Home Pop Culture Celebrity Gamblers Known for Their Huge Wagers

Celebrity Gamblers Known for Their Huge Wagers

Celebrity Gamblers
A-list Gamblers Known for Making Huge Bets & Winning Big. Pictured, Hollywood heart throb and actor, Ashton Kutcher.
A-list Gamblers
A-list Gamblers Known for Making Huge Bets & Winning Big. Pictured Celebrity and Hollywood actor, Charlie Sheen.

A-list Gamblers Known for Making Huge Bets. Checklist of notable celebrities known for making vast wagers, some huge losses and even bigger wins. 

Gambling is not a pastime that is restricted to a specific group of people. Instead, it is enjoyed by people from every walk of life worldwide: from the day worker who gambles a bit online after a long shift to the A-list celebrity who wagers more money than most people earn in a year. 

Below you’ll find the most significant celebrity gamblers known for their vast wagers. These celebrity household names can often be found enjoying a bit of gambling in their spare time (while the rest of us may only dream about such bets, wins, and losses). 

Charlie Sheen

Charlie Sheen’s personal life has been in the spotlight for a long time. Especially after it came to light that the Two and a Half Men star was battling multiple addictions, including sex, alcohol, and drugs. One that wasn’t covered as extensively was his penchant for gambling. 

The actor has made (and lost) bets up to $1 million while playing poker. While divorcing his ex-wife Denise Richards, the severity of his gambling addiction became public. Rumor is that he was gambling almost $200,000 a week. While he could afford it at the time due to his exorbitant acting salary, it was still an insane amount of money. 

In 2012, he stated that he had retired from gambling. One would assume that would mean that he wouldn’t be involved in anything to do with wagering or betting. However, just years later, in 2016, he was implicated in an illegal sports betting ring. As they say, old habits die hard.

A-list Gamblers
A-list Gamblers Known for Making Huge Bets & Winning Big. Pictured Ben Affleck, Hollywood actor.

Ben Affleck

Most recently known for his role in the DC films Suicide Squad and Justice League, Ben Affleck is one of the most recognized faces in Hollywood. However, the star also has a particular love for gambling that has led him into trouble. 

His biggest wager on record (that he unfortunately lost) occurred in 2001 while playing a game of poker. In a short time, Ben lost a staggering $400,000. Despite this, he was still regularly seen at Vegas casinos. Especially around 2004, when he won $356,000 after participating in a poker tournament. 

Today, he is most likely gambling at online casinos like those found on SlotSource. After being found guilty of counting cards at the Hard Rock Casino in Vegas (now the Virgin Hotels Las Vegas), he was banned from it and many other casinos on the Strip. 

Floyd Mayweather

Floyd Mayweather (or Floyd Mayweather Jr., to be correct) is a famous American boxer known for his ruthlessness in the ring. Because of this, he is one of the most well-known (and well-paid) athletes in the sport. That was, however, until 2017, when he retired. 

Even before his retirement, Floyd openly admitted that he had some problems with gambling—particularly sports betting. This problem has prompted him to make some genuinely wild bets, including $3 million on a football game in 2012.

While this may seem like an absurd amount of money, it worsens. Reports say that in 2017 alone, Floyd’s losses from gambling amounted to almost $50 million. Thankfully, he also occasionally wins, like in 2014 when he won $4.5 million in a single month by betting on the NFL. 

Tobey Maguire

Best known for his role as Marvel’s Spider-Man, Tobey Maguire is one of the most successful celebrities on this list regarding gambling. This could be attributed to the fact that, in 2004, he began playing as a professional poker player. 

Celebrity Gamblers
A-list Gamblers Known for Making Huge Bets & Winning Big. Pictured, Hollywood heart throb and actor, Ashton Kutcher.

Since then, he has participated in the main event of the World Series of Poker numerous times. He also visits Vegas casinos often to partake in high-stake games. Being involved in events like these has led to substantial wins for the actor, including a $300,000 win at the Hollywood Park Poker Tournament. 

Things turned sour, however, when the actor was busted running an illegal poker ring. Estimates state that the actor made between $40 and $50 million while the poker ring was active. He was ultimately sued by some of the players he had dupped but settled the lawsuit to avoid more trouble. 

Ashton Kutcher

Rising to fame on That 70s Show, Ashton quickly made a name for himself in entertainment. Eventually, he even took over the prime role in Two and a Half Men, replacing fellow gambler Charlie Sheen. 

While his bets aren’t as ridiculous as other celebrities on this list, Ashton has admitted to playing stupid while making bets on sporting events. Using his admittedly dumb persona, the actor bet using a mathematical formula that gave him the best odds of winning. 

He is said to have won around $750,000 in a single month during his betting spree. However, the sports betting firm he was using quickly caught on to what he was doing and put an abrupt end to it. 

50 Cent

It should be no surprise to see at least one famous rapper on this list. After all, what goes better with the hip-hop lifestyle than betting? However, this rapper is known for making some ridiculous wagers—even on things where he will see no return on his investment. 

One of his most infamous bets was for $1 million on a Super Bowl match in 2012. Thankfully for the star, his bet was correct, and he cashed in big. However, his reasoning for placing the bet had some people scratching their heads, as he stated he did so due to the voices in his head. 

Then again, in 2017, the celeb made headlines when he bet Floyd Mayweather $750,000 that he wouldn’t be able to read a single page from the first Harry Potter book. However, he made this bet in good humor, and the figure ultimately went to a charity of Mayweather’s choice.