Top 6 Celebrity Gamblers

June 7, 2018 4:41 pm by Ken E

It’s no secret that Hollywood celebrities love to splash their cash on gambling nearly as much as they do on fancy parties, fine Hollywood homes, private planes and maybe even drugs, sex and alcohol for some. In this article, we examine the Top 6 Celebrity gamblers and their casino games of choice that they love dearly.

Matt Damon

Matt Damon and Ben Affleck


Popular for his lead role as Jason Bourne among many other starring turns, the Hollywood star also loves to gamble and can be spotted frequently in Casinos along with his fellow Oscar winner (writers of the Best original screenplay for ‘Good Will Hunting’) and childhood buddy from his native Boston, Ben Affleck.

It is alleged that Matt Damon was also involved in Molly Bloom’s illegal gambling ring along with Affleck and Tobey Maguire which took place in 5-star hotels in both Los Angeles and New York. Texas Hold’em Poker is Damon’s game of choice and he can be regularly spotted along with his friend Ben Affleck at select luxury hotels in Las Vegas where they are frequently invited as high rollers.

50 Cent

50 Cent


If being shot nine times and surviving wasn’t lucky enough, 50 Cent, aka Curtis James Jackson III, also has a happy knack for getting good odds converted into big gambling wins. Recently, 50 Cent has become somewhat of a poster boy for those who have cashed in on the cryptocurrency boom.

Four years ago, 50 Cent released his fifth studio album, ‘Animal Ambition’, and made it available to buy online using bitcoin. While sales of the album itself was estimated to net him around CAD $640,000 in bitcoin sales at the time of release, those bitcoins are now worth approximately over CAD $9 million.

50 Cent is known to be an avid sports better and it is rumored that he won approximately CAD $640,000 betting on the Giants to take out the NFC Championship game in 2012, between the Giants and the San Francisco 49ers. Of course, the Giants and 50 Cent won.

Charlie Sheen

Charlie Sheen


To say that Charlie Sheen is well-known for his proclivities to indulge in excesses is a wild understatement.

Well-known for his popular lead role as wild man, Charlie Harper, in the long-running hit comedy TV series “Two and a Half Men”, Charlie Sheen has allegedly been gambling non-stop in one form or another since his youth.

Known for his impeccable comic timing and sense of humor, Sheen is also a sports fanatic who likes to bet on the outcome of sports events, usually the bigger, the better. Sheen earned around CAD $2.3 million dollars per episode of “Two and a Half Men”, certainly having enough cash to spend lavishly on casinos and monster all-night drug binges.

Sheen’s ex-wife Denise Richards who filed for a divorce in 2006, stated that Charlie was spending around CAD $26 000 per week on sports betting.

Floyd Mayweather Jnr

Floyd Mayweather Jnr


When it comes to pure earnings from gambling (or pure earnings from any source), few celebrities (or even professional gamblers for that matter) can match the kind of cash that Floyd Mayweather Jnr has managed to accumulate.

The man is by all accounts, boxing’s first ever billionaire. Not counting his already astronomical earnings from his successful boxing career (including August 2017’s much hyped bout against UFC star, Conor McGregor), Mayweather has made well over CAD $13 million thanks to his sports betting alone. For example, in 2012, Mayweather he took home over CAD $1 million from a bet on an US college football game between Oregon & Arizona State.

Mayweather chose not to bet on the big fight between himself and Conor McGregor. He really didn’t need to as he’s reported to have made in excess of over CAD $330 million from that fight alone.

Michael Jordan

Michael Jordan


His “Air-ness”, Michael Jordan is considered to be one of the biggest celebrity gamblers in history. Back in 1993, when Michael Jordan first retired, rumors came to the surface that the best player in NBA history retired due to his extreme gambling habits. One unsubstantiated rumor went as far as to allege that then NBA Commissioner David Stern banned Jordan from the game until he cleaned up his act.

An article surfaced in a sports magazine during the 1993 NBA playoffs, in which it was stated that Jordan was accused of gambling during the series between his beloved Chicago Bulls and the New York Knicks. The Bulls were down 2-0 at the time of publication. After the article was published, the Bulls went on a 4-0 game-winning run to close out the best of seven series and advanced to the NBA Finals, which they promptly won.

Ray Romano

Ray Romano


Never let it be said that we don’t save the best for last. Ray Romano became popular and a household name with the sitcom “Everybody loves Raymond”, a TV show in which Raymond showcased all the bittersweet trials and tribulations, challenges and benefits of a middle class suburban family living in the United States in the late 90s and early 2000s. The show bought Romano stellar fame and a wealth that was previously unknown in television at the time..

Romano became one of the most popular faces on television and was one of the first writer-actors to receive astronomical pay cheques from a TV show. ‘Everybody loves Raymond’ was as popular as ‘Friends’, and Romano was counting the cash. However, as the show was drawing to its inevitable closing season, Ray Romano battled with a huge gambling addiction that almost cost him everything.

In 2009, Romano produced and started in a new TV show, called “Men of a Certain Age”, in which he played Joe Tranelli, a middle-aged man with a gambling problem. At the time, few people knew that the character of Joe was actually autobiographical. Some years after the show ended in 2011, Ray admitted that he was actually Joe.

Having recovered from his addiction, Romano today gambles on virtual bets, but doesn’t visit casinos or visit online casinos as much as he once did and now only plays for fun. He still loves to compete and plays in the World Series of Poker for fun only, realistically admitting he does so knowing he doesn’t stand a chance of winning. He just loves to play.

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