Hollywood celebrities live for the thrill—whether it’s on-screen action or high-stakes gambling. Some of the biggest names in the industry have tested their luck at casinos, with jaw-dropping wins and, sometimes, devastating losses. Here’s a look at some of the most legendary casino wins in Hollywood history.
Ben Affleck – The Blackjack King
Oscar-winning actor Ben Affleck isn’t just a talented filmmaker; he’s also a skilled blackjack player. In 2014, he was reportedly banned from playing blackjack at the Hard Rock Casino in Las Vegas after winning too much. Affleck allegedly mastered card counting, a legal but frowned-upon strategy, and took home hundreds of thousands in winnings before the casino asked him to stop playing.
Charlie Sheen – The Big Roller
Known for his extravagant lifestyle, Charlie Sheen was once a high-stakes gambler, reportedly betting $200,000 per week at the height of his career. While specific details of his wins remain unclear, Sheen admitted to losing millions in gambling, proving that even celebrities aren’t immune to the risks of the casino floor.
Dana White – Casino Enemy No. 1
UFC president Dana White is one of the most successful celebrity gamblers. He has reportedly won millions at Las Vegas casinos, particularly in blackjack. However, his repeated wins led to multiple casinos banning him from playing at their tables. White has confirmed in interviews that some casinos even refused to let him place bets because he was too good at the game.
Tobey Maguire – Underground Poker Champ
Spider-Man star Tobey Maguire was a major player in the high-stakes poker scene, participating in exclusive underground games with other celebrities and wealthy businessmen. He was rumored to have won millions, but his name became infamous when his involvement in an illegal poker ring was exposed in 2011.
Paris Hilton – A Lucky Night in Vegas
Paris Hilton once walked into a Las Vegas casino and walked out with $30,000 in winnings—on her first try. She credited her luck to wearing a lucky dress, proving that sometimes, fortune favors the bold (and fashionable).
