Many celebs feel the constant need to keep the life party alive. Hence, they tend to take side-interests when not onscreen or on social media. Gambling is a common hobby that most famous people adopt. You may be shocked to see some celebrity names in this review.
For those interested in experiencing casino gaming like the stars, RetroBet offers a VIP experience with a substantial welcome package of up to 150,000 kr plus 500 free spins, split across four deposits. The platform features games from leading providers like Pragmatic Play, NetEnt, and Play’n Go, offering both RNG and live dealer options for an authentic casino atmosphere.
#1 Ben Affleck: Mastering the Game of Blackjack
When Ben is not in his Batman suit, he is in Las Vegas playing Blackjack. Affleck is not just your random gambler. He was reportedly stopped from entering a Las Vegas casino for being “too good.”
The administrators at Hard Rock Casino accused him of counting cards and banned him from their Blackjack tables for life.
Ben Affleck does not only play at land-based casinos across the world but also online. He once mentioned in an interview that he won about $800k from playing Blackjack online. Perhaps he’s just that good!
#2 Matt Damon: A Poker Enthusiast Both On and Off-Screen
Damon has been good friends with Ben Affleck for decades. He once mentioned to Ellen Degeneres that they have both been playing Blackjack for 30 years. With all these years of experience in the bag, it’s no wonder Ben is so good at the game. However, Matt Damon is equally amazing at blackjack as his friend.
Damon played a poker player in the 1998 film Rounders just because he loves gambling. In this film, Matt counts cards to win big at tables in casino halls. He was once sighted at the Hard Rock Casino in Las Vegas playing blackjack. To him, gambling is simply a fun activity.
If you’re looking to develop your own gaming skills, you can start with igt free slots to practice and learn various game mechanics before moving on to real money play.
#3 Tobey Maguire: High-Stakes Poker Player
Your friendly neighborhood Spider-Man is a Poker hustler in real life. Tobey’s Poker adventures have inspired multiple movies, a blockbuster movie, and a couple of 6-figure lawsuits.

Maguire organized several private Poker games alongside other famous individuals in the early 2000s. These secret gambling sessions had big names like Matt Damon and Leonardo DiCaprio in attendance.
Tobey Maguire and some other participants in one of his Poker games were once sued for participating in a Ponzi scheme worth more than $44 million. Maguire settled by paying $80,000 to the plaintiff.
#4 Michael Jordan: Betting Big at the Blackjack Table
Jordan loved himself some golf bets quite alright. However, he did not just stop there. He also knew about casino games, especially the Blackjack tables.
Michael Jordan was involved in one of the greatest reversals of fortune ever in a casino hall. On the fateful day, he placed $40k bets per hand. At one point, Michael was almost down by $500k. However, he remained resilient and decided on $15k bets instead (not advisable – gamble responsibly).
Suddenly, Jordan started winning. Overnight, he managed to win as much as $800k, which, in addition to the $500k buy-in amount, made him up to $1.3 million.
#5 Paris Hilton: Spinning the Reels of Slot Machines
This American Sweetheart has partnered with leading gambling brands, the latest of which is WOW Vegas, a leading social casino enterprise. Paris, in her own time, likes to explore nervy slot games.
However, most recently, she had some questions regarding illegal gambling to answer in front of the Louisiana Senate alongside Ryan Seacrest.
#6 Charles Barkley: Betting Big on Everything
The former NBA basketballer gambled throughout his active playing career and well into retirement. Charles eventually got addicted to gambling, losing up to $20 million at some point. He mentioned in an interview that he has probably won a million about five or six times; however, he has lost a similar amount up to 20 times, dating back to the 1980s.

Things got so bad at some point when Barkley owed the Wynn Casino in Las Vegas $400,000 and faced the threats of a potential lawsuit. Furthermore, Charles spoke about how he quit gambling for two years to recover and improve.
#7 Tiger Woods: Poker and Strategic Gambling
If Golf had not worked out, Woods could have become a professional Poker player. His habits have never been hidden from the public.
Tiger has organized or participated in many poker tournaments, including expensive buy-ins and charity events. These secret or public competitions often have other celebrities in attendance, too. Furthermore, fans have seen him playing alongside other professionals at multiple Las Vegas casinos.
Conclusion
Celebrities may have hobbies like normal people, but theirs could be very expensive. These individuals often participate in high-roller tournaments, unlike most normal people, who are casual bettors at casino halls or gambling sites.