Hollywood is known for its glamour and indulgence. Many actors and actresses have become interested in high-stakes living in the casino world, and many celebrities have been known to frequent some of the world’s top casinos. We have conducted a study and explored the casino gambling habits of actors and actresses, compiling a list of those who have embraced the world of chips and cards. Our study considered casino visits, gambling preferences, winnings, and notable appearances in poker tournaments.
| Celebrity | Game of Choice | Notable Wins | Estimated Winnings | Estimated Gambling Losses | Casino Hotspots |
| Ben Affleck | Blackjack | 2004 California State Poker Championship | $800,000+ | Banned from Hard Rock LV | Las Vegas, Monte Carlo |
| Tobey Maguire | Poker | High-stakes poker games | $10 million+ | Involved in poker scandal | Las Vegas, Private games |
| Charlie Sheen | Sports betting | 2008 Manny Pacquiao vs. Oscar De La Hoya boxing match | $1 million+ | Millions in bets | Las Vegas |
| Matt Damon | Poker | Participation in World Series of Poker | $100,000+ | Unknown | Worldwide Poker Tournaments |
| Pamela Anderson | Poker | Unknown | $1 million+ | $250,000 in a poker game | Las Vegas |
| Ray Romano | Poker | Frequent World Series of Poker contestant | $50,000+ | Unknown | Charity Poker Events |
| Jennifer Tilly | Poker | World Series of Poker Bracelet (2005) | $1 million+ | Unknown | Poker Tournaments worldwide |
| George Clooney | Poker | Unknown | $1 million+ | Las Ramblas Casino Project | Las Vegas, Monte Carlo |
| Brad Pitt | Poker, Blackjack | Unknown | $1 million+ | Unknown | Monte Carlo, Las Vegas |
| Paris Hilton | Poker, Blackjack | Unknown | $1 million+ | Unknown | Las Vegas, Monte Carlo |
Ben Affleck
More than just an actor, Ben Affleck has made a name for himself at the blackjack tables. Known for winning the 2004 California State Poker Championship, Affleck’s expertise in blackjack once led to him being banned from the Hard Rock Casino in Las Vegas for card counting. His gambling ventures have taken him to renowned Las Vegas and Monte Carlo casinos, where he remains a prominent figure in the gaming world.
Tobey Maguire
Famed for playing Spider-Man, Tobey Maguire is equally renowned in high-stakes poker circles. His love for poker has involved him in elite private games, and he was part of a well-known underground poker scandal. Maguire regularly plays in exclusive, high-stakes poker matches, often alongside other Hollywood heavyweights.
Charlie Sheen
Charlie Sheen’s larger-than-life persona extends to his gambling habits, particularly his passion for sports betting. Notably, Sheen placed a million-dollar bet on the 2008 Pacquiao vs. De La Hoya boxing match. Known for wagering millions on sports events, Las Vegas remains his preferred playground for high-stakes action.
Matt Damon
Matt Damon developed a deep interest in poker during the filming of Rounders. He has since participated in the prestigious World Series of Poker and other major tournaments globally. With a competitive spirit, Damon regularly attends poker events worldwide, becoming a recognized player in the casino scene.
Pamela Anderson
Pamela Anderson’s poker-playing skills have been showcased in Las Vegas, where she has reportedly won over a million dollars at the tables. Known for her glamorous image, Anderson’s love for poker is so strong that it even influenced her personal life, as she has attributed one of her marriages to a poker game.
Ray Romano
Beloved comedian Ray Romano has become a familiar face in the poker world. He frequently competes in the World Series of Poker and participates in charity poker events. Romano’s approachable personality and enthusiasm for the game have endeared him to fans and fellow players in Hollywood and beyond.
Jennifer Tilly
Jennifer Tilly is a rare combination of Hollywood actress and professional poker player. She made waves in poker by winning a World Series of Poker bracelet in 2005. Tilly’s success in acting and poker has earned her admiration from both communities, solidifying her reputation as a skilled player on the global poker circuit.
George Clooney
George Clooney’s love for poker reflects his stylish, debonair image. Though best known as an actor, Clooney has also been involved in the casino industry, most notably with the Las Ramblas project in Las Vegas. His poker games often occur in high-end casino hubs like Monte Carlo, where he’s a familiar face.
Brad Pitt
Brad Pitt’s interest in casino games was piqued during the filming of Ocean’s Eleven. Since then, he’s become known for his quiet but sophisticated approach to poker and blackjack. Pitt occasionally visits luxury casinos in Las Vegas and Monte Carlo, where he enjoys gambling with the same calm demeanor seen in his films.
Paris Hilton
Paris Hilton, the epitome of a glamorous socialite, brings her flair to the casino world. She’s often seen at high-stakes poker and blackjack tables in Las Vegas and Monte Carlo, blending her passion for gambling with her jet-set lifestyle. Hilton’s frequent appearances in luxury casinos keep her at the forefront of the celebrity gambling scene.