Celebrity Gamblers: Famous Stars Who Love Gambling
Last Updated on June 25, 2025 by Mary Henderson
What really goes down when the famous hit the casino floor? I was lucky to see it up close back in the day, when I used to work as a croupier. I mean – unfiltered crazy wins and epic losses that only a croupier can spill.
Now, as a digital publisher, I’m here to dish out the real stories of celebrity gamblers like you’ve never seen before. I’m talking about famous people who can throw down a fortune on a whim while keeping it cool.
Ready for some juicy insider tales? Let’s see the top 10 celebrity gamblers.
#1 Ben Affleck: From Red Carpets to Blackjack Tables
Here’s the scoop on our boy Ben. Not only does he rock the screen as a filmmaker and actor, but he’s also a blackjack pro and a gambling celebrity.
Besides the movie magic, Ben Affleck has some serious blackjack skills. His passion hit the headlines when he got booted from the Hard Rock Casino in Vegas. Guess why?! Card counting. Yep, card counting is not illegal, but casinos aren’t having it, so it was a “no”.
Ben has got the moves. He’s landed some big wins at major blackjack tournaments, like a pro that he is. But what really blew my mind is his mastery of the game. He’s dedicated to learning tricks and tactics that put him way ahead of the curve. One of the reasons why he stands out among other star gamblers.
#2 Matt Damon and His Passion for Poker – Who Knew?
Yeah, that very Matt Damon, Ben Affleck’s best friend. Dude’s got a thing for high-stakes poker and is also a famous gambler. It all started with the “Rounders” movie that sparked his interest in the game. Ever since, Damon has been all about poker, becoming a regular at WSOP (World Series of Poker).
Trust me, I’ve seen a ton of sharks, and Damon’s vibe is real. He literally feels the thrill and challenge. Plus, he’s a well-respected player and enjoys the company that comes with playing poker.
#3 Charles Barkley’s Love for High Stakes
You know exactly who I’m talking about. Yes, the NBA star. Can you picture him dropping serious cash on his new passion? Well, the NBA superstar admitted to spending millions on gambling, and no regrets.
I mean, come on, he’s really got that charm that would make every bet a thrill. Barkley enjoys everything from poker to blackjack and sports betting. The rush is like no other for him. And it isn’t just about money (obviously). It’s about unfiltered pleasure.
Who are we to fault the guy for enjoying something that brings him such an epic moment?
#4 Tobey Maguire: Spider-Man’s Secret Side
More like Poker Man, don’t you think?
Our friendly Spider-Man is not busy just swinging through skyscrapers; he’s also into poker and a celebrity gambler. And not just a connoisseur, but a pro. He’s a total ace.
Word on the street is that he might even have gotten linked to that underground club for celebs and wealthy people who drop some serious cash in poker. True? It may be. What I know for sure is that Tobey has a competitive edge and a very sharp mind that makes him a real beast at high-stakes games.
Is it another secret superpower that we didn’t know about Spider-Man? Well, this personality trait surely adds a cool air to his star image.
#5 Pamela Anderson: Poker’s Unexpected Queen?
Did you know Pamela Anderson isn’t just about Baywatch? Well, besides being an actress and model, she’s also a pretty serious female gambler. A devoted celebrity gambler, if you may.
Pamela behaves like a pro on the casino floor, not just lounging around as you might have thought. Nope, she jumps right into action. Hitting up celeb tournaments regularly has always been a thing, where she plays for charity.
If you’re into star gambling, Pamela’s your gal!
#6 Floyd Mayweather’s Sports Betting World
Floyd “Money” Mayweather in action off the ring.
He’s not only the champ at throwing punches but also a total boss at sports betting. Guy’s living a luxe life and doesn’t hesitate to show off his epic betting slips on social media. I mean, he’s dropping huge amounts, like it’s no big deal at all.
With all the experience he’s got over the years, it’s safe to say he’s become a figure in the sports betting scene. And it’s hard not to take notice.
#7 Tiger Woods: From Golf Greens to Blackjack
I bet you know about Tiger Woods as the golf genius. But did you know he loves blackjack almost as much and is also a gambling celebrity?
He’s been seen in Vegas dropping big bucks at blackjack tables. At times, perfecting his swings, and at others, strategizing his next card move, he’s all about precision.
Combining the game on the green with high-stakes gambling? Woods is your guy.
#8 Ray Romano and His Way Around Cards
Yep, the hilarious guy behind “ Everybody Loves Raymond” not only knows how to crack jokes on screen. He’s all about poker off-camera.
Romano’s been spotted at major poker events like WSOP, where he shows his mix of card skills and sharp wit, so peculiar of comedians (I meant the latter). You’ll hardly find a poker game without Romano’s appearance.
#9 Shannon Elizabeth: Poker Shark in the Spotlight
You remember Shannon Elizabeth from “American Pie”? Did you know she’s also a professional poker player and a celebrity gambler? Someone’s got a brand-new full-on second career you might not even know about.
Tell you more, she’s not in for kicks. Shannon hits up major tournaments. So next time you see her on screen, remember that she’s not just a pretty face but also a poker pro with mad respect among players.
#10 Jennifer Tilly: Oscar-Nominated Star Turned Poker Pro
This lady’s got a poker face.
Once nominated for an Academy Award, Jennifer Tilly is now a professional poker player. She even won a WSOP bracelet.
Her casual interest in the game developed gradually into something serious, and her accomplishments along the way show just how good she is at this game, far away from the showbiz.
Hope you enjoyed this teeny-tiny behind-the-scenes. Till next time!
This article is written by Mary, a seasoned professional with a rich background as a casino croupier now transitioned into a digital publisher with a keen focus on the online casino scene. With years of firsthand experience on the casino floor, Mary offers her unique perspective to the digital world of gambling.
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