon, one of Hollywood’s most beloved actors, is another star passionate about poker. Damon’s love for the game became widely known after his role in the 1998 film Rounders, where he played a talented poker player trying to win big in underground games to pay off his debts.
The film is credited with helping popularise poker in the late 1990s and early 2000s, and Damon became an avid player. He has participated in several World Series of Poker (WSOP) events and is known to play in celebrity poker tournaments and charity events.
Unlike some Hollywood gamblers on this list, Damon is not known for participating in high-stakes games or taking significant risks. Instead, he approaches poker as a social activity and a way to unwind with friends. Damon has often spoken about how much he enjoys the camaraderie and mental challenge of the game.
Michael Jordan: The Ultimate Competitor
While Michael Jordan is best known as one of the greatest basketball players ever, his competitive spirit extends beyond the court and into the gambling world. Jordan’s love for gambling is legendary, and he has been known to bet on everything from golf to poker to high-stakes blackjack.
Jordan’s gambling habits have been the subject of much speculation and controversy over the years. His intense competitiveness, which made him a dominant force in the NBA, also drives his approach to gambling. Jordan is known to bet large sums of money, and his losses have been reported to reach millions of dollars.
Final Words
Gambling has always been a part of the Hollywood lifestyle, attracting stars with its promise of excitement, challenge, and the potential for big wins. For some, like Ben Affleck and Tobey Maguire, gambling is a serious pursuit that requires skill and strategy. For others, like Charlie Sheen and Michael Jordan, it is a way to embrace the thrill of competition and live life on the edge.