A Running List of Celebrities That Gamble

As we mourn the death of legendary actor James Caan, we look back on some of his best work. He is perhaps most well known for the early role that made his career – playing Sonny Corleone in Francis Ford Coppola’s The Godfather (1972), for which he was nominated for an Academy Award for best supporting actor.

Another well received performance was his role in the 1974 classic The Gambler, the story of a professor who spirals deeper and deeper into the world of gambling. This film, directed by Karel Reisz, explores what draws people to gambling, and allowed Caan to display his full range as an actor. According to Caan’s character Axel Freed, the appeal of gambling isn’t the money, but rather the thrill of beating the odds.

Despite playing a gambler in one of the most famous gambling movies in cinema history, Caan himself was not known to have been much of a gambler. However gambling is a very popular pastime among the rich and famous.

Let’s take a look at some celebrities who fancy a visit to the casino.


Ben Affleck

Ben Affleck is one of Hollywood’s A-listers who is almost as well known for his romantic relationships as he is for his acting roles and his work behind the camera.

He has won two Academy Awards: one for best screenplay for Good Will Hunting (1998) and one for best picture for Argo (2013), which he directed. His highest-profile relationships have been with Jennifer Lopez (his co-star in the widely panned 2003 film Gigli), Jennifer Garner, and Gwyneth Paltrow.

Affleck had a brief career as a professional poker player. He was also heavily involved in the high-stakes celebrity poker games hosted by Molly Bloom. He frequently played with Leonardo DiCaprio, Tobey Maguire, Matt Damon, and Nelly.

His skills and gambling interests go beyond poker too. Affleck is reportedly so good at blackjack that he has been asked by several Las Vegas casinos to not play there. He is such a talented blackjack player that casino staff assumed he was counting cards.



Drake is one of the biggest musicians in the world, having sold over 170 million albums to date. The Canadian’s most recent album, ‘Honestly, Nevermind’ just dropped on June 16th of this year.

Drake has attracted a lot of attention for his gambling livestreams where he places high-stakes bets at online casinos. He is rumored to have bet millions on a single blackjack hand or roulette spin.

Online casinos have made it much harder for us to know which celebrities like to gamble, since we aren’t able to see them going into a physical casino or sitting at the gaming tables. Playing at online casinos like Scores gives all players as much privacy and security as they want. This can be very attractive for celebrities who prefer to maintain some privacy in their personal lives.

But thanks to the rise of livestreaming by both celebrities and regular folk, we are still able to get a glimpse into the world of celebrity gambling. In fact, gambling streams could be considered just another genre of gaming streams.


Charles Barkley

At the height of his career, Charles Barkley was one of the most talented basketball players on the court. Between 1984 and 2000 he played for the Philadelphia 76ers, the Phoenix Suns, and the Houston Rockets. He averaged 22.1 points and 11.7 rebounds per game. He was also a member of the ‘Dream Team’, the US Olympic basketball team that dominated the competition in 1992 and 1996.

After retiring, Barkley became a popular basketball pundit, and has been commentating for TNT since 2000. He has also spent a lot of his time gambling. His game of choice is blackjack, but he also enjoys betting on sports, and has been known to place a bet on his own performances in celebrity golf tournaments!


Gladys Knight

Gladys Knight is rightly known as the “Empress of Soul”. She has made a massively important contribution to music over the course of her nearly 50-year career. She has won seven Grammys and numerous other awards, including an NAACP Image Award and a BET Lifetime Achievement Award. She also has a star on the Hollywood Walk of Fame.

During the 1970s and 1980s she became deeply involved in gambling, playing blackjack and baccarat for hours on end. She decided to quit gambling when she realized it had begun to take over her life and was interfering with her ability to be a good mother.


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The collective team of Parlé Magazine. Twitter: @parlemag

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