Hollywood’s High Rollers: Celebrity Gamblers

Hollywood high rollers have always been surrounded by a certain degree of intrigue and mystique. There is something so titillating about the suave high roller sitting down at a Blackjack table and placing an enormous bet, knowing that they could lose every dime in the blink of an eye. Avid gamblers such as Ben Affleck, Jennifer Tilly, and even John McCain have enjoyed the thrill associated with games of chance. Here are some of Lady Luck’s most notorious celebrity gamblers.

Ashton Kutcher

While Ashton Kutcher is best known for his lovable onscreen characters, he has also had a separate identity in the world of professional sports betting. The actor openly admits that there was a time when he acted as a front for one of the largest sports-betting organizations in America, by simply placing bets on their behalf. Unfortunately, Kutcher was caught but not before clearing $750,000 on college football.

Jennifer Tilly

A beautiful and successfully actress, Jennifer Tilly is the unlikely queen of the poker table. In 2005, she walked away from the World Series of Poker as the Ladies champion. During the championship event, Tilly won over $150,000 in Texas Hold’em from 600 other competitors, walking away with the Ladies’ bracelet. Tilly is an avid gambler who takes her craft seriously. She was even featured in Card Player Magazine as its cover model.

Ben Affleck and Matt Damon

Ben Affleck and Matt Damon are part of one of Hollywood’s most famous friendships. It seems that in addition to the multitude of films that they have worked on together, the pair also enjoys a good game of chance. In fact, Affleck and Damon were part of a handful of celebrities busted for taking part in an illegal underground Poker ring. With a $100,000 buy-in, the event was hosted in a Beverly Hills mansion boasting an exclusive guest list. Affleck and Damon are also keen Blackjack players. The pair were able to successfully play three hands worth $20,000, walking away from a Las Vegas table with over $800,000.

50 Cent

While most gamblers try to develop a system, 50 Cent likes to rely on the voice inside his head to place his bets. He explains that he just has a feeling about who to bet on and he does it. In the boxing match between Oscar De La Hoya and Floyd Mayweather, 50 Cent was able to walk away with one million in winnings. He proved, again, that his inner voice had a knack for betting when he scored $500,000 in winnings after placing a successful bet for the Giants in their NFC championship game against the 49ers. Clearly, his inner voice knows what it’s talking about.

John McCain

While John McCain hasn’t scored the large public payloads that these other celebrity gamblers have, he has shown that games of chance have a special place in his heart. In 2013, Senator McCain was caught playing Poker on his iPhone during a hearing discussing US intervention in Syria. Obviously, this was a very controversial and lead to many people questioning his interest in the crisis, making McCain a notorious celebrity gambler.

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