13 Celebrities Who Love Playing and Winning at Blackjack

We're sure you've guessed correctly – the first celebrity on the list has famously been connected to gambling ever since he first graced the movie screen. Benjamin Geza Affleck is perhaps the most publicly scrutinized celebrity blackjack player — and for good reason. Way back in 2014, Affleck was reportedly banned from playing blackjack at the Hard Rock Hotel and Casino in Las Vegas after casino security identified him as an "advantaged player" - a polite term for someone using legal card-counting strategies to gain an edge. Ben Affleck has never denied his interest in blackjack and, in interviews, has admitted to reading up on basic strategy and card counting.

His sharp memory and methodical approach to the game allowed him to win large sums, including a reported $800,000 haul in a single session at the Hard Rock. His passion for blackjack makes him not just a celebrity fan, but a serious student of the game — one who made casinos take notice.

Famous for: Winning two Academy Awards and two BAFTA Awards for Good Will Hunting and Argo; famous for playing Batman and, more recently, The Accountant

Amazing gambling facts: He won the California State Poker championship in 2004 and took home the first prize of over $356K. He was also one of the celebrities known for taking part in poker hostess Molly Bloom's infamous poker events in the 2000s.

Dana Frederick White, Jr., the president of the Ultimate Fighting Championship and a major personality in his own right in the sports world, is also one of the most successful – not to mention fearless - blackjack players among celebrities. He is known for placing six-figure bets at high-limit tables, and he has made headlines over the years for his blackjack prowess.

Dana White often plays for hours, betting tens of thousands of dollars per hand, and according to some reports, has taken home millions from Las Vegas casinos. At one time, the Palms Casino in Las Vegas reportedly banned him from playing blackjack because of his repeated large wins - including one streak where he won nearly $7 or $8 million in a single night. Despite his larger-than-life personality, White insists he takes blackjack seriously, and that is why he often plays with a disciplined strategy.

Famous for: Making the UFC a global powerhouse from its humble beginnings; he also famously co-founded the Power Slap League, a slap fighting event.

Amazing gambling facts: Dana White has been reportedly banned from blackjack tables in Las Vegas, and plays for high-stakes of at least $75K per hand. Most recently, he has won $1.2 million while playing blackjack for $300K a hand at the Fontainebleau in Vegas.

While the Don Johnson we all know may not be this Don Johnson – this Don Johnson is the casino executive and horse racing aficionado, not the "Miami Vice" star - earned celebrity status in gambling circles for famously beating Atlantic City casinos out of nearly $15 million in 2011.

Using a combination of negotiated rules, high-stakes play, and expert strategy (though surprisingly, not card counting), Don Johnson was able to turn the tables in his favor. His calculated moves, including getting casinos to offer favorable rules like re-splitting aces and 20% cashback on losses, helped him carve out a massive win streak. During a 12-hour session at the Tropicana, Don Johnson won $1.2 million. Thanks to even more favorable conditions, Johnson ultimately gained the edge over Tropicana for almost $6 million, Caesars for $4 million, and Borgata for $5 million - netting around $15.1 million in total. Though not formally banned from Tropicana or Borgata, both casinos changed the terms to prevent further play under those rules. Caesars, meanwhile, banned him outright. While not a household name outside gambling circles, Johnson's story is legendary among blackjack insiders and has inspired countless players.

Famous for: Being a former casino and horse racing executive and professional blackjack player.

Amazing gambling facts: He beat the casinos in Atlantic City and took home over $15 million in 2011

Eldrick Tont Woods, more commonly known as Tiger Woods, the golf legend, is known for his calm under pressure - a quality that also serves him well at the blackjack table. Woods has been spotted at high-limit blackjack rooms in Las Vegas on numerous occasions, particularly during the early 2000s.

He reportedly favored the exclusive rooms at MGM Grand, where he would often play at tables with limits as high as $25,000 per hand. Though Tiger is more private than other celebrity gamblers, like his buddies Charles Barkley and Michael Jordan, stories from casino insiders suggest he played frequently during his heyday. For instance, he reportedly played for a casino as a VIP with over a million-dollar line of credit. While there are no public records of massive wins, his consistency and love for the game have made him a quiet staple of the high-roller blackjack scene.

Famous for: Being one of the most medaled golfers of all time; he holds many golfing records and is an inductee in the World Golf Hall of Fame.

Amazing gambling facts: Rumors abound that he once staked $4 million in one night, and he is allegedly part of a VIP group in casinos which offers more than a million in credit.

NBA legend Charles Wade Barkley is no stranger to the casino floor. Known for his big personality and even bigger bets, Barkley has long been open about his gambling - including his time at the blackjack table. In interviews, he's spoken about both winning and losing millions in various casinos.

In one famous story, Barkley claimed he once won $700,000 in a single night playing blackjack and he is said to have lost a total of $10 million while gambling. But while he admits that gambling has cost him millions over the years, Barkley also says he has no regrets - it's all part of the experience. Despite a mixed record, his love of blackjack remains strong, and he continues to be a regular at casinos across the US. He knows that he eventually has to stop and it's a bad habit, but until then, he'll enjoy doing it.

Famous for: Playing for 16 seasons for the NBA; an 11-time NBA All Star and NBA Most Valuable Player for 1993; he is now a sports analyst for television.

Amazing gambling facts: He once lost $2.5 million in just six hours of playing blackjack, but he also won $700,000 from blackjack and sports betting.

Matthew Paige Damon, known more popularly as Matt Damon, Ben Affleck's longtime friend and fellow actor, also developed a taste for blackjack while preparing for the film Rounders, although that film focused on poker. However, during training and exposure to gambling culture, Damon became intrigued by blackjack strategy and has since been seen at various casinos playing the game.

While he doesn't have the same notoriety at the tables as his friend Ben Affleck or Dana White, Damon's approach to the game reflects a thoughtful interest rather than a casual pastime. He's been known to join charity blackjack events and play at VIP tables alongside his Hollywood peers, indicating a level of comfort and familiarity with the game.

Famous for: Receiving an Academy Award for Good Will Hunting, along with Ben Affleck. He also received two Golden Globe awards for both Good Will Hunting and The Martian, and famously played Jason Bourne of the Bourne movie franchise.

Amazing gambling facts: He participated in the World Series of Poker event in 1998, where he was officially the 165th entrant alongside his Rounders co-star Ed Norton.

Rapper Curtis James Jackson III, otherwise known as 50 Cent, is also famous for his entrepreneurial savvy and flashy lifestyle, both of which extend to the blackjack table. While not as technically skilled as some of the others on this list, 50 Cent reportedly enjoys playing blackjack during his Vegas stays and isn't shy about putting serious money on the line, but he also stated that he ‘gambles too much.'

In 2015, he posted a video of himself winning a big hand and walking away with stacks of chips. For 50 Cent, blackjack is more about style, thrill, and showmanship - but that doesn't mean he hasn't walked away with some significant winnings.

Famous for: He has sold more than 30 million albums globally and has received a Grammy award, a Primetime Emmy, 13 Billboard Music Awards, and many other accolades.

Amazing gambling facts: He has openly discussed his gambling problems, stating that he knows he gambles too much. He is known for spending lots of money, particularly on sports betting, and has also been seen with boxer Floyd Mayweather on the gambling floor. He also bet on Mayweather when he fought Manny Pacquiao, putting down $1.6 million.

Socialite and entrepreneur Paris Whitney Hilton may be more commonly associated with fashion and reality TV, but she's also been seen at the blackjack table more than a few times. She reportedly started playing in the early 2000s during her ‘hot,' party-heavy Vegas era and eventually developed a reputation as a frequent VIP room guest.

In some interviews, Hilton has claimed to win up to $30,000 on lucky nights, though like many celebrity gamblers, she views blackjack as entertainment more than a money-making venture. Still, her consistent presence at the tables has earned her a place on this list.

Famous for: Being the great-granddaughter of Conrad Hilton, the founder of Hilton Hotels. She was also a fashion model and reality TV star in the early 2000s with hit shows like The Simple Life and other reality TV series.

Amazing gambling facts: She won $30K while playing blackjack at Wynn Las Vegas and was a brand ambassador for WOW Vegas. The WOW Vegas website has featured Paris Prize Draws, which offers players the chance to win a bevy of prizes by playing online slots.

Shannon Elizabeth Fadal, or simply Shannon Elizabeth, rose to fame in the iconic coming-of-age film, American Pie, but she's also known as a highly skilled poker player. With several notable tournament finishes under her belt, she's among the few celebrities with legitimate gambling credentials. What's less publicized is that she's also a fan of blackjack.

Though poker is her main focus, Elizabeth has played blackjack in charity tournaments and during casino visits. Her understanding of odds, probability, and strategy gives her a leg up, and she's spoken in interviews about how she enjoys the pace and decision-making blackjack offers compared to poker.

Famous for: She was known for being in the movie American Pie as a sexy lead, as well as starring in Scary Movie and other teen films in the late 90s and early 2000s. But more recently, she has garnered attention for being a pro poker player.

Amazing gambling facts: She was named one of the leading celebrity poker players in 2006 and played in the WSOP Main Event in 2005. She won $55K at a special poker tournament in Caesars Palace and made it to the semifinals of the NBC National Heads-Up Poker Championship in 2007.

No list of celebrity gamblers is complete without mentioning Michael Jeffrey Jordan. The NBA legend is famous for his fierce competitiveness - and of course, it extends to gambling. While his betting on golf is more widely publicized, Jordan is also a known blackjack player.

According to numerous reports, Jordan has placed bets of $50,000 or more per hand and played for hours at a time. Like Barkley, Jordan has experienced the highs and lows of gambling. He's not shy about his competitive nature, and insiders say he approaches blackjack with the same intensity that made him an NBA icon.

Famous for: He is a former professional basketball player for the NBA, winning six NBA championships with the Chicago Bulls. He has won multiple awards, including NBA Finals MVP Awards, All-NBA First Team, an NBA Defensive Player of the Year award, and more.

Amazing gambling facts: He has stated that he has had to cover $57K in gambling losses and fork over $1.25 million in betting losses in the golf course as well. He is an avid gambler although admits that he has made ‘reckless decisions' in the past.

Die Hard star Walter Bruce Willis is another celebrity with a longstanding love for blackjack. Over the years, he's been seen playing in casinos from Las Vegas to Atlantic City, often betting in the four-figure range. Willis has even played at celebrity tournaments and high-stakes tables during his Hollywood prime.

Though there are no headlines about him winning millions, casino staff and fans report that he's a skilled and composed player, known for staying calm and focused - much like his on-screen persona.

Famous for: The hit movie franchise Die Hard as well as Pulp Fiction, Unbreakable, Armageddon, 12 Monkeys, Sin City, The Sixth Sense, and, more recently, Glass. He has won a Golden Globe Award, two People's Choice Awards, and two Primetime Emmy Awards.

Amazing gambling facts: Bruce Willis appeared in the hit TV show Friends for free, thanks to a bet he made with Matthew Perry, who played Chandler Bing. He bet that the movie they made together, The Whole Nine Yards, wasn't going to be a box-office success – but the film made over $106 million, and consequently, he lost the bet and appeared in Friends.

You might not expect it, but legendary soul singer Gladys Maria Knight is a major fan of blackjack. In her autobiography, she details a years-long love affair with casino gambling, particularly blackjack. She once admitted to a gambling addiction but eventually overcame it after recognizing its impact on her personal life.

Still, during her playing days, Knight was known to frequent tables in Las Vegas and reportedly won large amounts thanks to her calculated style of play. Her story is a reminder of the double-edged sword gambling can be, but also a testament to the game's allure - even for music royalty.

Famous for: Being an iconic American singer and actress known for Gladys Knight & the Pips; she has won a total of 7 Grammy Awards and is referred to as The Empress of Soul. She was named among the 100 Greatest Singers of All Time by Rolling Stone magazine.

Amazing gambling facts: She once spent an entire night on the gambling tables - and has no idea where the time went. It was a wake-up call for her, and she called Gambler Anonymous right then and there.

Pamela Denise Anderson's blackjack story is as much about drama as it is about winning. In the early 2000s, she famously claimed that she paid off a gambling debt to professional poker player Rick Salomon by marrying him - a claim which Salomon denied. But regardless of the exact details, Anderson's blackjack adventures became tabloid fodder, especially during her time in Las Vegas.

Though she may not be known for strategic brilliance at the table, Anderson's name is often associated with celebrity gambling scandals - making her an unforgettable character in blackjack folklore.

Famous for: Playing the role of Baywatch lifeguard CJ Parker; she also starred in movies such as Barb Wire, Scary Movie 3, Borat, City Hunter, and Baywatch. More recently, she starred in the acclaimed drama The Last Showgirl, for which she earned Golden Globe and SAG nominations for Best Actress.

Amazing gambling facts: She was married to professional poker player Rick Salomon, but more than that, she allegedly lost over $250K in a game of poker. There is also a themed slot with her face and brand, which was first introduced to the public at the Global Gaming Expo.