HOLLYWOOD STARS WHO LOVE THE CASINO
Casinos have always had a certain allure. Bright lights, high stakes, the buzz of possibility. They are exciting, glamorous playgrounds where fortunes can be made or lost in a single night. While everyday players flock to enjoy blackjack, poker, or roulette, casinos have long attracted another group too: celebrities. For film, music, and sports stars, the casino floor is both a stage and a retreat. From Frank Sinatra crooning in Las Vegas lounges while betting thousands at the craps table, to Ben Affleck quietly outsmarting blackjack dealers, celebrities have left their mark on casino history. Some are skilled players who’ve won millions, others are thrill-seekers who’ve lost just as much, but all add to the enduring glamour of gambling culture. Here we take a deep dive into the celebrities known for their love of the casino. Their stories, their wins, their losses, and their undeniable influence on the glamorous image of casino life.
HOLLYWOOD STARS WHO LOVE THE CASINO & MUSICIANS AT THE TABLE
Hollywood Stars Who Love the Casino
· Ben Affleck: (The Blackjack Prodigy) Ben Affleck’s relationship with casinos is more than a pastime; it’s the stuff of Vegas legend. At the card table, his focus is electric. In 2014, reports erupted when the Hard Rock Casino politely nudged him away from blackjack; his mastery of card-counting had quietly rattled the house. Unlike most, Affleck loves the game for its brain-teasing strategy and razor-sharp tension.
Affleck has also competed in poker tournaments, including high-profile charity events and the World Series of Poker (WSOP). For him, the casino is not just about excitement but the intellectual challenge and the thrill of outsmarting the odds.
· Matt Damon: (Poker Nights with the Stars) Affleck’s long-time friend and Good Will Hunting co-star Matt Damon shares his passion for casino games. Damon is known for dabbling in poker and blackjack, often accompanying Affleck to Las Vegas trips. He’s participated in charity poker tournaments and celebrity games, though he tends to keep a lower profile than Affleck.
Still, Damon has admitted in interviews that casinos offer a special kind of escape, a world where Hollywood’s biggest stars can blend in with the buzz of the tables.
· Tobey Maguire: (The “Molly’s Game” Poker Ring) When insiders tell tales of Hollywood’s secret poker salons, Tobey Maguire’s name always floats to the top. He wasn’t just a participant, he ruled the high-stakes tables, trading glances and chips with billionaires and superstars in rooms thick with cigar smoke and rumour. Maguire’s ruthless poker face became as famous as his blockbuster roles.
· Ray Romano: (Poker Everyman) Comedian and actor Ray Romano, beloved for Everybody Loves Raymond, is a regular at the WSOP in Las Vegas. Romano openly jokes about his gambling habits, treating poker as both a passion and a challenge. Romano admits to the ups and downs, unlike some stars who hide their losses. His presence at poker tournaments makes him relatable to everyday players who dream of sitting at the same table as a celebrity.
Musicians at the Tables
· Frank Sinatra & The Rat Pack Frank Sinatra didn’t just perform under the Vegas lights; he practically invented its mystique. The Rat Pack’s late-night escapades merged music with midnight risk, turning the Sands Hotel into a living legend. Every clatter of the dice, every glass raised at the craps table, added up to stories that still echo down the Strip.
· Gladys Knight: (The Candid Confession) While many stars glamorise their casino experiences, Gladys Knight took a different path. The legendary singer of “Midnight Train to Georgia” openly spoke about her struggles with gambling. She admitted to being addicted to baccarat and sports betting during the 1980s and 90s.
Knight eventually sought helpand walked away from the tables, but her story is a reminder that even celebrities can face the darker side of casino life.
· Nelly: (Poker and Hip-Hop) Rapper Nelly has made headlines for his poker skills, regularly appearing in celebrity tournaments. He’s admitted to loving the game’s competitiveness, though he often treats it more as entertainment than a professional pursuit.
· P. Diddy: (High-Roller Lifestyle) Music mogul Sean “Diddy” Combs has been spotted at high-limit casino tables in Las Vegas and Atlantic City. His love for the glamorous lifestyle, private jets, champagne, and high-stakes tables makes him a natural fit for the casino scene.
SPORTS LEGENDS AS HIGH ROLLERS & CELEBRITY POKER ENTHUSIASTS
Sports Legends as High Rollers
· Michael Jordan: (Competitive Spirit at the Casino) NBA legend Michael Jordan is as famous for his gambling as he is for his basketball. Jordan’s love of blackjack, poker, and sports betting is well-documented. His competitive spirit doesn’t stop on the court. He has been wagering huge sums at Las Vegas and Atlantic City casinos for years. Though his habits have sometimes sparked controversy, Jordan’s presence at casinos only adds to his mythos as one of the most driven competitors in history.
· Charles Barkley: (Big Wins, Bigger Losses) Charles Barkley’s casino tales are as outsized as his personality. Ten million dollars lost—it’s a staggering figure. Yet Barkley talks about his streaks with the candour and good humour of an old friend spinning stories at the bar. For him, the casino is pure theatre, equal parts chaos and adrenaline.
· Floyd Mayweather: (Boxing’s Biggest Bettor) Boxing champion Floyd “Money” Mayweather has built his brand on wealth and winning. His love of gambling is legendary, especially his massive sports bets and high-roller casino sessions. Mayweather has been known to post photos of himself surrounded by stacks of chips, sometimes betting hundreds of thousands on a single hand of blackjack. For Mayweather, gambling is just another arena to showcase his confidence and appetite for risk.
· Wayne Rooney: (The UK Footballer’s Casino Story) While most of our list is linked to Hollywood and Vegas, one UK star deserves a mention: footballer Wayne Rooney. In 2017, reports claimed he lost over £500,000 in just two hours playing roulette and blackjack at a Manchester casino. For Rooney, it was a cautionary tale rather than a glamorous win. However, it shows that the casino’s pull is universal, from Las Vegas to London and Manchester.
Celebrity Poker Enthusiasts
Jennifer Tilly: (Actress Turned Poker Champion) Academy Award-nominated actress Jennifer Tilly (Bullets Over Broadway, Bound) is one of the world’s most respected celebrity poker players. Unlike many stars who dabble, Tilly is a genuine professional. She won a World Series of Poker (WSOP) bracelet in 2005 and has earned millions in tournament winnings. Her Hollywood glamour and poker prowess make her one of the most iconic figures in both industries.
Shannon Elizabeth: (From American Pie to WSOP) Actress Shannon Elizabeth, best known for her role in American Pie, has also found a second career at the poker tables. She has played in numerous tournaments and is often seen in celebrity charity games.
Jason Alexander: (Comedy at the Cards) Seinfeld star Jason Alexander has a long-standing love for poker. He regularly appears in charity tournaments and has even entered WSOP events. While not as successful as Tilly, his enthusiasm adds a fun, approachable celebrity angle to the poker world.
Aaron Paul: (Breaking Bad, Breaking Pots) Actor Aaron Paul (Breaking Bad) is another Hollywood name who has competed in poker tournaments, including televised celebrity games. His intensity on screen translates well to the poker table.


LEGENDARY OLD-SCHOOL GAMBLERS, WHEN GAMBLING WENT WRONG & THE GLAMOUR OF CELEBRITIES IN CASINOS
Legendary Old-School Gamblers
· Dean Martin & Sammy Davis Jr. As Rat Pack members, Dean Martin and Sammy Davis Jr. helped turn Las Vegas into the glamorous casino hub it is today. Their late-night sessions at the Sands and other venues were legendary, mixing music, showmanship, and high-stakes play.
· George Clooney: (Hollywood Meets Vegas) George Clooney not only starred in Ocean’s Eleven, the ultimate casino heist movie, but also became part-owner of the ambitious (and ultimately unsuccessful) Las Ramblas casino project in Las Vegas. While the casino never came to fruition, Clooney’s love of blackjack and the casino world is well-documented.
· Sean Connery: (Bond and Roulette) Perhaps the most fitting celebrity gambler of all time was Sean Connery, the legendary James Bond. Connery was famously fond of roulette, once winning big by betting on the number 17 three times in a row in Italy. The story has since become part of Bond folklore, cementing Connery’s place in casino legend.
When Gambling Went Wrong
While many celebrity stories are glamorous, not all have happy endings.
· Ben Affleck has spoken about rehab for alcohol and gambling-related issues, showing the fine line between skill and obsession.
· Charles Barkley openly admits to losing millions, though he remains unashamed.
· Gladys Knight revealed her struggles with gambling addiction, serving as a cautionary tale for others.
These stories remind us that gambling, even for celebrities, comes with risks as well as rewards.
The Glamour of Celebrities in Casinos
· Celebrities and casinos go hand-in-hand. From Sinatra’s Vegas heyday to Mayweather’s million-dollar blackjack hands, stars bring a sparkle that elevates the casino floor. Their presence creates stories, legends, and myths that keep the allure of gambling alive.
· Today, while many celebrities still flock to Las Vegas and Monte Carlo, others have embraced online poker and digital casinos. For everyday players, online platforms offer a taste of that same glamour: sleek design, live dealer games, and the thrill of a potential win.
Celebrities have always added glamour to the casino world, but you don’t need to be famous to feel the excitement. Licensed online casinos in the UK offer the same thrill — fair games, safe play, and the chance to feel like a star.
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OVERVIEW
From Ben Affleck’s blackjack brilliance to Frank Sinatra’s craps sessions, from Jennifer Tilly’s poker success to Floyd Mayweather’s flamboyant high-rolling, celebrities have always had a love affair with casinos.
Some play for the thrill, some for the strategy, some for the lifestyle, but all contribute to the glamorous legend of casino culture. Their wins, their losses, and their very presence at the tables shape the way we imagine the casino experience.
And while you may never share a table with Michael Jordan or Jennifer Tilly, the glamour of the casino is available to everyone. Whether in Las Vegas, Monte Carlo, or your favourite UK-licensed online casino.
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