
Celebrity and gambling have long gone hand in hand. The golden age of Las Vegas was synonymous with the Rat Pack, and two of its most prominent members – Frank Sinatra and Dean Martin – were both notorious gamblers. It’s hardly a surprise that a lot of celebrities enjoy gambling, after all they have enough money to enjoy the thrill of a win without worrying too much about the losses.
Despite having the cash to afford it, some celebs still take it too far. Many have ended up with a gambling addiction, losing millions over the years. Others have taken part in gambling activities that have broken the law, and an illicit high-stakes celebrity poker game even inspired a successful movie. Let’s dive in and take a look at some of the most interesting and notorious celebrity gamblers.
Ashton Kutcher
His may not be the first name that comes to mind when you think of celebrity gamblers, but Ashton Kutcher is an example of a successful celebrity gambler. Kutcher is best known for roles like the pretty-but-dim Kelso from That 70s Show, or as the fun-loving prankster who presented the MTV practical joke show Punk’d. Because of his on-screen persona, it would be easy to underestimate Kutcher’s intelligence, which worked to his advantage when it came to sports betting.
Kutcher has revealed that he used to place bets for a large American sports betting syndicate, claiming to have won $750,000 in just half a season of college football. Being smart enough to know how to handicap the house, it seems that Kutcher was recruited to place these bets on behalf of professionals who were blacklisted because of their similar talents. A sportsbook manager who worked with Kutcher admitted that they all thought he was just a dumb actor who had gotten lucky a couple of times. They quickly realised their mistake and shut him down, but Kutcher admits that it was a lot of fun.
With those talents, we wouldn’t be surprised if Kutcher has continued betting on sports casually over the years.
Ben Affleck
Although it has been reported that Ben Affleck suffers with a gambling addiction, the evidence suggests that he may simply be a very successful player. Affleck, who has starred in more than seventy movies, and who famously reunited with and married former flame Jennifer Lopez in 2022, claims to never play games of pure chance, such as real money slots. Instead, he sticks very judiciously to either blackjack or poker and evidently, he has done very well in both.
According to the former Batman actor, he once won $800,000 in a single weekend in Vegas at the blackjack tables. He has also professed to know how to do some card counting, which has in turn led to his banishment from the blackjack tables at some real money casinos. If his claims are true, then it means that he must be an excellent blackjack player indeed.
Affleck’s other game is poker, and those who know and have played with him attest to his skill. The legendary screen actor James Woods has even called Affleck his arch-rival in poker. He was also involved in the notorious high-stakes poker game run by Molly Bloom, who also admired his skills as a player.
Tobey Maguire
Speaking of Molly Bloom, we now come to one of the juiciest and most shocking celeb gambling stories of all time. According to Bloom, the innocent-faced Tobey Maguire, star of Spider-Man, The Great Gatsby and The Cider House Rules, may actually be a sly and devious poker shark with a decidedly unpleasant streak. It seems that most people believe that Maguire was the inspiration for the ‘Player X’ character in the movie Molly’s Game.
According to some, it was in fact Maguire rather than Bloom who was the mastermind behind the game that took place in LA’s Viper Room nightclub. An excellent poker player, Maguire was the ringleader of a group that included the aforementioned Affleck as well as close friend Leonardo DiCaprio, luring in players who wanted to sit at the same table as the celebs. By all accounts, Maguire did very well out of the whole deal, although it was Bloom who took the fall when everything unravelled.
Doubtless there were some very shady goings-on that Maguire was directly involved in, including illegally-obtained money in the pot. In the end, Maguire avoided litigation when he settled out of court for $80,000 – a trifling amount of money compared to what changed hands at the illicit games. Although much of what Maguire did during these games is conjecture, it all adds up to a rather unflattering image for the Hollywood star, who took a break from the spotlight for a few years after the allegations were revealed.
Is it Safe for non-VIPs to Play for Real Money?
It goes without saying that unlike Hollywood celebrities, most people do not possess a virtually unlimited bankroll when playing online for real money. Thankfully though, there’s a variety of safe real money casinos featuring slots, card and table games with low wagering limits and designed for casual players who want to gamble without risking losing large sums of money. Playing casino games for real money is no longer just a recreation for the rich, and it can be done at safe and licensed gambling platform with low stakes to accommodate all kind of players.