Do you love to play table games in person or collect the bonus spins when you play slots online? No matter what kind of gambling gets you going, you’re in good company! Many celebrities also like to gamble—especially when playing poker.
Is it easier to bluff and raise the stakes at the poker table if you’re a great actor? Maybe! That could explain why some of our most beloved actors are also great gamblers. Or maybe they really know the cards! Either way, if you’re a poker buff, you share a passion with some of the biggest names in Hollywood. Your favourite celebrities like Spider-Man’s Tobey Maguire, Shannon Elizabeth of American Pie, and horror flick star Jennifer Tilly dominate at poker tables and competitions alike.
Believe it or not, even sitcom family man Ray Romano of Everyone Loves Raymond is a regular at the World Series of Poker! These celebs’ poker prowess adds another dimension to their already charismatic personalities and glamorous lifestyles. Read on to learn more about these actors-turned-gamblers and the high-stakes spaces they occupy when they belly up to the green felt.
Ray Romano
Ray Romano may play Italian-American everyman on the hit TV show Everybody Loves Raymond, but since the show ended, he’s played a skilled card player in real life. Outside of acting, he has a passion for poker and has achieved significant success—including an especially notable victory in the 2011 World Series of Poker Main Event, where he won $75,000!
Romano regularly appears at major tournaments despite being a famous Hollywood name. His love of the game endures while playing in the 2023 World Series of Poker Super Bounty No-Limit Hold ’em event. Just like he connects with his audiences through comedy, Ray Romano connects with poker through a genuine love of the game, so you’re sure to see him at the table again soon!
Shannon Elizabeth
Though best known for her sex-symbol roles in early-aughts classics like the American Pie series and Scary Movie, Shannon Elizabeth has also crafted a name for herself in the gambling world.
She called poker her “second career” in 2006 and visited Las Vegas on the regular to play against top opponents. While she may not play as often these days—her last tournament win was in 2013—she remains a popular name in celebrity poker.
During the peak of her career, Elizabeth played in 2005’s Main Event at the World Series of Poker and won a special tournament for Caesars Palace’s new game room in 2006. There, she bested 83 fellow celebrities and poker professionals to pocket a cool $55,000 in winnings. In 2007, she made it to the semi-finals of NBC’s National Heads-Up Poker Championship.
Tobey Maguire
Spider-Man was at the centre of some of Hollywood’s most clandestine high-stakes games—the very same gathering of big names that inspired the movie and book Molly’s Game. In the mid to late 2000s, Tobey Maguire brought together players like Leonardo DiCaprio, Matt Damon, Ben Affleck, and other industry names to compete in underground L.A. poker games.
These high rollers gathered at the Beverly Hills Four Seasons and the Viper Room, where they wagered, won, and lost big. Unfortunately, the fun came to an end when Maguire and others ended up as defendants in a court case concerning the private games. Ponzi schemes, dirty money, slighted investors, and more all come together in this wild and true tale of Tobey Maguire’s foray off the silver screen and onto the gaming floor.
Jennifer Tilly
Raised on rural Texada Island and in Langford on Vancouver Island, British Columbia, Jennifer Tilly is best known for her roles in Bride of Chucky (and its sequels) as well as Liar Liar alongside fellow Canadian-American Jim Carrey.
She’s also earned her place as a celebrity poker legend and is the proud owner of a coveted World Series of Poker bracelet. Tilly captivates both on screen and at the table, where she has showcased a knack for reading opponents.
Her accolades include a $158,335 prize in 2005 for the World Series of Poker $1,000 Ladies’ No Limit Hold ’em; CardPlayer’s 2005 Best Celebrity Card Player of the Year, World Poker Tournament 2005 win of $25,000; and 2010’s WPT Bellagio Cup 5K win of $120,000-plus.
Jason Alexander
You may know him as George Constanza from Seinfeld, but in the real world, Jason Alexander is much more than just a short, stocky, slow-witted balding man. He’s a bonafide poker player!
Alexander has played in numerous tournaments, including the World Series of Poker. Despite having yet to win a bracelet, Alexander perseveres at the poker table and often for a good cause. In addition to playing in high-profile events and winning on season eight of Bravo’s Celebrity Poker Showdown tournament, Alexander often donates his jackpots to those in need.
During his time on Bravo, he won $500,000—all of which went to the United Way of Greater New Orleans. He has also played in Ante Up for Africa. Giving away all your winnings seems like the opposite of what George Constanza would do, but that goes to show you what a skilled player and actor Mr. Alexander is.
Conclusion
Competition, charity, and even clandestine card games collide in the world of celebrity poker. Stars like Tobey Maguire, Jason Alexander, and Ray Romano have all made headlines with their films and poker power alike. These stars’ involvement in poker tournaments and events underscores the competitive draw and passion that all kinds of people hold for the game.
Whether they use their wins for charity or personal gain, these celebs have proved they are in it to win it—whether it’s their next Oscar or poker championship. It’s not all glitz and glam, though, as high rollers like Tobey Maguire found out after becoming embroiled in controversy concerning his private, Hollywood elite games. For him, the high-stakes drama of TV and film became real life!
Nevertheless, these celebrities know that poker transcends the exclusivity of the entertainment industry. Competition, charity, and intrigue abound when celebrities step into the gambling space. Continue to watch these names captivating the poker world to see what’s next, whether it be a big win, charitable gift, or breaking scandal.
