Behind the Red Velour Curtain: Celebs who Love to Gamble

Celebrities, they’re just like us. Well, not really. In the case of gambling though, the old cliche is actually true. Here are some of the biggest celebrity gamblers famous for playing poker, online casino games, and more.

Drake is not only the most famous Canadian in the world right now. He is also arguably the most famous gambler in the world. The Toronto native has wagered over $1b betting on sports and playing online casino games since 2021.

Drake’s casino of choice is Stake, who he has a partnership with.

Former Playboy bunny and Baywatch star Pamela Anderson became a regular in the Las Vegas poker scene in the mid-2000s when she married poker star Rick Salomon.

According to Anderson, her relationship with Salomon started from private poker games with the World Series of Poker (WSOP) star.

Rounders was more than just a gambling movie with Matt Damon. It was also a look into the real-life of the movie’s star. Damon played in the WSOP in 1998, the same year that Rounders came out. His favourite game is Texas Hold’em.

Damon has gone on to play in multiple other high-profile charity poker tournaments, including the 2009 WSOP.

“This was the biggest rush of my life” – Matt Damon, on playing in the 1998 WSOP

“I want people to understand, gambling is not a bad thing if you do it within the framework of what it’s meant to be, which is fun and entertaining.” – Michael Jordan.

“Victory is a fleeting thing in the gambling business. Today’s winners are tomorrow’s blinking toads, dumb beasts with no hope” – Hunter S. Thompson.

Matt Damon lost $25k at the 1998 WSOP, so it’s fair to say he’s not the best gambler. His Good Will Hunting co-star Ben Affleck, on the other hand, won $356k at the 2004 California State Poker Championship. J-Lo’s husband also reportedly was banned from Las Vegas casinos for card counting.

Tobey Maguire is another mid-2000s star with a big gambling record. The Spider-Man actor reportedly won close to $40m over a three-year period in private Las Vegas and Hollywood poker games.

Drake’s Casino Success: Wins on Live Stream

Most details about celebrity wins and losses are kept under wraps. Not for Drake though. Drake streams his betting for millions of fans to watch. Roulette, where he once won $25m, is his favourite game. The Hotline Bling singer has also had some pretty decent wins playing online slots.

As big as Drake’s wins have been, he is not the best example of responsible gambling. Drake’s casino losses are estimated to be almost $10m.

While most of the big names we’ve discussed here prefer to play poker, plenty also love to gamble online. Just look at Drake and his casino habits, he’s not the only one though.

Pamela Anderson has endorsed multiple poker sites. Ben Affleck, Michael Jordan, and Tiger Woods also reportedly have been known to play at live poker rooms online.

Looking to get in on the action and potentially play with a celebrity? Here are some of the best live dealer casinos in Canada that are worth giving a try.

1. North Casino

With games from world class software provider Evolution Gaming, North Casino has one of the most comprehensive live dealer games libraries in Canada.

2. HellSpin

Don’t let the underworld theme scare you. Hell Spin casino has a great selection of live dealer casino games, including live blackjack, roulette, poker, and more.

3. Joker8

Like the other names on our list of top live casino sites, Joker8 Casino has a strong selection of live casino games. However, Joker8 Casino stands out above the rest with its multiple live casino bonus offers.

4. JackpotCity

JackpotCity Casino has less live casino games than the other casinos here. It makes up for it with its game quality from Evolution Gaming and rewarding loyalty program.

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