Celebrity Blackjack Players: The Stars With Skills.

Ever wondered who out there enjoys your favourite game as much as you do? Ever dreamed of bumping into your idol at a blackjack table, or rubbing shoulders with royalty or the star of your favourite television program? Well, it might not be as unlikely as you thought. The game of blackjack is universally loved, and although you’re unlikely to find blackjack as one of the favourite hobbies of these stars, all of them are known to play the game on a regular basis.

Prince Harry

The ginger prince is renowned for being the bad boy of the royal family. His headline-grabbing antics include dressing up as Hitler for a fancy dress party, playing strip billiards in a hotel room and generally being young and somewhat thoughtless. Harry attracts followers wherever he goes, he is a big fan with the ladies because of his title and his looks, and a bigger fan with the press because of his antics.

Recently Harry was seen in the Wynn Casino in Las Vegas. He was plied with drinks, as is so often the case, and as he slipped into intoxication, with many people observing, he was seen to lose several hundred dollars in a short space of time.

Obviously it wouldn’t look good for the royal family or for his own PR if he was seen to gamble the amounts that he can afford to gamble, but there are suggestions that when he is away from nosey onlookers, in the privacy of the VIP rooms, he takes things up a notch. Still, judging by his card skills on this occasion he should probably leave the gambler to us common folk.

Ben Affleck and Matt Damon

Ben and Matt are familiar faces on the poker scene, and regularly buy their way into the World Series of Poker and other prestigious events. Their love of the game began after they filmed the iconic film Rounders, and once they fell in love with poker they quickly fell in love with blackjack and with gambling in general.

Matt Damon, who played the starring role in that film, was reported to have lost tens of thousands in real casinos whilst he prepared for the role, testing his poker skills against high-rollers to get a better understanding of the game and of what it takes to be poker player. Not only does he have poker down to a tee, but after winning and losing millions on the blackjack tables at the biggest casinos around the world, it’s also safe to say that he probably knows his stuff when it comes to blackjack as well.

Both Matt Damon and Ben Affleck are regulars in Las Vegas and Atlantic City casinos, and depending on where they are filming or vacationing, you could well bump into one of them at a blackjack table. These two are great friends and as well as staring in a lot of films together, they also gamble and hang out together. They once played on same table at a Hard Rock Hotel and casino in Florida and raked in close to a million dollars in a single night of high-stakes blackjack. They were playing over $20.000 a hand and at the end of the night they tipped the dealers and the waiting staff around $150.000.

Michael Jordan

The basketball legend, often hailed as the greatest player ever to step foot on a basketball court, is also a huge gambler and blackjack player. In fact, Michael Jordan will pretty much bet on anything and has been known to win and lose millions of dollars betting on “friendly” games of golf with friends and other gamblers. He has also gambled away similar amounts on craps, poker and more. One of his main loves is sports betting, which is probably not much of a surprise for a man who was embroiled in that world for so long, but it seems that he doesn’t have much of a preference and will happily bet on any sport going.

There is a rumour that the only reason Michael Jordan dropped basketball in favour of baseball for a brief period was because of a suspension imposed after the NBA discovered that he had been betting on basketball games, which is a huge no-no. In fact, even in countries where gambling is legal and encouraged, professional sports stars are not allowed to bet on the sports that they play.

Paris Hilton

The blonde socialite is probably best known for her sex tape or the fact that she is the heir to one of the biggest hotel brands in the world, but believe it or not, Paris also classifies herself as an actress, a singer and a businesswomen. She has made appearances in films such as Zoolander and Win a Date with Tad Hamilton, and she also stared in the 2005 House of Wax remake, which proved to be as popular as you would expect from a film staring Paris Hilton.

Paris Hilton also fancies herself as a gambler and is a regular at the biggest casinos in the City of Sin, but unlike her acting or her singing, this is something that she might actually be good at.

A recent story out of Las Vegas reports that Paris was given $100.000 for work as a disc jokey which she immediately took to the tables. Not long after that she was $50.000 up, and although that is a drop in the ocean in regards to her total wealth, it proves that her card skills are a lot more credible than her singing or acting skills.

Don Johnson

Although not as revered in the acting world as he once was, Don Johnson is well known in the gambling world. Don is probably best remembered for his exploits on Miami Vice, playing the cool and “fashionable” (if you can count anything from the 80s as fashion) cop on the hard and sun-drenched streets of Miami. His performances actually inspired a generation of similar shows and acting styles, and unfortunately it also inspired a fashion trend that the world is still reeling from. Despite these horrors, Don is way cooler as a gambler and card shark than he was as a fictional police officer.

Don is a prolific blackjack player and these days he spends much of his free time playing the game. Reports suggest that Don has earned over $15 million playing the game since he picked it up a number of years ago, going to show that even without a lucrative job on what was one of the most popular television programs of its time, he can still live comfortably.

P Diddy

P Diddy, Puff Daddy or whatever non de plume he’s going by when you read this, is a big-time gambler who loves the blackjack table. He is known for spending big on lavish parties, elegant jewels and flash cars, and his gambling is just as lavish. Reports differ on how much he plays for, but we can safely assume that he’s playing for more than just a few dollars per hand.

Reports suggest that P Diddy once asked for a blackjack table in his dressing room, so that he could play the game before, after and between sets.

50 Cent

The rapper and businessman has also made his way onto the big screen, staring in movies and video games, and lately he has turned towards the gambling industry. 50 Cent is a big blackjack fan, so much so that he commissioned his own game, called “50 Cent’s Blackjack”, which can be played on tablet computers and smartphones. This online game has a community feel and has already proved to be very popular with fans of 50 Cent and fans of blackjack.

In an interview 50 Cent once told an interviewer that he likes to bet $5.000 on single hands of the game, often spending as much as $70.000 in single sittings. 50 Cent said that he only likes to play when there is a lot to be won and lost, which means that even though it carries his name, he’s probably one of the last people who would want to play the 50 Cent Blackjack game.


If a rapper creating a blackjack game seems like a strange move, then you’ll probably be surprised to learn that 50 cent isn’t the only one. Jay-Z, husband of Beyonce and therefore the envy of millions of men worldwide, did the same thing. Jay-Z hasn’t been as outspoken about his love for the game as 50 Cent has, but he is a regular at many of the finer casinos and can be found competing in VIP rooms across Las Vegas.

Jennifer Tilly

Jennifer is currently dating poker professional Phil Laak, also known as the Unabomber, and her love of gambling is well known. In fact these days few remember her as an actress and most recognise her for her performances in televised poker and blackjack tournaments. As well as featuring in the World Series of Poker on a regular basis, along with other televised poker tournaments, she was also selected for the Ultimate Blackjack Tour.

Jennifer has stared in some big films in her time and has acted alongside some of the greats, including Henry Winkler (better known as The Fonz) and Woody Allen. These days when she is not at the poker or blackjack table, she tends to stick to voice work and one of her most famous roles is in the animated adult comedy Family Guy, in which she plays Brenda Swanson. Jennifer has a World Series of Poker bracelet to her name and she is also a regular on the World Poker Tour, where she has 11 “in the money” finishes.

Allen Iverson

Allen is a legendary shooting guard who played in the NBA. The thirty-nine year old played for Philadelphia, Denver, Detroit and Memphis and also won the Most Valuable player award. These days it is gambling that he is most known for and he is a big blackjack fiend. As much as he loves the game though reports suggest that he might not be very good at it, as Iverson is allegedly banned from scores of casinos across the United States because of unpaid gambling debts.

Charles Barkley

Another NBA star who loves to spend an evening at the blackjack tables is Charles Barkley. Not only did Barkley achieve most of what there is to achieve in the sport of basketball, but he made a hefty fortune doing it, and he is more than happy to risk that fortune on a game or two of cards. Charles is huge fan of online casinos, which he plays on mobile devices, betting the big bucks on the move, but he is also known to frequent the land-based casinos whenever he is in town. There are reports that Barkley once won over three-quarters of a million dollars in Las Vegas following a night of intense blackjack action, suggesting that even though his career on the courts is over, he can always make a living on the tables.