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Top Gamblers in Hollywood: From the Red Carpet to the Poker Table

  • 🎬 Star Gamblers: Ben Affleck and Matt Damon showcase exceptional gambling skills, matching their on-screen talents.
  • 🃏 Celebrity Poker: Tobey Maguire's high-stakes games and Jennifer Tilly's poker triumphs highlight Hollywood's poker scene.
  • 💰 Big Wins: Stories of massive wins - Affleck's $800,000 blackjack success and 50 Cent's sports betting victories.
  • 🚫 Gambling Controversies: Affleck's card counting get him banned from a Las Vegas casino..
  • 🌟 Glamour Meets Risk: Hollywood stars bring their charisma to the high-stakes, thrilling world of gambling.

Did you know that some of Hollywood's biggest stars are not just experts in front of the camera but also at the gambling table? From high-stakes poker games to unforgettable casino nights, these celebrities bring the same passion and skill to gambling as they do to their performances. Let's dive into the fascinating world of Hollywood's most notable gamblers.

    1. Ben Affleck

Not only is he celebrated for his achievements in film, but Affleck also stands out in the poker world. In 2001, he showcased his blackjack skills by winning $800,000 in a single night, impressively playing three hands simultaneously, each valued at $20,000. His 2004 victory in the California State Poker Championship not only added $356,400 to his winnings but also earned him a spot in the World Poker Tour championship that year. 

ben affleck actor

Additionally, in 2014, Affleck made headlines when he was banned from playing blackjack at the Hard Rock Cafe in Vegas. This incident occurred after he was caught counting cards, a strategy that, while not illegal, is often frowned upon by casinos. And although there were rumors that he has a gambling addiction problem, the actor has firmly denied those types of allegations. Affleck's adventures in gambling reveal a fascinating side to the actor, one that combines skill, strategy, and a flair for high-stakes games. 

    2. Matt Damon

Matt Damon is not just an Oscar-winning actor, he's also a seasoned poker player. His role in one of the most iconic gambling movies "Rounders" (1998) wasn't just an act, Damon reportedly spent $25,000 on poker games to prepare for his role, showcasing his dedication both on and off the screen. 

To authentically portray his character, he got deep into the world of poker, playing real games and  sharpening his skills against experienced players. This dedication paid off, as Damon didn't just act the part of a poker player, he lived it, bringing an authenticity to his role. His involvement in the poker scene didn't end with the movie. Damon continued to enjoy the game, participating in various poker events and tournaments. 

    3. Tobey Maguire

Tobey Maguire, best known for his role as Spider-Man, is also a high-stakes poker player. He was the mastermind behind some of the most exclusive and lucrative private poker games in Hollywood in the early 2000s. These games, held in luxurious locations like the Beverly Hills Four Seasons Hotel and the Viper Room nightclub, were frequented by a host of celebrities and affluent figures. 

tobey maguire actor

The games, which were the inspiration for the popular gambling movieMolly's Game, were known for their high stakes and were a mix of seasoned players and wealthy individuals. The poker games eventually led to legal consequences. Maguire and other players were caught up in lawsuits related to a Ponzi scheme, with Maguire settling his part for $80,000.

    4. Shannon Elizabeth

Shannon Elizabeth, best known for her role in American Pie, has also made a significant mark in the world of professional poker. Elizabeth's transition from Hollywood actress to poker pro is not just a side hobby but a demonstration of her serious commitment and skill in the game.

Known for her sharp poker abilities, Elizabeth has been a formidable presence in numerous major tournaments. She has cashed four times in the World Series of Poker (WSOP) and has had multiple successes in other significant poker events. Her skill at the poker table caught the public's eye when she reached the semi-finals of the 2007 NBC National Heads-Up Poker Championship, defeating poker pros along the way.

    5. Charlie Sheen

Charlie Sheen, known for his roles in popular TV shows and movies, has a notable history with gambling, especially with sports betting. His ex-wife Denise Richards highlighted Sheen's gambling addiction during their divorce proceedings in 2006, revealing that he was betting around $200,000 every week

charlie sheen actor sitting on stage

One of the most striking incidents in Sheen's gambling history was when he placed a $1 million bet on the boxing match between Manny Pacquiao and Oscar De La Hoya. Despite winning this substantial bet, Sheen's reaction was surprisingly indifferent, suggesting a complex relationship with gambling. Eventually, Sheen decided to quit gambling. In an interview with the New York Times, he described himself as a retired gambler, distinguishing this from being a recovering gambler. 

    6. Jennifer Tilly

Tilly was first introduced to poker by her father, who was a gambler and poker player himself. This early exposure led to a lifelong love for the game. She was given the video game World Series of Poker, which further sparked her interest in the real game.

Tilly's first significant success in poker came in 2005 when she won the $1,000 WSOP Ladies Only Event, pocketing $158,335 and beating a field of 601 female poker players. Despite announcing her retirement from professional poker in 2008 to focus on acting, Tilly continued to play poker as a hobby. She frequently appeared on televised poker shows such as Poker After Dark, Friday Night Poker, and Poker Night in America, using her celebrity status to enhance her brand and poker career.

    7. 50 Cent

Curtis James Jackson III, also known as 50 Cent, is well-known for his gambling exploits, particularly in the world of sports betting. His most notable bets include winning $500,000 on a New York Giants game and then doubling down with a $1 million bet on them in the Super Bowl, which they won. He's also known for a Twitter wager related to a Super Bowl game and a claimed $1 million boxing match bet, though the legitimacy of this bet is uncertain. 

50 cent singing on stage

Additionally, 50 Cent once challenged boxer Floyd Mayweather to read a page of a Harry Potter book without stuttering, offering to donate $750,000 to charity, which Mayweather did not accept. These incidents showcase 50 Cent's fondness for high-stakes betting and his larger-than-life persona.

    8. Pamela Anderson

Pamela Anderson, renowned for her role in Baywatch is also notable for her ventures in the gambling world. While not as frequent a player as some other celebrity gamblers, she has been spotted engaging in various games like blackjack, poker, slots, and baccarat at Las Vegas casinos, popular among A-list celebrities.

One significant moment that caught the poker community's attention was when she lost $250,000 to her ex-husband, Rick Salomon, in a single poker session. This incident was particularly noteworthy, given Salomon's reputation in the poker world, including his substantial win of $2.8 million in the World Series of Poker Big One for One Drop tournament. This event unfolded around the time Anderson filed for divorce from Salomon.

Hollywood's High Rollers: A Final Reflection

This journey through the gambling escapades of Hollywood's elite reveals more than just a penchant for high stakes, it uncovers a parallel universe where skill, luck, and thrill intertwine. From Ben Affleck's strategic blackjack plays to Jennifer Tilly's poker prowess, these celebrities blur the lines between their cinematic personas and their real-life gambling ventures. Their stories, marked by both triumphs and challenges, reflect a fascinating blend of the glamor of Hollywood and the unpredictable world of gambling.

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