5 Hollywood Actors Deep into Gambling

Postimage 5HollywoodActorsDeepintoGambling actorinset 900x480 - 5 Hollywood Actors Deep into Gambling

It’s not a surprise that big Hollywood actors are drawn to an excessive and extravagant lifestyle. Casinos offer precisely that. And they have been the ruin of several talented artists. Take a look at five Hollywood actors who were or still are deep into gambling.

Charlie Sheen

Charlie Sheen has demonstrated questionable behavior countless times. So, it is honestly not surprising that gambling is one of his addictions. Apparently, he has been gambling immoderately ever since his youth.

The actor’s ex-wife, Denise Richards, claims that Sheen spent more than 200,000 a week just to feed his desire to gamble. According to Richards, big losses were not uncommon. His favored types of gambling include poker and sports betting. However, Charlie Sheen says that his gambling days are part of the past.

Ben Affleck

One of the all-time most famous Hollywood actors, Affleck is deep into card games, especially poker and blackjack. He is known to have lost a poker hand of 400,000 dollars.

Back in 2001, Ben Affleck recognized his gambling addiction and went into rehab to treat it, as well as other problems. Nonetheless, over the following years, he has fallen back into the casino life, nurturing a spiral of gambling and drinking.

He has had both lucky and disastrous episodes. In 2014, Affleck won the California State Poker Championship. In the same year, he was banned from playing blackjack at a Las Vegas casino for winning repeatedly.

Tobey Maguire

The most widely beloved Spider-Man, Tobey Maguire is also a famous poker addict. Maguire became so blinded by his addiction that he even participated in an illegal gambling ring moving millions of dollars, for which he was sued in 2011.

He is a successful player on the World Series of Poker, although the only factor that can be credited for his success up until now is his unhealthy addiction. He is rumored to have won 10 million dollars at poker tournaments.

Postimage 5HollywoodActorsDeepintoGambling setinmovie - 5 Hollywood Actors Deep into Gambling

Matt Damon

Matt Damon has accompanied his childhood friend, Ben Affleck, in many of his gambling endeavors throughout the years. He has been spotted frequently at luxury casinos and hotel resorts in Las Vegas. His favorite game is said to be Texas Hold ‘em poker.

Along with Tobey Maguire, Damon was one of the stars caught in the scandal of the illegal gambling ring in 2011.

Ray Romano

Extremely successful for his role in Everybody Loves Raymond, Ray Romano has had to enter Gamblers Anonymous to tame his addiction. His journey into rehab has been proven successful since the actor has dropped his unconscious habits.

Now, Romano gambles moderately. He still plays on the World Series of Poker, although he has been quite unsuccessful. Additionally, he likes to bet on golf. The actor claims that he doesn’t actually use real money for most of his current gambling activities.

To different degrees and severity of consequences, all of these actors have found trouble in their gambling habits.

6 Rumor Sites to Read Celebrity Gambling Stories

Postimage 6RumorSitestoReadCelebrityGamblingStories manusinglaptop 900x480 - 6 Rumor Sites to Read Celebrity Gambling Stories

Have you ever wondered where you can find the best celebrity gambling rumors before most people? Look no further. Here, we have six of the top sources.

Oh No, They Didn’t!

The name of the site is pretty self-explanatory. On Oh No They Didn’t! you will find the biggest celebrity rumors and scandals before they hit any other place around the web.

The site is a community of gossip writers who are constantly submitting new content to the platform. As there are so many contributors, the articles are varied, unique and extremely fast to arrive.

Celebs from all art and entertainment spheres are featured. If there were to be another celebrity gambling ring story breaking out, rest assured that Oh No They Didn’t! would have it all covered immediately.

Perez Hilton

Perez Hilton is self-proclaimed gossip media royalty. If there is any conceivable rumor about a celebrity, it is much likely featured on Perez Hilton. So, be sure to check it to see which gambling rumors were posted exclusively on the blog.

The site’s unwavering devotion to rumors makes it sometimes come up with obviously fabricated stories. Many times, though, Perez Hilton is the first to give factual updates about stuff you never saw coming.

That’s because he is such an established insider in the entertainment industry. He has scooped one-on-one juicy details from huge stars.

Postimage 6RumorSitestoReadCelebrityGamblingStories onset - 6 Rumor Sites to Read Celebrity Gambling Stories


Who hasn’t heard about TMZ? The reporters for the site are probably the number one enemy to celebrities across the entertainment industry. TMZ covers a massive amount of rumors. You will never be bored browsing the website.

TMZ has helped celebrity gambling stories see the light of day in the past and provided the most detailed information about the episodes.

Pop Sugar

On Pop Sugar, you will find countless photo galleries with candid pics and paparazzi shots. When a celeb is caught in the middle of some gambling trouble, be sure that Pop Sugar will notify the event with loads of images.

This is a light, fun and witty website filled with the rumors you don’t want to miss.


Celebuzz has built a reputation of being quite snarky and aggressive in its celebrity reports. In the event of breaking gambling rumors, Celebuzz would definitely be very judgmental. And the writers would try to dish out as many dirt as possible.

Postimage 6RumorSitestoReadCelebrityGamblingStories laptopman - 6 Rumor Sites to Read Celebrity Gambling Stories


The focus of Dlisted is in providing the best celebrity gossip stories as hilariously as they get, making fun of the unfortunate situations in which stars are caught. The commentary is always sharp and comedic.

Can you imagine how Dlisted would go about the repeated gambling downfalls of actors like Charlie Sheen and Ben Affleck? Or that infamous multi-million gambling ring back in 2011?

In addition to these six websites, there are also several gambling-specific blogs, news platforms and online magazines that regularly publish celebrity gambling stories.

3 Actresses Who Are Really into Gambling

Postimage 3ActressesWhoAreReallyintoGambling actressincamera 900x480 - 3 Actresses Who Are Really into Gambling

It’s not only men that can get addicted to gambling. In fact, many female celebrities have experienced that reality. However, some of them have been very successful and are now pro gamblers. Check our three actresses who are really into gambling.

Shannon Elizabeth

Shannon Elizabeth is an actress, producer and model, whose second occupation as an expert poker player has been quite successful. Elizabeth has been proving that women are more than capable of defeating men at the poker tables.

Shannon Elizabeth found overnight success with the movie American Pie. She went on to play in the mega-flick Love Actually, co-producing various movies along the way.

When it comes to her poker side career, which is basically becoming her main career, Elizabeth is said to have won almost 250,000 dollars.

Postimage 3ActressesWhoAreReallyintoGambling modelactress - 3 Actresses Who Are Really into Gambling

Pamela Anderson

Actress, model, producer, activist and showgirl, Pamela Anderson has also added gambler to her resume. She was reportedly very unlucky one night when she lost 250,000 dollars in Las Vegas.

Anderson was brutally honest during an interview in which she admitted to having paid a gentleman with sexual favors so he would clear her debt. Curiously and quite hilariously, they ended up falling in love. To this day, she still likes to gamble.

Jennifer Tilly

Jennifer Tilly is an Academy Award-nominated actress who is also known as one of the most successful gamblers in the world. Poker is her go-to and she has won various World Series titles.

Tilly’s addiction has led to episodes of extreme stress, though. For instance, in 2012, the actress and expert gambler were seen sleeping on benches during the World Series. She has admitted that the game causes her severe anxiety, which is why she quit the tables for a while, only to end up returning.

Throughout their careers in acting and gambling, these women have gone through downfalls and triumphs.

3 Iconic Musicians with a Gambling Addiction

Postimage 3IconicMusicianswithaGamblingAddiction handandchips 900x480 - 3 Iconic Musicians with a Gambling Addiction

Even the most gifted and respected music artists can go a few steps too far when it comes to gambling. Some of them almost entirely destroyed their own lives.

The truth is that massive amounts of money and countless ways to easily earn more can be a very dangerous combination. These three musicians are perfect examples of that.

Lemmy Kilmister

Lemmy Kilmister was an English musician, best known as the founder of the legendary band Motorhead. Kilmister had deeply rooted gambling habits. Slot machines were his number one choice at casinos.

Postimage 3IconicMusicianswithaGamblingAddiction lemmy - 3 Iconic Musicians with a Gambling Addiction

In the documentary about his life and work, Dave Vanian, a fellow artist, talks about Lemmy’s gambling problems. Apparently, he visited a gambling club in London regularly, where he spent huge amounts of money and even hung out with various outlaws and gangsters.

Gladys Knight

Gladys Knight is known as the Empress of Soul. Besides her outstanding musicianship, her gambling addiction is also widely discussed. However, Knight has been one of the celebrities who has tackled the issue more honestly.

In her autobiography, Gladys Knight admits that she was so deep into sports betting and baccarat that she almost lost everything she has worked for.

One day, she woke up extremely inebriated after an intense night of gambling. She forgot to take her son to school. It was the turning point for Knight. She knew her fall was imminent if she didn’t change her lifestyle.

Frank Sinatra

A lovely voice and stage presence can go hand in hand with a heated temper at casinos. Frank Sinatra was proof of that. He was even rumored to mistreat the casino staff when they would deny him credit to gamble.

Postimage 3IconicMusicianswithaGamblingAddiction franksinatra - 3 Iconic Musicians with a Gambling Addiction

A famous episode took place in 1967. Sinatra and Carl Cohen, the manager of the Sands casino, engaged in an argument that ended up with Cohen having chips thrown at his face and Sinatra missing two teeth.

At some point in their journeys, these three legendary artists have let gambling control their lives.

5 Celebrities Who Are Known to Be Gambling Addicts

PostImage 5CelebritiesWhoAreKnowntoBeGamblingAddicts playingpoker 900x480 - 5 Celebrities Who Are Known to Be Gambling Addicts

In all spheres of entertainment, you can find examples of people who have fallen for the trap of gambling addiction and have been betting with varying degrees of success. Here we have two athletes and three musicians.

Tiger Woods

Tiger Woods is almost as known for his recurring gambling problems as he is for his outstanding talent for golf. Woods allegedly bets up to 25,000 dollars for each hand in blackjack. His addiction has led the MGM Grand Casino in Las Vegas to limit his gambling to a maximum of 1 million dollars.

Postimage 5CelebritiesWhoAreKnowntoBeGamblingAddicts Tigerwoods - 5 Celebrities Who Are Known to Be Gambling Addicts

During many of his gambling sessions, he was accompanied by two of his friends and fellow athlete gambling addicts, Michael Jordan and Charles Barkley.

Allen Iverson

Allan Iverson is a prime example of how irresponsible gambling can destroy everything a person has worked for. He was a skilled basketball player who made 200 million dollars with the NBA.

Then, in an endless loop of gambling and drinking, Iverson threw it all in the trash. To this day, Allen Iverson is reportedly in debt. The addiction also cost him his family and business life, as his wife left him and many sponsors abandoned their deals.

The severe issue reached such a point that Iverson engaged in altercations with casino employees and has been banned from several gambling venues in Detroit and Atlantic City.

50 Cent

The rapper is famous for being an avid sports bettor and for placing some of the most extravagant bets you can think of. He bet 2 million dollars on Floyd Mayweather (another big-time gambler) at a boxing match against Manny Pacquiao.

Postimae 5CelebritiesWhoAreKnowntoBeGamblingAddicts rapper - 5 Celebrities Who Are Known to Be Gambling Addicts

On another occasion, he bet 500,000 dollars on the New York Giants. The team ended up defeating the San Francisco 49ers and winning the Super Bowl.

CeeLo Green

CeeLo Green is the stage name of the acclaimed musician Thomas DeCarlo Callaway. In fact, Cee-Lo is the name of a popular casino game with varying rules and played with three six-sided dice.

CeeLo Green must really love gambling, then. You have probably noticed that much of the imagery in CeeLo’s videos and on the artwork for his music revolves around gambling, casinos and Vegas.

Sully Erna

Sully Erna is the lead vocalist for the successful metal band Godsmack and also performs solo since 2010. One of his most beloved games is poker.

Postimage 5CelebritiesWhoAreKnowntoBeGamblingAddicts sully - 5 Celebrities Who Are Known to Be Gambling Addicts

The tattoo on his back kind of says it all. Erna has inked four aces in flames along with the phrase “no justice”. Curiously, the tattoo was done after he lost a poker game.

Some of these celebs have ruined their lives while others have continuously had luck by their side. That’s gambling 101.

2 Famous Athletes with Gambling Problems

postimage 2FamousAthleteswithGamblingProblems tablecasino 900x480 - 2 Famous Athletes with Gambling Problems

A career in sports can make an athlete incredibly rich almost overnight. And celebrity sportsmen are not immune to fall into the traps of an immoderate gambling lifestyle. The more money you have, the more money you want. But the luck will eventually dry out if you choose to gamble, even online following proper US gambling laws.

When that time arrives and all the gambling problems come to the surface, the monetary and interpersonal losses can grow massive. Take a look at two successful athletes who have tasted the bittersweet thrill of gambling.

Pete Rose

Every time a list is published with the names of the biggest celebrity gamblers, Peter Rose is part of it. That’s because he has probably paid the highest price of them all. Peter Rose is an iconic baseball player. But many people have gone on to know him as a big-time baseball bettor.

postimage 2FamousAthleteswithGamblingProblems baseballplayer - 2 Famous Athletes with Gambling Problems

Around the time he was managing the Reds, Rose used to bet at least 10,000 dollars every day. The punishment for his conduct is unparalleled. He was banned from Major League Baseball.

And although he has made outstanding contributions to the sport throughout his career as a player and a manager, Rose is ineligible to enter the Hall of Fame.

Peter Rose is a living example of how a gambling addiction can lead to unmeasurable losses not only in money but to one’s life work and reputation.

Michael Jordan

Considered by many as the greatest basketball player to have ever lived, Michael Jordan has had his share of gambling problems. Being such a famous athlete, it is only natural that many of the stories surrounding his gambling addiction were merely fabricated.

postimage 2FamousAthleteswithGamblingProblems jordanshoes - 2 Famous Athletes with Gambling Problems

However, it is known that Jordan has bet thousands or millions of dollars at golf courses and casinos.

Many people say that, to this day, he still gambles frequently. Others even state that Jordan only stepped away from basketball for a couple of years and tried out a baseball career so that the NBA wouldn’t condemn his gambling addiction.

Other athletes with severe gambling problems include Charles Barkley, Floyd Mayweather and John Daly.