The Good, the Bad, and the Lucky: Memorable Celebrity Gambling Stories


Making money from gambling is by no means easy. It is especially difficult if you do not have a lot of money to play with, to begin with. The more you have the greater your chances are of making money yourself.

As celebrities tend to earn massive salaries it should not come as a surprise to you to learn that they tend to make huge amounts of money when they are gambling. Some have even made small fortunes for themselves. Learning about the exploits of celebrities can be motivational.

When you feel more motivated to gamble, you are more likely to win. Positivity attracts positivity. A lot of people approach gambling with a negative mindset and as a consequence do not win when they perhaps should. A negative mindset in gambling can destroy your chances of earning yourself a handsome profit.

This post will explore celebrity gamblers in great depth, telling you everything that you need to know about who the most skilled ones are, as well as exploring and delving into their lives so that you can increase your chance of winning when you try your hand at gambling.

Finding a Reliable Casino to Use

Before delving into the stories of famous celebrities and their gambling habits, it’s first necessary to cover casinos. You need to make sure that you find real money casinos in the USA with good reputations. A casino’s reputation is something you always need to take into consideration if it is not very good then of course you won’t get the best treatment or care. A good way to find out if a casino’s reputation is positive is to read its reviews.  A casino’s reviews can tell you a lot about them.

Ben Affleck

Ben Affleck is one of Hollywood’s most popular stars. The actor built his reputation starring alongside some of the film industry’s biggest names. Something that a lot of people do not know about the star however is that he is highly intelligent and is also a very good gambler. In fact, in the early days of his career, he actually learned to count cards and ended up making a fortune for himself at the Hard Rock in Vegas. Unfortunately for Affleck though he was caught and security collared him, taking his winnings and leaving him with nothing. That being said before being caught Affleck did indeed make a fortune for himself and in a single night earned $145,000. Affleck was famous for tipping cocktail waitresses and dealers heavily, giving them massive sums of money for themselves, making him, understandably, very popular.

John Cusack

Another very popular Hollywood star who earned a lot of money for himself as a gambler is John Cusack. While there are no especially interesting stories about Cusack as there are with Affleck, the actor is notorious for being a fantastic gambler and has in fact earned lots of money over the years from rolling dice. If you are interested in learning more about his exploits as a gambler you could always reach out to him on social media. Cusack’s career has gone quiet in recent years so perhaps rather than appearing in Hollywood films the actor is making money for himself as a gambler! Bear in mind though that just because some Hollywood stars make money for themselves as gamblers that’s not to say that you can too, at least without research and effort. Becoming a professional gambler is not easy and can take people years to do. If you want to become one then you need to shop around, do your research and learn as much about gambling as you can.


Deadmau5 is one of the most famous DJs that there is. If you are interested in gambling exploits then Deadmau5’s are some of the most entertaining. The DJ has a particular affinity for the risk that is inherent in gambling. For some reason, he loves it. Deadmau5’s interest in gambling started when he was introduced to Matt Bon-Jovi, the brother of Jon Bon Jovi. There have been stories of the musician being down hundreds of thousands of dollars, then only minutes later, earning it back plus more.

Drew Carey

Drew Carey is not the kind of person one would assume was into gambling. However, she most certainly is. Carey’s charm and talent have made her one of the most popular actresses in the film industry. She is known to frequent casinos and play with hundreds of thousands of dollars when she does. One amusing anecdote involving Carey relates to her playing alongside The Simpsons co-creator Matt Simon, with the pair of them being down $200,000 between them. It does need to be reiterated that just because actresses and famous people are content throwing away vast sums of money, you should not be.

Charlie Sheen

Charlie Sheen has, for a long time, been Hollywood’s bad boy. Even now as an older man the actor is notorious for crazy gimmicks and stunts. You should not if you k know anything about the actor be surprised to learn that he has had his share of gambling-related incidents and accidents. During the actor’s divorce with Denise Richards tabloid newspapers revealed that he had been blowing over $200,000 per week on gambling. The actor has since claimed that he has given up on gambling.

Gambling Responsibly

Throughout this post, reference has been made to the dangers of gambling. If you are somebody with an addictive personality then you need to do everything that you can to limit the amount that you play and spend. You will be pleased to know that most online casinos give players the opportunity to set their own limits. Setting your own limits will help you to save yourself money and restrict the amount that you can lose. Do not exceed the limits you set for yourself. Make sure that you do not sign up for another casino and just play there when you are gambling, either.

If you are a fan of gambling then you need to make sure that you stay in control at all times. Do not get into the habit of spending more than you can afford to lose. Spending more than you can afford to lose can be bad for your performance as a gambler.

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