Home EntertainmentCelebrity Hollywood’s Biggest Bettors: A Look at Celebrity Gamblers

Hollywood’s Biggest Bettors: A Look at Celebrity Gamblers

by Scott Kacsmar
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Tobey Maguire Poker

Celebrities aren’t that much different than the rest of us. They just have way more resources to fund their gambling habits. It sounds cliché, but you can often find a star in Las Vegas at the casinos looking to have a fun night of gambling.

Let’s take a look at some of the more famous celebrity gamblers, past and present, out there trying to feel the thrill of winning like the rest of us.

Drake

What a great time to be an ultra-famous and super-rich rapper when sports betting is legalized in so many places. If Drake wants to bet $100,000 on a 3-leg parlay, he more than has the capital to pull that off. This is a man who reportedly spent close to $400,000 for his mattress.

Drake has allegedly played $200,000 spins of roulette at casinos, so dropping huge money on sports bets is no big deal to him. He seems to support a variety of sports teams, mainly whoever is hot at the moment, and his lack of allegiance makes him an ideal candidate for spur of the moment big bets. He’s not betting with his head or heart as much as just vibes.

It also reportedly isn’t working out that well as Drake lost over $2 million on UFC bets alone in 2022.But he did redeem himself a bit when he bet $700,000 on the Chiefs (-110) to win the Super Bowl 57 over the Eagles, which they did.

But when you have money like Drake, you can afford losses better than the common man.

50 Cent

While many sports bettors had to wait for PASPA to be overturned in 2018 to legalize sports betting in their state, 50 Cent has been betting on sports for many years now. He has publicly shown some of his best wins like in 2012 when the Giants beat the 49ers to advance to the Super Bowl. 50 Cent made $500,000 on that upset, a game that required overtime and a muffed punt by the 49ers.

50 Cent is also no stranger to betting on boxing, and even has some ideas for prop bets for boxers out of the ring. He once infamously bet $750,000 to boxer Floyd Mayweather, another known celebrity gambler, to see if he could read a single page of a Harry Potter book to prove that he is literate. If he got through the page without messing up, 50 would donate $750,000 to charity. That would have been fun to see play out, and with 50 Cent’s income, he is good for paying his debts.

Norm MacDonald

The late, great comedian Norm MacDonald would have been a blast to go to Vegas with back in the day. He was a big fan of everything from sports betting to casino games.

The stories of Norm’s gambling days are both comical and depressing:

  • He suffered a bad beat on a bet in the 1998 NBA Finals in the game where the Utah Jazz only scored 54 points against the Bulls.
  • He once threw $60,000 into the ocean in Atlantic City in an effort to stop gambling altogether. It didn’t work.
  • He once bet $25,000 on Manny Pacquiao to win a boxing match with a payout of only $3,000 and without knowing anything about boxing.
  • His biggest sports bet was $400,000 on the 1998 Falcons to win Super Bowl 33 over Denver, and that was not even close to hitting, as Denver won by 2 touchdowns.

Adam Sandler told the story shortly after Norm’s passing from cancer in 2022 of how he found $25,000 in casino chips from Atlantic City in Norm’s fridge. Norm had won big on Friday and instead of cashing out, he wanted to figure out how he could avoid paying taxes on the win. By Monday, Sandler saw Norm and asked if he cashed the chips yet, and Norm told him “I lost it all!”

If only Norm could have had a little more luck in life. He will be missed.

“Yeah man, they call gambling a disease, but it’s the only disease where you can win a bunch of money.”

– Norm MacDonald

Jennifer Tilly

The Liar, Liar actress known for her unique voice – she voices Joe’s wife Bonnie on Family Guy – and busty outfits is also a winning poker player. In 2005, she won a WSOP bracelet and has continued to appear in tournaments.

Tilly has amassed over $1 million in winnings from poker in her career. According to an old interview, she was ranked 30th on the all-time earnings list for women poker players.

Ashton Kutcher

While known for playing silly characters in That ‘70s Show and Dude, Where’s My Car?, actor Ashton Kutcher is actually a successful sports bettor. He was ahead of the curve with studying the data and using algorithms to arrive at his picks. He once had a 4-week hot streak that was so good that a sportsbook banned him from future bets.

Kutcher has long been serious about sports betting. In 2015, he invested in Unikrn, a bookmaker for eSports (video games) betting. He is also a big believer in AI and will likely make use of AI going forward in his sports betting process.

The Molly’s Game Crew (Tobey Maguire, Leonardo DiCaprio, Ben Affleck, Matt Damon)

You may be familiar with the 2017 film Molly’s Game starring Jessica Chastain as Molly Bloom. It was based on the 2014 memoirs of the real-life Bloom, who was involved in hosting illegal high-stakes poker games on Tuesday nights at the Viper Room or Beverly Hills Four Seasons Hotel for some of Hollywood’s top actors and other celebrities such as directors Todd Phillips (Joker) and Nick Cassavetes (The Notebook).

Eventually, members of the Italian and Russian mafia got involved with the games, and Bloom was arrested by the FBI for illegal gambling with mobsters and had to go on trial. The games ended in the late 2000s.

It is a very solid movie, and there is a character named Player X, played by Michael Cera, who is reportedly a composite character based on the real-life actors who participated in the poker games such as Tobey Maguire, Leonard DiCaprio, and Ben Affleck.

Maguire, everyone’s first friendly neighborhood Spider-Man, was arguably the ringleader of this game as he is obsessed with poker and takes it very seriously. Maguire is best friends with DiCaprio, and the two have long been seen together at clubs over the years. DiCaprio, the eternal bachelor, supposedly didn’t want to pay the $5,000 buy-in to the game despite being worth millions, and he wasn’t as serious of a player as Maguire.

Ben Affleck also showed up for the games, which reportedly made winning $20,000 feel like you lost because of how much money was being spent at these events. Where there’s Affleck, Matt Damon can’t be far behind, and the Rounders star did show up as Affleck’s guest one night and reportedly lost $50,000. Affleck wrote the check for that, a good friend indeed.

When you are as young and successful as those guys were, it is not crazy to think high-stakes poker games would be something they’d take an interest in.

Maguire and DiCaprio later starred together in the remake of The Great Gatsby in 2013, and that depiction of luxury probably paled in comparison to some of the wild poker games they got up to.

What else would you want to do on a Tuesday night with millions in the bank, old sport?

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Scott Kacsmar
NFL football picks are Scott Kacsmar's expertise, serving as his main focus. He has contributed to various sports websites and blogs, such as NBC Sports, ESPN Insider, FiveThirtyEight, and, JoeWager. Originating from Pittsburgh, Scott maintains a love-hate connection with the Pirates.

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