Gambling is an activity that’s loved by people from all areas of life and actors are no exception. Most of them, however, seem to love to keep a low profile when it comes to their favorite pastime. It’s almost certain that many of them use online real money casinos to gamble so that they can stay away from nosey paparazzi.
However, there are also some A-list actors who are proud of their gambling exploits. In this post, we’re going to present you with five Hollywood superstars who just love to gamble.
Jennifer Tilly
Jennifer Tilly is an actress by trade, but she’s also a professional poker player. The voice behind Family Guy’s Bonnie Swanson is a bracelet winner at World Series of Poker who’s got tournament winnings of over $1,000,000.
Her love for the game was sparked by her father who was a pro poker player as well. He was the one who gifted her the video game World Series of Poker, which made her obsessed with card games. Her passion for poker stayed with her even after her acting career kicked off.
Tilly’s first husband Sam Simon of the Simpsons fame was also a passionate poker player, and the same goes for her current partner Phil Laak.
Toby Maguire
It’s rumored that Player X from the 2017 movie Molly’s Game is actually Tobey Maguire in real life. Whether that’s true or not, it’s no secret that the Spider-Man star is a huge fan of gambling.
His game of choice is Texas Hold’em poker, in which he’s achieved considerable success in various tournaments. For instance, Maguire won Phil Helmout’s Poker Invitational tournament at Hollywood Park Casino in Los Angeles, cashing in just under $100,000.
Matt Damon
Here’s another actor whose favorite game is poker. Matt Damon’s poker story started during the filming of the 1998 movie Rounders. The film tells the tale of two friends who use their poker-playing knowledge to pay off loan sharks. Still in his 20s at the time of filming, Damon had limited knowledge of the game, which is why he hired an expert poker player as his tutor.
The man in question is legendary 10-time World Series of Poker (WSOP) winner Johnny Chan. Not only did he teach Damon how to play poker, but he made the actor fall in love with the game. Some 11 years after the release of Rounders, Damon took part in a WSOP event.
Ben Affleck
Same as his best friend Matt Damon, Ben Affleck too is a passionate poker player. Similarities don’t end there; he too gained poker skills after being under the tutelage of pro players. In Affleck’s case, it wasn’t one poker expert who taught him all the tricks of the game, but two of them – Amir Vahedi and Annie Duke.
What’s interesting is that Affleck’s love for card games doesn’t stop with poker. He’s also a huge fan of blackjack. At least that’s the impression we get from the fact that he was spotted playing this game in Vegas numerous times.
Ashton Kutcher
Back in 2013, Ashton Kutcher found himself in the midst of a huge controversy. It was revealed that the actor was a bet placer for Billy Walters’s betting syndicate. Although betting syndicates aren’t illegal in America, bookmakers and casinos do not like them. More often than not, those identified as members of a syndicate are banned by bookies from placing bets. That’s why they hire non-gamblers to do it for them.
And Kutcher was an ideal choice. Bookmakers thought he was a “dumb actor” – in his own words – but he was placing carefully selected wagers for the largest gambling organization in the US at the time. According to Kutcher, they cleared roughly $750,000 in under a month.
Charlie Sheen
It was 2006 when Charlie Sheen’s ex-wife Denise Richards revealed he was spending huge sums of money on betting. She claimed that his habit of placing $200,000 a week on sports bets was one of the key reasons that led to their divorce.
Sheen lost huge sums of money but also recorded some big wins. As per his own admission, he once placed a $1,000,000 bet on Manny Pacquiao beating Oscar De La Hoya in 2008. The reason he did it? He had a dream about the bout.
In an interview with the New York Times, Sheen stated that the Pacquiao bet was his final bet. If true, it means that he’s been staying away from sportsbooks and casinos for over 15 years now.
Honorable Mention: 50 Cent
Although he’s best known as a rapper, 50 Cent did act in more than two dozen movies and even produced a couple of them. In between rapping and acting, he also dipped his toes into sports betting.
He got into the spotlight in 2012 when he placed a $500,000 bet on the New York Giants winning the NFC Championship Game against the San Francisco 49ers. His team won in overtime and 50 Cent gave the winnings to his grandma.
