The appeal of casino games is not lost on Hollywood, in fact, many well-known stars enjoy a good game of blackjack or slots just as much as the next person. The grand palatial casino resorts of Las Vegas have attracted celebs since the days of Sinatra and Dean Martin, and they continue to do so today.
It is not just the glitz and glamour of the Vegas Strip where gamblers in Hollywood place their high-stakes bets and test their luck. They have also jumped into the world of online casino and sports betting, accessing the same platforms that players from all over the US play at. On this page, we will look at some of their greatest wins and triumphs.
Poker and blackjack are two of Hollywood’s most popular games of chance, but to diversify the list, we have also included major slots wins and jackpot prizes Below is a smattering of the biggest wins by some of the most famous people on the planet.
Drake’s $38-40 Million in Roulette
The rapper has a passion for sports betting, and is known for making high-stakes bets on major sports events. He also plays casino games like roulette, and in 2024 Drake won around $40 million in a single night.
Ben Affleck: $800,000 in Blackjack
Affleck is a respected blackjack player who has been embroiled in scandals and big wins alike. He won $800,000 playing blackjack at a Las Vegas Casino before being asked to leave, on suspicion of card counting. Later, Affleck confirmed he had been counting cards.
Dana White: $7 Million in Blackjack
The UFC founder is just as famous for his gambling antics, with both staggering wins and losses. He has made plenty of bold claims about his abilities and wins, but the biggest win he had was in Vegas in 2022.
Tobey Maguire: $2 Million in Poker
Maguire was one of the biggest poker players in Hollywood, but he became part of an underground high-stakes poker scene in the 2000s that ruined his reputation in Hollywood.
Pamela Anderson: $1 Million in Slots
When she was on a promo tour in Las Vegas, Pamela Anderson hit a $1 million jackpot on slots. It was one of the biggest ever by a celebrity, and helped her get valuable partnerships with casino brands later.
Charlie Sheen: $250,000 in Table Games
At the height of his fame, Sheen was rumored to gamble up to $200,000 a week, and reportedly scored a $250,000 win during a Las Vegas trip in the mid 2000s.
Not All Glitz and Glory
It is not all plain sailing for celebrity gamblers; just as there are stories of great fortune, there are plenty of stars who have made bad bets and ended up losing immeasurable sums of money. The most notable of which are Michael Jordan, Nicolas Cage, Allen Iverson, and Drake. In some cases, these were one-off losses that made the tabloids and then quietly disappeared. But for others, they became financially crippling moments of realization of the dangers of gambling.
For it doesn’t matter how much a player has, they should always be mindful of the risks and never spend more than they can afford to lose. Tiger Woods may have played blackjack for $25,000 per round, but at the time, his career earnings were just shy of $2 billion. The most important aspect of gambling is for players to play within their means, create budgets, and avoid getting emotionally charged by losses. Learning to quit while you’re ahead is really the best skill you can develop when gambling, and taking regular breaks helps keep you fresh and focused.
