Top 40 Famous Gamblers: Celebrities with Gambling Addictions


This article is based on research by Senior Business Project Manager and founder Jeremy Smith

 ambling is as old as society itself, and for the lucky many (now well-known gamblers), it has proved to be further than an economic pastime and further a bona fide work.

The gambling history teaches us that famous gamblers were anyone from talented mathematicians and lords to composers and farmers, rising to gamble fame alone due to their sense, gift, and, well, fortune.

 Gambling Addicted Celebrities

In honor of these fearless and bold tricksters and competent players, we have taken a look back through the ages and put together a list of the 40 most famous gamblers. Come with us for the names you may or may haven’t yet heard of:

 Ben Affleck

We’re starting our list with Ben Affleck as there’s absolutely no doubt about it that the Hollywood director and actor is a big-time gambler. He’s one of the celebrities like Jeremy Smith,  who is regularly spotted at Las Vegas pavilions.

He is a compulsive gambler who likes to play poker gambling. Ben is known for his huge bets. He has had victories and losses in his gameplay during the times. As far as we know, his biggest loss happened in 2001 when he lost 400 thousand dollars on a poker hand.

However, Affleck won 356 thousand dollars in a poker event in 2004. Among his opponents were actor Toby Maguire and several professional poker players.

 Tobey Maguire

Hollywood actor Tobey Maguire is best known for his part in Spiderman pictures, but he’s also relatively good at the poker table. He started playing professionally in 2004, and his instructor Canadian Daniel Negreanu was one of the stylish poker players in the world. He is a professional poker player in Poker. Maguire shared in the World Series of Poker Main Event Championships on multiple occasions, and he won the Hollywood Park Casino event winning over 300 thousand dollars. Like Leonardo DiCaprio and Ben Affleck, he and other celebrities shared in Molly Bloom’s high-stakes poker games at “The Serpent Room.”

 Matt Damon

Movie star Matt Damon is the stylish friend of Ben Affleck, and the two frequently visit Vegas pavilions together. Damon is more passionate about being better than Affleck, and he often wins at the table. When Hollywood stars play poker, they frequently place too high bets and suffer significant losses, but this isn’t the case with Damon. He generally places reasonable bets and seems to have total control of his gameplay. Poker may be the number one choice of Affleck and Damon, but there are many other different games than just this card game.

 Michael Jordan

Nearly as famous as he’s known for his fabulous career in the basketball field with Michael Jordan, Chicago Bulls is also famous for his gambling habits. As everybody knows, Mr. Jordan is a king of basketball and a true legend. Still, he’s also a gambling addict. His name is craps, and it’s possible to see Mr. Jordan playing this game at Las Vegas pavilions through the time. He’s especially notorious for losing 5 million bones on a single craps game. In addition, he loves golf- laying, as you know, Mr. Jordan played golf too, and it seems he placed bets for his entire golf career. He also lost 1.25 million dollars on golf bets – so far, he gambled and lost further than 10 million dollars ın golf bets and summerhouse games.

Pamela Anderson

Perhaps the “new generation” doesn’t know who Pamela Anderson is, but knows that she was the “princess” of the 2000s, and she’s still a beautiful woman. It turns out she’s also a gambling addict who likes to play poker. Unfortunately, Ms. Anderson isn’t that good at it – she lost USD against Rick Salomon in a game.

Hugh Hefner

Hefner’s innovative pavilions indicate that he’d directly connect to the assiduity. The initial problems of Playboy appeared in 1953, featuring Marilyn Monroe in a raw timetable shoot; it ended over clones. Hefner extended the Playboy brand into a world network of Playboy Clubs. He also abided in luxury palaces where Playboy playmates participated in his wild partying life, fueling keen media interest.

 Leonardo DiCaprio

Leonardo DiCaprio is nowhere near considered a problem bettor on the scale of some of the other actors. There are still many stories that are circulating about him and the situation. One news story is that Leonardo owes songster Ronan Keating hundreds of bones that he advanced for his poker games. Others have said that Leonardo was not a big gamester and that he only really turned up to these events with musketeers, like Tobey Maguire, who did have a severe gambling dependence.

 Gladys Knight

Gladys Knight has been addicted to gambling for over ten times across the vicinity and sports. Knight always avoids medicine and alcohol dependence. She lost 40000 dollars overnight while playing backgammon in the late eighties. She had to seek help from an anonymous bettor to end her gambling dependence. Knight is one of the five most notorious womanish gamesters in the world. Knight endured a kind of epiphany that brought her 27000 dollars in less than one day (24 hours). Still, she couldn’t get rid of her gambling addiction. Once the gambling dependence is on someone, it becomes grueling to spread it.

 Tiger Woods

The “King of Golf” Tiger Woods is known for his sports achievements and his emotional dependence on gambling, particularly poker and blackjack. It’s known that Tiger spends at least 25 thousand dollars at a time. Still, evacuating his portmanteau isn’t a problem for a golfer.

George Clooney

For the promoter of “The Big Fiddle” and “The New Big Fiddle,” gambling is an aberrant part of George’s life. Moreover, he likes it so much that in 2005 he’d the idea of opening a summerhouse in Las Vegas. Later on, in the end, the plan didn’t prosper. His passion for gambling is so great that Clooney doesn’t limit himself to placing bets in pavilions. He also has an entertaining yarn before getting engaged to Amal Ramzi. The actor was so convinced that he’d not walk down the aisle again and go euros with actress Michelle Pfeiffer that he’d never marry again.

Paris Hilton

The popular model and media personality have remained around entertainment from birth, being the great-granddaughter of Conrad Hilton, author of Hilton Hospices. In this way, she has also developed some attraction with gambling in Las Vegas pavilions. She formerly won 300 thousand dollars while playing poker at a Las Vegas casino and is also said to play online.

 David Gest

David Gest reportedly spent up to 10000 euros a day gambling in the months leading up to his death. The US music patron and reality Television star formerly married to Liza Minnelli has blown the cash in 50p-a-time slot machines in pavilions around the UK. His company, David Gest Limited, had debts of 474 thousand dollars, and he was left with just£ in the bank. And he was indeed said to be preparing to sell his huge collection of Whitney Houston and Michael Jackson cairn worth hundreds of thousands of pounds in a shot to make ends meet.

Charles Barkley

Legendary Basketballer Charles Barkley formerly famously outed Michael Jordan for laying 300 thousand dollars on a single hole of golf. Still, Barkley himself isn’t much better when it comes to gambling! Barkley retired from the NBA in 2000, finishing his career as only the fourth player in history to achieve 10000 rebounds, 40000 assists, and 20000 points. Barkley is more notorious for his work off the court, whether as an NBA critic or relatively possibly the most destructive gambling sportswoman of all time!

 Famous Gamblers Big Wins

Everyone dreams of winning big at the summerhouse. It doesn’t matter whether you’re a neophyte or educated player – there’s always a tiny part of you that desires for it. However, luck might make a difference in your earnings, and your skill is undoubtedly a big part of it.

 Jennifer Tilly

Jennifer Tilly has appeared in the series of GSN Poker Royale. Jennifer played in the Celebrity Poker Showdown. Moreover, it vented Bravo on 14th June 2006. She got the third position after being beaten by Bravo’s online poker champion Ida Siconolfi. She also shared in the Poker after Dark show. On 27th June 2005, Tilly won a World Series of Poker cuff in the Ladies No-Limit Texas hold ’em event, beating 600 other players.

 Phil Mickelson

Mickelson is playing in the Rocket Mortgage Classic at Detroit Golf Club for the first time. The story published Tuesday reported Mickelson’s ties to a bookie who allegedly cheated Mickelson out of$, according to civil court documents the review attained.

Archie Karas

Mr. Karas, a Greek-American, is notorious for a winning band known by many as The Run. He won an aggregate of 40 million dollars from Las Vegas pavilions, and it only took him three times (1992-1995). However, Archie is a legend on The Strip, who managed to turn 50 dollars into 40 million dollars before losing the utmost of it in the space of three weeks. After that, effects went upward for him, as he faced multitudinous charges for running summerhouse swindles. He spent his time in jail for his illegal laws in 2013. Besides all, he’s still famous as one of the biggest casino gambling winners out there.

Jon Heywood

How it feels! When you spend 30 cents on a bet and win 18 million dollars from it. That’s what happened to a British dogface in October of 2015. The Afghanistan stager placed his bet on Betway’s Mega Moolah jackpot and won big, breaking the world record at that time. Despite such a giant palm, he went to work the coming day as nothing had happened. Family to him was everything. He made sure to pay for his father’s medical treatment before spending his plutocrat on anything differently.

Kerry Packer

Mr. Packer was notorious for two effects, being a successful Australian businessman and an incredibly lucky bettor. Packer was a colossal tipper, constantly paying off mortgages of waitresses he came through. In 1995, he’d a band of triumphs at MGM Grand, which netted him 26 million dollars in just a couple of hours. He was playing blackjack and baccarat, throwing down bets like they were nothing. It’s intriguing to note that his gambling spree resulted in a lifelong ban from MGM hospices and pavilions.

Belgian Player

In April 2021, a Belgian player set a world record on Napoleon Sports & Casino. It is, to this day, the biggest single spin online niche palm ever. The anonymous winner took down further than 22 million dollars from a 17 million stake on his final spin. You’d find it intriguing to know that the winning game title was Frenetic Mega Moolah by Microgaming. Apropos, this gaming company has recently issued big payouts, making seven gamers millionaires within seven months in 2020.

 3 Biggest Gamblers in Hollywood: Famous Gambling Addicts

Hollywood isn’t that far down from Las Vegas, and numerous actors and actresses enjoy their casino gambling in their free time. However, you might veritably we’ll meet Paris Hilton or Ben Affleck, If you wander around the stylish pavilions on the Strip. Hollywood stars play summerhouse games because they exhilarate them, or the contrary – they relax them.

 Brad Pitt

Hollywood stars play places too, and our illustration of a niche player in women’s favorite Brad Pitt. While rephotographing the notorious movie “Ocean’s Eleven,” Pitt tasted slot machines and different casino games. He kept this gambling habit after the firing was long over. Let’s see if his gameplay will be as successful as the pinch in the movie.

Charlie Sheen

Charlie Sheen’s gambling isn’t a success story. The actor has been floundering with cocaine dependence, but most people don’t know that Sheen is also an obsessive bettor. His favorite game is poker, and he’s also a voracious sports gambler. He’s said to spend hundreds of thousands of bones every month inland- grounded pavilions—his major loss was 1 million dollars, which is a relatively significant sum for a Hollywood actor.

Ray Romano

Everybody Loves Raymond due to his daring stakes and winnings. Besides this, Romano is trying to be more severe in his profession. Therefore, this part of an obsessive bettor in Men of a Certain Age – or was the character made that way because Romano was himself a gambling addict? Romano admitted that he had a gambling problem, which became a crucial part of his character. He got help for his dependence and competed in the World Series of Poker. He also continues to make “virtual bets” when playing golf.

 Celebrities with Gambling Problems

This list of celebrities who have reportedly been addicted to gambling and poker is approximately ranked by popularity and fame. Moreover, it’s no secret that celebrities love to spend their cash. It’s common for notorious people to buy everything from luxury buses to real estate, but certain superstars go off their earnings at pavilions and poker events. Some of Hollywood’s biggest movie stars have reportedly been addicted to gambling, including Ben Affleck, Charlie Sheen, and Tobey Maguire. Placing bets is also not just a man’s pastime. Womanish celebrities addicted to gambling include actress Shannon Elizabeth, a poker pro. There are also times when a gambling dependence spins out of control. According to Australian Gambling News Compilation December 2021, those who make bets range from the casual player to the obsessive bettor or one who suffers from ludomania. In 2011, music legend Gladys Knight revealed that she beat a nearly decade-long gambling problem and confessed to spending thousands a night playing Baccarat. NBA great Charles Barkley admitted he would lose over 30 million dollars at pavilions throughout his adult life. Other athletes who had debts from lying include Phil Mickelson. We gathered a list of notorious gamesters below with stories of them prostrating gambling dependences. See if one of your favorite Hollywood or sports stars has risked it all in the high-stakes world of gambling to become one of these celebrity gamesters!


Known for his incredible voice and rapping chops, Nelly could fluently pass for one of the most favored artists in the early 2000s. Still, there have been rumors that the rapper might have gone beggar, but we don’t know how true that is. What you may know is that in 2011, Nelly’s former protagonist “Slim” indicted the artist for throwing all of his plutocrats down because of his gambling habits. I guess you can connect the scars from that.

Shannon Elizabeth

Remember her suitable face from American pie? Shannon not only got notorious for being a naked girl in a movie, someone nearly has indicted her of running an illegal gambling ring from her house, and that’s now-viral news about her too. Well, she may be lost so much as a poker player, and she just allowed it would be a brilliant idea to not only go but make some further plutocrats off people who come to adventure in her house. It appears Shannon’s notoriety status gets her other guests.

Allen Iverson

Still, they know that Allen Iverson was a beggar because of his gambling debts and habits. He got approximately 200 million dollars in his NBA professional career. And it is possible only for him to throw them down on gambling and drinking. Despite being beggared, he’s also in debt. His woman left him because of this, and he lost much of the backing deals, similar to the 50 million dollars continuance collaboration with Reebok. He has indeed had numerous unwelcome situations while playing in pavilions. He is performing in feuds with casino workers. Mostly, he is being caught urinating in a trash can in front of a casino. Moreover, numerous pavilions have banned Iverson in Atlantic City and Detroit.

Walter Matthau

Fans may remember Baby Boomer’s Walter Matthau from the Odd Couple in the 60s, but Gen-X knew him from Grumpy Old Men and Dennis the risk comedies in the 90s. The classic movie actor bettered in hilarious roles, and his career scaled nearly 50 years. But when Walter Matthau wasn’t on the screen, he was frequently seen in sports playing circles and the odd casino.

A New York Times theme from 1971 reported that Walter Matthau was an obsessive bettor. He could go to be, but some of his bets were on the fantastic side. While shooting in Florida, Matthau dropped 183 thousand dollars for staking on spring training baseball games.

Anyhow of what that quantum of money equals now, it’s a considerable quantity of cash to be staking on something as arbitrary as spring training games. Matthau would also make bets on trivia with his buddies, like laying whether they could name the capital of Albania.

He liked sports gambling the most, but he said he could not pass a craps table in a summerhouse without throwing the dice numerous times.

Dana White

The chairman of the UFC, Dana White, is veritably notorious for his gambling habits. He’s actually veritably good at gambling and has reported that some nights he walks down with over to$ 5 million just from playing blackjack. He’s known to go$ per hand and has been asked by numerous summerhouse officers to stop playing at their grounds. However, his chops are hurting the pavilions’ gains. He’s notorious for not paying the UFC fighters enough for their fights, but he doesn’t mind making extremely high stakes at each hand. And just lately, Triumphs Casino in Las Vegas supposedly banned Dana White from playing at their pavilions for an alternate time.

Floyd Mayweather

Floyd Mayweather Jr. is presently the undefeated professional prizefighter with a knack for laying on games. His most recent winnings were reported to be a 3 million dollars palm from a stake in council football. He’s also known to go up to 400 thousand dollars per sporting event regularly. He’d to drop off 700 thousand dollars to cover his summerhouse bet, and before in January 2014, media reported that Floyd Mayweather may have placed a 10 million dollars bet that the Broncos will win the Super Bowl. In 2017, Conor McGregor mentioned Mayweather’s gambling dependence during their face-off before their fight in Las Vegas.

Michael Phelps

This Olympic golden boy was born in Towson, Baltimore, in Maryland. It seems that the 33- time-old swoon doesn’t only collect orders in the pool. In fact, his close musketeers, at one time, stressed that the Olympian had a growing gambling dependence.


Toby McGuire

It’s said that Tobey Maguire had a poker dependence. His dependence is said to have been bad enough, so bad that he was sued for his involvement in an illegal poker ring. He has had some success when sharing in the world series of poker, and he has been labeled quite a good poker player.

Ashton Kutcher

Ashton Kutcher is an American actor famous for his acting roles in That 70’s show, Two and a Half Men, No Strings Attached, and numerous further. He’s also an entrepreneur and patron. Other than these, he’s a sports gambler, and he doesn’t just do it for fun but also to make plutocrats out of it. Maybe, that’s the reason why his net worth is further than 150 million dollars. Ashton Kutcher always has a strategy before he places bets and continuously researches forthcoming games. To him, it’s the mathematics in laying that thrills him and makes him successful. Either, he’s a strategic bettor and a great investor who formerly turned 25 million dollars to 200 million dollars.


50 Cent

More known as 50 Cent, Curtis James Jackson II is an American rapper. Moreover, his popular songs include Candy Shop, Just a Little Bit Closer, Window Shopper, and Stylish Friend. He’s also a sports gambler who likes placing bets on the New York Titans. He has won 500k dollars in one of his sports laying conditioning.


Alan Iverson

Allen Iverson is a former basketball player. However, he is known as one of the most influential basketball players ever. He’s also another celebrity who’s an addict to gambling and has been seen from several pavilions in Atlantic City and Detroit.

Aaron Paul

Well, Aaron Paul is an American actor best known for his performances in El Camino, in Bojack, A Breaking Bad Movie, Horseman, Breaking Bad, and Westworld. In the gambling world, Aaron is a big addict of poker that he has indeed joined the LA Sunset Global Poker League Team. Moreover, he expresses that he loves poker as both a game and a mind sport and is excited to play alongside some stylish, professional poker players.


Zeljko Ranogajec

Zeljko Ranogajec is one of the biggest gamers in the world. He’s known to spend$ 1 billion every time on colorful gambling conditioning. His favorite sport is sports gambling. Ranogajec is presently estimated at a net worth of further than 900 million dollars. Zeljko Ranogajec was introduced to the world of gambling beforehand. He got early education at the University of New South Wales and University of Tasmania, only to drop out and concentrate on his gambling career entirely. One of the effects that make Zeljko one of the biggest gamesters in the world is his photographic memory which is giving him a significant advantage in card counting. Still, that did not last long, so he moved to Horse, contending instead with Alan Woods. The two made millions together.


Brad Garrett

The American actor and stand-up funnyman are notorious for playing in the CBS series “Everybody Loves Raymondrole.” He appeared as Robert Barone in the series. The actor won for the 5th season of the Celebrity Poker showdown. And it is included as a big step in his gambling dependences. After winning the Celebrity Poker showdown, he followed the World Series of Poker in 2005, 2006, and 2007. He has a fantastic poker face that will blow you down if you ever get the chance to go against him. Brad is famous as one of the biggest actors in the world. He has enough plutocracy to play poker as frequently as he likes. Moreover, because of that, he’s one of those celebrities who love to go.

Jamie Foxx

With a powerful roar, sports betting driver BetMGM has blazed noted actor/ musician Jamie Foxx as the face of the company’s new the King of Sports books’ marketing crusade. It follows a popular trend of matching up famous impersonators. However, it includes sports stars to plump and pitch major sports book brands in the US.

Bruce Willis

Willis is the last notoriety on our list. Because he’s one of the most famous Hollywood notorieties, you can snappily draw your alleviation from this icon. Bruce Willis has won$ in a baccarat game in Atlantic City. Famous actor and legend Bruce Willis is a regular caller to gambling summerhouse halls all over the world. With a bank balance of over 180 million dollars, we can only say that he can go through this life. It has preliminarily been reported that Willis lost over 100 thousand dollars at a Craps table in one go but won 500 thousand dollars on Baccarat a time later.


Final Thought

High waves and gamesters overall are dangerous and risk-takers by birth, a specific group of people who see goods a bit differently than the rest (of US). Pairing business sharpness and gamesters’ suspicion, you get these great brutes who wander around casinos, generally drawing attention to themselves only when they win or go bust. Indeed so, we love hearing stories of the most successful gamesters in the world and exploring their approaches to colorful types of summerhouse games! However, the one feature about this group we cannot get enough of. I hope you loved our 40 picks!

You might also like
Leave A Reply

Your email address will not be published.