I've spent over 20 years inside the betting industry. I'll guide you to avoid the hype, ignore the noise, and steer clear of the common pitfalls that catch out everyday punters.
Casinos have long been a playground for the rich and famous. Over the last five years, a surprising number of A-listers, sports legends, and global entertainers have made headlines not for premieres or press tours, but for their high-stakes escapades at the tables.
Whether they’re chasing adrenaline, testing their skill, or simply embracing the spectacle of Las Vegas and Monte Carlo, these celebrities prove that the thrill of the gamble transcends industries.
Below, we spotlight the most notable celebrity casino regulars and the stories that cemented their reputations.
1. Ben Affleck: Hollywood’s Blackjack Pro
Ben Affleck has become almost as synonymous with blackjack as he is with blockbuster films. His skill at the tables, particularly card counting, reportedly led to him being asked to leave the Hard Rock Casino in Las Vegas for being “too good.”
Known for winning big and taking the game seriously, Affleck has appeared at high-roller tables for years. He even won the California State Poker Championship in the early 2000s, proving his card-play talents aren’t limited to blackjack. For Affleck, casinos offer both competition and the thrill of outsmarting the house.
2. Matt Damon: Poker Enthusiast On and Off Screen
Matt Damon’s role in Rounders wasn’t just cinematic; it sparked a lasting interest in poker.
Over the past five years, he’s been spotted at major poker tournaments, charity events and even the World Series of Poker. Calm, sharp, and strategic, Damon brings the same discipline to the felt that he brings to acting, often competing alongside professional players. His love of the game has clearly outlived the movie that ignited it.
3. Drake: Hip-Hop’s High Roller
If there’s a celebrity who defines the modern high-roller lifestyle, it’s Drake.
The rapper regularly places eye-watering wagers, livestreams roulette sessions, and has partnered with a cryptocurrency casino platform.
Recent years saw him:
- lose around $500k betting on his hometown NBA team
- wager over $1 million on the Kansas City Chiefs due to “not betting against the Swifties”
- and celebrate massive roulette and sports betting wins with millions of followers watching
Whether it’s online or in a luxury casino suite, Drake’s gambling is always high-stakes and highly public.
4. Floyd Mayweather: The King of Big Bets
Floyd “Money” Mayweather’s nickname speaks for itself.
A staple in Las Vegas casinos, Mayweather is renowned for turning sports wagers into six- and seven-figure payouts. He’s posted countless betting slips featuring million-dollar wins, though losses are kept far quieter.
From dropping $100,000 on a single blackjack hand to casually wagering half a million on football, Mayweather treats the casino floor like another arena where he expects to dominate.
5. Leonardo DiCaprio: A Discreet VIP Player
Leonardo DiCaprio may avoid the spotlight when gambling, but he’s very much a regular.
Preferring private rooms and exclusive VIP salons in Vegas and Monaco, DiCaprio is known for joining elite high-stakes poker games among Hollywood’s inner circle.
While he keeps his play low-key, he has been linked to several real-life celebrity poker circles, a quieter but equally serious presence at the tables.
6. Michael Jordan: The Legend With a Legendary Gambling Habit
Michael Jordan’s competitive fire doesn’t switch off when he leaves the court.
His gambling stories, from casino visits during NBA playoff runs to million-dollar golf bets, have become part of his mythos. Reports have claimed multimillion-dollar casino losses in a single night and high-stakes sessions throughout the 1990s and beyond.
Even today, anecdotes surface about Jordan’s big-money bets, showing that his drive to outplay opponents never faded.
7. Charles Barkley: Candid About His Casino Losses
Charles Barkley has never hidden his gambling history, even the painful parts.
The Hall-of-Famer once admitted to losing more than $25 million at casinos over the course of his life, including a notorious $2.5 million loss in a single Las Vegas weekend.
In recent years, Barkley says he’s brought more moderation to his betting, but he still enjoys the casino atmosphere. His openness and sense of humour about his past losses, have made him something of a folk hero among Vegas regulars.
8. Neymar Jr: Football Superstar Turned Poker Addict
Neymar Jr.’s passion for poker is well known, and over the last five years it has flourished.
He made his WSOP debut in 2022 and frequently appears at high-profile tournaments and online games.
His most infamous moment came during a livestreamed session where he lost around €1 million in under an hour, laughing throughout. The loss barely fazed him, and he has even stated he plans to pursue poker professionally after retiring from football.
9. Tiger Woods: A Vegas High-Stakes Regular
At the height of his fame, Tiger Woods was a major presence in Las Vegas casinos.
He reportedly wagered up to $25,000 per hand at exclusive blackjack tables and was granted a $1 million betting limit at MGM’s elite Mansion salon. Tales of winning, and losing, seven-figure sums in a night became part of Tiger’s Vegas lore.
In more recent years, Woods has kept his gambling quieter, but stories from the 2000s continue to shape his casino reputation.
10. Bruno Mars: The Rumoured Big Spender
Bruno Mars’ long Vegas residency has fuelled rumours that he’s a major casino player.
In 2024, viral reports falsely claimed he had racked up $50 million in debt, rumours quickly refuted by both Mars and MGM Resorts. His playful response only amplified speculation about his casino habits, but whether he gambles heavily or not, his long-running presence in Vegas keeps him tied to its gaming culture.
Conclusion
Some of the world’s biggest celebrities are also regulars at high-stakes casinos. From Ben Affleck’s blackjack mastery and Drake’s million-dollar wagers to Neymar’s poker obsession and Floyd Mayweather’s huge sports bets, these stars bring their wealth to the tables. Their adventures reveal how gambling appeals to actors, athletes and musicians alike, often with spectacular wins, staggering losses and unforgettable stories.
Sources:
South China Morning Post – Celebrities who love gambling (Feb 22, 2025)
Hollywood.com – Celebrity Betting & Casino Sightings (Mar 11, 2025)
KTVZ – 10 of the biggest celebrity gamblers (Sept 25, 2024)
ESPN – Neymar’s WSOP debut and poker ambitions (Jun 13, 2022)
People – Bruno Mars on gambling debt rumors (Jul 15, 2025)
- GamesHub – Neymar’s €1M online poker loss (Sept 11, 2025)
