Risk and reward have always gone hand in hand in the world of fame. From bold career moves to lavish lifestyle choices, celebrities are no strangers to gambling, both metaphorically and literally. As online platforms, casinos, and sports betting apps have grown more accessible, many stars have embraced gambling in its various forms.
Whether it’s poker nights in private clubs, multi-million-dollar sports bets, or spinning the roulette wheel under Vegas lights, celebrity gambling habits intrigue fans and critics alike. The mix of fame, fortune, and high-stakes wagers makes their stories all the more compelling.
This article takes a closer look at famous celebrities who gamble, the games they play, the wins they chase, and the risks they’re willing to take.
Top 12 Famous Celebrities Who Gamble
From sports legends and Hollywood icons to music moguls, many celebrities find the thrill of gambling irresistible.
Some keep it casual, while others are known for making bold, high-stakes bets. This section profiles 12 famous personalities across different industries and continents, each with a notable connection to gambling culture.
Top 12 Famous Celebrities Who Gamble & Their Casino Hotspots:
| Sr. No | Celebrity | Fav Game | Casino Hotspots |
|---|---|---|---|
| 1 | Bruno Mars | Blackjack, Rumored Slots | Las Vegas |
| 2 | Drake | Sports Betting | Online via Stake |
| 3 | Charles Barkley | Blackjack | Las Vegas |
| 4 | Michael Jordan | Golf Bets, Craps | Las Vegas |
| 5 | Tiger Woods | High-Stakes Table Games | Las Vegas |
| 6 | Jennifer Tilly | Poker | Worldwide Tournaments |
| 7 | Ben Affleck | Blackjack, Poker | Las Vegas, Monte Carlo |
| 8 | Matt Damon | Poker | Global Poker Events |
| 9 | Tobey Maguire | Poker | Hollywood, Private Games |
| 10 | 50 Cent | Sports Betting, Blackjack | Las Vegas |
| 11 | Ray Romano | Poker | Charity Tournaments |
| 12 | Charlie Sheen | Sports Betting | Las Vegas |
Each of the following profiles highlights how these celebrities gamble, where they play, and what makes their betting habits noteworthy.
1. Bruno Mars
Bruno Mars, the Grammy-winning performer, spent eight years as a resident headliner in Las Vegas, a city synonymous with high-stakes gambling.
Known for his polished stage presence, his off-stage habits caught attention in 2024 due to explosive rumors about a $50 million gambling debt.
While Mars and MGM have denied these claims, his name continues to appear in gambling discussions.
His presence in Las Vegas and the rise of online speculation make him one of the most talked-about entertainers linked to casino culture.
2. Drake
Drake is as bold in betting as he is on stage. Since 2022, he’s been in a high-profile partnership with crypto-gambling platform Stake, through which he showcases his massive sports bets on social media, from UFC to NBA playoffs.
In 2024, he staked $1.15 million on the Super Bowl, aligning with Taylor Swift fans.
Not all bets land in his favor, and some even suggest that Drake is cursed; losses like a $2 million UFC wager prove that even megastars face tough odds. Yet, the attention fuels both his brand and Stake’s reach.
3. Charles Barkley
NBA Hall of Famer Charles Barkley has never shied away from talking about his gambling. Known for his charismatic honesty, Barkley once revealed losing $2.5 million in a single blackjack session and claims to have lost up to $25 million over the years.
Despite such staggering losses, Barkley maintains that gambling is a personal form of entertainment.
His long-standing presence at Las Vegas tables reflects his enduring belief in taking risks, both on and off the court, a mindset common among celebrities who immerse themselves in different casino games.
4. Michael Jordan
Michael Jordan’s competitive fire extends far beyond basketball. The six-time NBA champion is famous for his intense love of betting, from golfing wagers with friends to alleged multimillion-dollar casino losses that surfaced throughout his career.
His gambling habits were even spotlighted in Netflix’s The Last Dance. Though always controversial, Jordan frames gambling as part of his personal competitive drive, a natural extension of the mindset that made him a legend.
5. Tiger Woods
Tiger Woods, one of golf’s greatest figures, has long been linked to casino gaming. As a young athlete, Woods was reportedly frequenting VIP casino rooms in Las Vegas, often alongside fellow high rollers like Michael Jordan and Charles Barkley.
Though he’s kept details private, insiders say Woods enjoys blackjack and poker. Games that are particularly attractive due to their odds and the skill involved show why understanding how gambling odds work is crucial even for the elite.
6. Jennifer Tilly
Jennifer Tilly is a rare celebrity who turned gambling into a legitimate second career. The Oscar-nominated actress won a World Series of Poker bracelet in 2005 and remains a recognizable name in elite poker tournaments worldwide.
Beyond her film roles, Tilly is an ambassador for women in poker. Inducted into the Women in Poker Hall of Fame, she has earned the respect of fans and professionals alike for her skill and commitment to the game.
7. Ben Affleck
Ben Affleck is as methodical at the card table as he is behind the camera. The Hollywood star famously won the 2004 California State Poker Championship and became so skilled at blackjack that the Hard Rock Casino allegedly banned him for card counting.
While such behavior isn’t illegal, it often toes the line of regulation depending on the location, which raises questions about legal gambling countries and how laws differ across borders.
Affleck’s love of strategy games fits his analytical personality. He continues to be seen at major poker tournaments, often with longtime friend Matt Damon, bringing his signature focus to every hand he plays.
8. Matt Damon
Matt Damon’s relationship with poker began during the filming of Rounders, a cult classic among gambling enthusiasts. Since then, he’s played in major events like the World Series of Poker and numerous charity tournaments.
He’s often seen beside Affleck at high-stakes tables, and his strategic approach to the game has made him a respected amateur in the poker community. Damon credits the game for helping him focus and unwind.
9. Tobey Maguire
Tobey Maguire gained notoriety in poker circles for his role in exclusive, underground games that inspired Molly’s Game. The “Spider-Man” star was reportedly one of the sharpest and toughest players at the table.
He participated in high-stakes games with fellow celebrities and financiers, earning millions in winnings. Though no longer as public about his play, Maguire remains a respected figure among serious poker fans.
10. 50 Cent
Rapper and entrepreneur 50 Cent is no stranger to risk. His gambling history includes betting $500,000 on an NFL championship game and reportedly putting down $1.6 million on a Floyd Mayweather fight, bets that show his comfort with big numbers.
In 2015, he launched his own blackjack game on Facebook, blending music, business, and casino culture.
Known for his bravado, 50 Cent’s gambling ventures mirror his fearless public persona.
11. Ray Romano
Ray Romano brings his comedic charm to the poker table. A regular participant in World Series of Poker events and charity tournaments, Romano is deeply passionate about the game and treats it as more than just a hobby.
Despite not being a professional, he holds his own against seasoned players. Poker, for Romano, offers a relaxed yet mentally engaging escape from his showbiz career, one he’s proudly shared with fans for years.
12. Charlie Sheen
Charlie Sheen’s gambling habits have often made headlines, much like his acting career and personal life. He’s known for his love of high-stakes sports betting, allegedly wagering millions on events like major boxing matches and NFL games.
Such high-risk gambling behavior can lead to lasting legal and financial issues. In some cases, it may even impact your mortgage eligibility or loan credibility based on spending habits.
Are Celebrities Who Are Gambling Winning?
Celebrity gamblers often have fortunes to back their bets, but winning isn’t guaranteed, and for some, gambling becomes more than just a game.
While stars like Ben Affleck and Jennifer Tilly have seen success at poker tables, others like Charles Barkley and Michael Jordan have faced major losses; Barkley once estimated losing $25 million.
Tilly, however, turned poker into a second career, proving that discipline and skill matter. For some, money isn’t the issue; addiction is. Gladys Knight sought help for compulsive gambling, while Charlie Sheen and others have also struggled, risking personal and professional stability.
Overall, celebrity gambling results are mixed. Winning often depends on strategy and moderation, but the financial, emotional, and reputational risks are very real, even for the rich and famous.
Why Does Celebrity Gambling Catch Media Attention
When celebrities place massive bets, it’s often about more than just the money. It’s about creating a spectacle.
High-stakes gambling has become part of how some stars shape their public image, with bold wagers drawing intense media attention and turning private games into public entertainment.
The mix of fame, wealth, and risk fuels headlines and sparks both admiration and criticism.
Take Drake’s $1.15 million Super Bowl bet, tied to Taylor Swift fandom, or Mattress Mack’s record-breaking $75 million win on the Astros.
Even Floyd Mayweather made headlines attempting to bet on himself during his 2017 fight with Conor McGregor, a move blocked by regulators but still widely reported.
These moments show how celebrity gambling transcends the casino floor and becomes a global talking point, and often take place in some of the richest casinos in the world, where ultra-high-stakes play is the norm.
Conclusion: Bruno Mars Leads The Famous Celebrities Who Gamble
From poker tables to sportsbook apps, celebrities from all walks of fame have embraced gambling in their own ways. While some treat it as a casual pastime, others approach it with professional intensity or reckless abandon.
These gambling habits reflect a larger truth about celebrity culture: the line between entertainment and excess is often thin. For many stars, the thrill of risk-taking doesn’t end with their careers; it spills into their personal lives with both exhilarating wins and painful losses.
Whether it’s a million-dollar bet or a charity poker night, gambling has become another arena where fame, fortune, and risk collide. These are the wagers of famous celebrities who gamble.
FAQs
Ben Affleck, Matt Damon, Tobey Maguire, and Jennifer Tilly are well-known poker enthusiasts. They’ve participated in high-stakes games and tournaments, with Tilly even winning a World Series of Poker bracelet.
Michael Jordan’s betting habits sparked investigations in the ’90s, Ben Affleck was banned from a casino for card counting, and Tobey Maguire was involved in a high-profile underground poker scandal.
Drake regularly places and publicizes massive sports wagers. Charlie Sheen and 50 Cent are also known for bold bets on major sporting events.
Absolutely. Jennifer Tilly is a professional poker player, and stars like Paris Hilton, Pamela Anderson, Shannon Elizabeth, and Lady Gaga have also been associated with gambling, particularly in poker and slot games.
Drake’s bets range from million-dollar wins to multi-million-dollar losses. Charles Barkley admitted to losing up to $25 million. Jim “Mattress Mack” McIngvale made history with a $75 million sports betting win.
