1) Rounders (1998)
Anyone else think they want to play professional poker after Rounders? Even if you’re not among this group, if you like poker you’ve probably seen this movie (and if you haven’t, stop reading this and go watch it now).
This movie follows poker prodigy Mike McDermott (played by Matt Damon) and his girlfriend Jo who wants him to quit gambling — until his longtime friend Worm is released from prison, and needs to pay off a debt owed to Russian mobster Teddy ‘KGB’ (played by John Malkovich — we recommend watching to hear his Russian accent alone), and decides to get back in the game. If you want the pressure of being in a high-stakes poker game without actually being there, this is perfect for you.
2) Casino (1995)
A personal favorite, Casino has everything you I could want in a gambling movie — Joe Pesci, Sharon Stone, made men, and a moving picture that shows a decade of change in Las Vegas.
This movie follows Sam ‘Ace’ Rothstein, an associate of the Mafia, but also a sports handicapper sent to run the union-led Tangiers Casino. The story follows his career at the Vegas casino and trials & tribulations in his personal life.
If you like incredible actors and performances, you’ll appreciate this movie, but if you’re a Las Vegas enthusiast or have romantic notions of Vegas, you’ll really love & appreciate the decade-long progression of Vegas shown in the movie.
3) The Gambler (1974)
The title of this movie pretty much says it all. The Gambler follows Axel Freed, an English professor with a gambling problem gambler that’s snowballing. Unable to stop after pleading from his girlfriend and mother, Freed continues to make poor decision after poor decision, until the mob wants his life — he decides to make a big move, that hopefully results in a big win to pay off his debts.
There’s a 2014 remake starring Mark Wahlberg, but we recommend the original version (with the original ending) for a more realistic, less suave portrayal of gambling addiction.
4) Casino Royale (2006)
A list of poker movies probably wouldn’t be complete without at least one of James Bond’s films.
Casino Royale (2006) follows James Bond on his first mission as 00, in a poker game where Le Chiffre must play to win back a sum of money and remain a banker to terrorists, and Bond must prevent Le Chiffre from winning and stop his evil banking. Watch Casino Royale and see everything you love from Bond movies like action, poker, with one exception — his signature drink is replaced with a Vesper instead of his usual martini.
5) High Roller: The Stu Ungar Story (2003)
Sopranos fans will delight at getting to see Michael Imperioli (Christopher Moltasanti) in this theatrical retelling of well, the Stu Ungar story. If you’re a card game fan and you have no idea who Stu Ungar was, you’ve got to see this movie.
The movie starts with Ungar on his deathbed, relegating stories to a stranger about his life growing up as the son of a bookie, and his subsequent career shift to professional card player.
Stu Ungar was gambling at the age of 10, and won millions playing poker, blackjack, and other card games — the movie covers personal controversies too, showing his divorce, cocaine addiction and other issues.
Spoiler alert: the movie contains a reimagining of one of the most outrageous bluffs in poker history — and it’s all true.
