Betting Celebrities

Hollywood celebrities often have an abundance of money at their disposal, which may tempt them to gamble more than they can afford, leading them down a path towards financial ruin.

Gamblers tend to possess an amusing sense of humor when it comes to gambling – and have even been known to win an impressive sum!

Ben Affleck

Ben Affleck has been making headlines ever since he first entered the limelight as a child, with an immensely successful early career that includes many movies in which he stars and his directorial debut with “Gone Baby Gone”.

Affleck is also well-known as a poker player and has hosted tournaments at different venues. He is well known for his high-rolling habit and proclivity to spend an excessive amount of time gambling.

According to reports, he was banned from the Hard Rock Hotel and Casino in Las Vegas due to an extensive gambling addiction problem.

Affleck has been candid about his past, admitting he struggled with multiple addictions. After eventually conquering them and getting his career back on track, Affleck seems happier than ever and married to Jennifer Lopez with whom he shares three children.

Charlie Sheen

Charlie Sheen, best known for his iconic character on Two and a Half Men as an irrepressibly caddish jingle writer, has appeared in multiple movies such as Platoon (Vietnam War drama) and Wall Street.

He is the youngest son of actors Martin Sheen and Janet Templeton; all his siblings are actors as well.

Sheen was an impressive pitcher and shortstop for his high school baseball team in Santa Monica, California; however, despite this accomplishment he was ultimately expelled due to poor grades and attendance issues.

Sheen later went on to pursue acting, making his debut film appearance in 1974. Since then he has gone on to star in films like Platoon and Wall Street as well as comedy roles. Additionally during this period Sheen dated multiple actresses before marrying Donna Peele in 1995 but ultimately divorcing later that same year. Additionally Sheen led an extravagant lifestyle full of gambling, alcohol abuse and substance misuse.

50 Cent

Curtis Jackson, more commonly known by his stage name 50 Cent, has become one of the premier hip hop artists since releasing his multiplatinum hit “In Da Club.” 50 Cent also enjoys gambling and has an eventful background.

He has amassed a considerable fortune through investing his earnings in real estate, rap music, vodka, fragrances and fashion as well as oil and gas exploration. His holding companies include G-Unit Films and Television Inc., G-Unit Records and Sire Spirits.

His legendary career boasts many popular hits and albums, as well as winning various awards and accolades.

He has made a major impactful on hip hop culture and appeared in multiple movies. But he is also well known for gambling; placing large bets such as his $1.6 Million bet on boxer Floyd Mayweather Jr and other millions-dollar wagers.


Drake is one of the most recognized rappers and singers worldwide. Additionally, he has amassed millions of followers across Twitter and YouTube.

Drake enjoys many pastimes, from traveling and playing video games to gambling in casinos around the globe – where he has both gained and lost hundreds of thousands of dollars at times.

Drake has also been known to wager a considerable sum of money on sporting events such as the Super Bowl and UFC fights, often placing bets through sportsbook.