I am not a gambler. (Unless you count the 5 times in my life I’ve stepped foot inside a casino and put $10 into a slot machine on my grandma’s behalf.) All that being said, I still love Las Vegas … and I also love movies that center around high rollers. Meaning the kind of people who think nothing of shelling out hundreds, thousands, or even hundreds of thousands of dollars during a night at the casino.
Here are 5 of my favorite movies about high rollers:
Molly’s Game – What’s most incredible about this Oscar-nominated movie is that it’s based on a true story. (Another true story: Molly Bloom (Jessica Chastain) is a friend of a friend of mine.) Molly was a champion skier until a severe injury dashed her hopes of competing in the 2002 Olympics. She then moved to LA and became involved in the world of underground high-stakes poker — with several A-list celebrities. But eventually Molly got in over her head as the Russian mob became involved in her games. You know you want to find out what happened to her in the end…
Rounders – This is the only one on my list that isn’t actually set in Vegas, but that doesn’t mean it’s any less intense. It stars (a very young) Matt Damon as a skilled but naïve poker player who teams up with his old childhood friend “Worm” (Ed Norton) to compete in underground poker games in an attempt to pay off a debt Worm owes. But — surprise, surprise — they get in too deep, and just like in Molly’s Game, some bad Russian dudes show up to spoil the fun. Once you watch this one you’ll see why it’s become a cult classic!
Casino – Often considered the BEST movie about the high-roller lifestyle, this crime drama from director Martin Scorsese earned Sharon Stone an Oscar nomination for her role as Ginger McKenna, the wife of Robert De Niro’s Sam Rothstein. Sam runs a Vegas casino for the Mafia and is known for his violent temper … and this is probably the point where I should mention that if you tend to not like movies with intense violence, this probably isn’t the pick for you.
Ocean’s Eleven – A much more lighthearted option would be this 2001 heist flick that’s a remake of the 1960 Rat Pack film. It stars George Clooney, Julia Roberts, Brad Pitt, Matt Damon and more and revolves around a complicated plan to rob three of Vegas’s biggest casinos … at the same time. It’s edge-of-your-seat fun that spawned two successful sequels — and we’ll also be getting an all-female spinoff (Ocean’s 8) this summer!
Swingers – OK so maybe this comedy isn’t exactly about high rollers, but it DID spawn the phrase “so money” and does star Jon Favreau BEFORE he became a high roller himself. (He’s the guy who directed Iron Man, The Jungle Book and more.) Jon plays a recently dumped twentysomething who reluctantly drives to Vegas with his best friend (Vince Vaughn) in attempt to get out of his funk. Watch it and see why it’s one of my all-time favorite movies.
What are your favorite movies about high rollers?