Celebrity Casino Stories: Inside the Celebrity Casino World

Celebrity gambling has been around for as long as casinos. Even A-listers enjoy testing their luck at gambling. If you want to find out which celebrities gamble, their favorite games, their wins, and their losses, keep reading – this piece will reveal the most famous casino stories.

Celebrity Gamblers and Their Games

A casino has many different games on offer to gamblers. From slots to poker and live dealer to blackjack, and all their variants, the options may seem unlimited. But what games do celebrities like to play?

Michael Phelps

Former American swimmer Michael Phelps comes first in our list of celebrity gamblers. The most successful athlete in Olympic history with 28 medals, Michael Phelps is famous for dropping huge sums of money on the poker table at different casinos. Upon his World Series of Poker debut, the swimmer bought into the $5,000 no-limit hold’em event.

Phelps started his casino gambling with online casinos before visiting brick-and-mortar establishments. Unfortunately, the poker lover developed unhealthy playing habits and his friends and family had to seek a solution for his obsession with gambling. He made a lot of money but also lost heavily in both online and offline gambling.

Brad Pitt – Poker and Blackjack

Brad Pitt is next on the list of our celebrity gamblers. The actor loves poker and blackjack, among other casino games. He initially developed an interest when preparing for his role in the hit movie Ocean’s Eleven. Pitt practiced his gambling skills at different casinos to get better at the gambling scenes needed for the shoot. He remains fond of playing these casino games.

Ray Romano – Poker

Ray Romano has multiple talents beyond being an actor. The star of Everybody loves Raymond is not only accomplished in comedic circles but has also become a reputable gambler.

Ray Romano loves playing poker as his game of choice. He has even participated in the World Series of Poker a number of times.

Ben Affleck – Poker and Blackjack

This Academy Award winner loves playing poker and blackjack. In 2013, the actor featured in the crime thriller Runner Runner where his character goes up against a fictitious empire of online casino websites.

However, Affleck developed an interest in gambling before acting in this movie. A member of casino staff once reported that Affleck is one of Hollywood’s most generous stars when it comes to tipping.

Big Celebrity Wins and Losses

Celebrities tend to be wealthy, so when they visit a casino, you can expect to find them in the high-stakes rooms putting down huge sums of money. Huge bets can bring about huge wins, but they can also translate to massive losses.

Jennifer Tilly

Jennifer Tilly is an Academy Award nominee who has starred in many films, though she is likely most recognized as the voice of Tiffany Valentine in the Chucky franchise. The actress and poker player has made a fortune through casino gambling.

In 2005, Tilly participated in the World Series of Poker. She competed against 600 other players and won about $160,000, becoming the first celebrity to win a World Series tournament.

Ben Affleck

Ben Affleck’s name pops up once again in this category. One of his most significant wins came in 2004, when he accrued $350,000 in a poker championship. A report also suggested that the American actor and filmmaker once bet $60,000 on blackjack and won $800,000.

However, Affleck has also suffered significant casino losses. The blackjack and poker enthusiast experienced his biggest loss in 2001 after betting on a losing hand in poker. The event saw Affleck lose $400,000.

Charlie Sheen

Born Carlos Irwin Estévez, Charlie Sheen is a famous actor with millions of fans. He is perhaps best known for playing a fictionalized version of himself in the series Two and a Half Men. Sheen is another actor with a fondness for gambling, but this has led to a bit of an addiction.

Reports suggest that Sheen spends nothing less than $200,000 at the casino weekly. He’s usually seated at the high-stakes poker table, but the actor also loves sports betting. His most significant loss was approximately $1m on sports betting.

Tiger Woods

When you think of golf, Tiger Woods is the name that will likely pop into your head. Woods is one of the most famous golfers of all time. However, he is fond of playing with aces, diamonds and spades as well as clubs.

Woods is an avid blackjack player, and the star once wagered $25,000 and lost. However, it wouldn’t be surprising if Woods has lost more than that in a single sitting, as he is believed to have a $1m betting limit in one of the top casinos in Vegas.

Pamela Anderson

This Canadian-American model and actress has a special affection for gambling. However, luck wasn’t on her side on the night she lost $250,000 playing poker. Despite this, Anderson can still be found spending some of her free time in the many Las Vegas casinos.

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Unusual Celebrity Casino Stories

From shocking gambling moments to casino business deals, here are some unusual celebrity casino stories.

Tobey Maguire

Perhaps best known for playing Peter Parker in the original Spider-Man movies, Tobey Maguire was part of the duo that inspired the events of the film Molly’s Game. The actor infamously set up poker tournaments for A-list clientele, including Leonardo DiCaprio and Matt Damon. Indeed, the ‘Web Spinner’ and poker enthusiast has won more than $10m gambling. Reportedly, the actor regularly won over $50,000 per night.

Ben Affleck

Clearly, no celebrity gambling list would be complete without Ben Affleck. The American actor has been gambling for nearly two decades and once donated his winnings – over $400,000 – to charity. In 2014, Affleck was banned from playing blackjack at the Hard Rock Casino in Las Vegas. This ban came after he was caught counting cards, which most casinos frown upon. However, the actor never reacted to or confirmed these accusations.

Jennifer Lopez

The actress and singer known as J.Lo is well-matched to husband Affleck, as she also has a love for gambling. She is a green table and roulette enthusiast.

Maybe J.Lo takes after her mother, Guadalupe Rodríguez, who is a real gambling star. Lopez’s mother once won about $2.5m on the slot machines in the Borgata Casino in Atlantic City .

Rafael Nadal

Spanish tennis star Rafael Nadal discovered his talent for poker when playing with friends at home in Mallorca. He now spends a lot of his leisure time at casinos. Nadal even said that he might consider joining the poker circuit once he ends his tennis career, and he has an interest in participating in the World Series.

George Clooney

Last on this list is George Clooney. The actor has been a regular customer at casinos for a long time. The Hollywood hunk, along with his Ocean’s Eleven co-star Matt Damon, used to visit different casinos following their time on the set of the film. Clooney even attempted to acquire a casino in Nevada in 2005. However, he is yet to become a casino owner and has had to settle for visiting casinos as a player.

Celebrity Casino Tips

Celebrities usually hit the casino with a few gambling tips up their sleeve. These tips have helped them land some of the biggest wins at the casino, and they can be used in both land-based and online settings:

  • Play at the best casino: Whether you are visiting a brick-and-mortar or online casino, ensure that you are choosing the best. This means finding out about the table limits, house edge, and more. When playing online, make sure that it’s a legit casino with a license.
  • Avoid chasing losses: Losses are inevitable in gambling. It may even happen at the start of events. Avoid losing your head and betting big to recover your losses.
  • Utilize the best bonuses: From sign-up bonuses to loyalty programs, casinos offer various types of bonuses. Check regularly for promotions, and don’t miss out on them.
  • Learn the techniques: Casino games such as poker pit you against other players. Learn the art of bankrolling and the key moves before you play. You can check out some free tools online to learn.
  • Avoid alcohol: Avoid alcohol when betting for real money. Alcohol lowers your inhibitions, influencing you to make reckless decisions.
  • If you are winning, quit!: Learn how to quit if you are on a winning streak. It can be tempting to keep playing, but with gambling, you can lose at any time. So, learn when to call it a day.


Many famous faces love gambling in their leisure time. They often spend big bucks, so they can either lose or win big. This goes to show that the chance of winning big can captivate anyone. Ultimately, regardless of how big your bankroll is, it’s important that gambling remains a healthy form of entertainment and not an addiction.

Author: Tanya Fields

Campaign Acquisition Manager Length with RC: 1 year, 9 months Favorite Casino Game: Starburst Background in iGaming: Opened the iGaming Department at Hard Rock Atlantic City in 2018 in both Customer Service, and then CRM, prior to moving over to RC in January 2021 Location: Based in NJ at the RC HQ Content: Occasionally, but only as it pertains to RC