100 Best Gambling Movies Of All Time

From owing the mob millions to Elvis impersonators and underground poker parties, movies about gambling include a host of genres and award-winning talent. Below we will explore the best gambling movies of all time (and which made box office history).

Best Gambling Comedies

Bet on the Griswold family winning big in Vegas Vacation (1997:$36.43M) or Nicholas Cage losing $65K and having to marry Betsy (a young Sarah Jessica Parker) in Honeymoon in Vegas (1992:$35.21M). 

In Let It Ride (1989:$4.97M) a man wins EVERY horse bet, while Jason Priestly doubles down in Zigs (2001) to get out of debt. George Segal’s stakes in California Split (1974:$10.9M, Breckin Meyers) includes a celeb lineup in Rat Race (2001:$56.62M) vying for a top prize. Funny Man (1994) has Tim James winning poker in a hauntingly fun way! 

The Hangover (2009:$277.32M) showed debauchery in Sin City post-bachelor party, while dark-humored Very Bad Things (1998:$9.80M, Christian Slater, Jon Favreau) proves you cannot hide the evidence (a dead prostitute). In Saint John of Las Vegas (2009:$0.10M) Steve Buscemi is an ex-gambler drawn back into gambling.

Fear and Loathing in Las Vegas (1998:$10.68M) features Johnny Depp, Benicio Del Toro and Tobey Maguire, while The Grand (2007:$8.11M) stars Woody Harrelson and improv actors playing in a poker tournament.

Asso (1981) has a top poker player, while Christmas Rematch (2004) features players in a unique challenge. Lookin’ to Get Out (1982:$0.95M) includes Jon Voight and Ann-Margret heading to Vegas, and Factotum (2005:$0.81M) stars Matt Dillon, Marisa Tomei and Lili Taylor drinking and gambling.

God of Gamblers (1989) stars Chow Yun-Fat as a master gambler losing his memory, while Freeze Out (2005) includes Tom Sharpe in an ugly high-stakes poker game.

Best Gambling Crime Drama Movies

Apparently, crime pays in Lock, Stock and Two Smoking Barrels (1998:$3.9M), Cool Hand Luke (1967:$16.22M) and Guy Richie’s Revolver (2005:$6.8M, Jason Statham, Andre 3000).  

A good guy bank manager with access to millions is Owning Mahoney (2003:Philip Seymour Hoffman), while Uncut Gems (2019:Adam Sandler) is about a gambling addict. Dinner Rush (2000:$0.11M, Danny Aiello) is about gangsters, while Intacto (2001:$0.30M, Max von Sydow) has people competing to be the luckiest person. 

The Vegas Strip War (1984:Rock Hudson, Sharon Stone) includes a casino owner’s turf war, while All or Nothing (2013:Sharon Clancy) has the ultimate stakes. In Two Dollar Bettor (1951, John Litel), a bank employee hooked on horses recoups his losses, while Regalo di Natale (1986:Carlo Delle Piane) has a poker game with no one to trust.

Guns, Girls and Gambling (2012:Christian Slater) includes Elvis impersonators stealing from an Indian casino. Killing Them Softly (2012:$15.03M: Brad Pitt, Ray Liotta) is about a mob enforcer, while Finder’s Fee (2001) starring Ryan Reynolds is about a winning lottery ticket.

Sharon Stone and hothead Joe Pesci star in Casino (1995:$42.44M), while Paul Newman’s The Hustler (1961:$8.28M) has Fast Eddie Felson taking down Minnesota Fats, with the sequel, The Color of Money (1986:$52.29M) featuring Tom Cruise. For death and poker, watch 5 Card Stud (1968, Dean Martin).

More Gambling Robbery Movies

The Good Thief (2002:$3.52M, Nick Nolte) is about a gambler’s Monte Carlo losing streak, while Phoenix (1998:$0.04M, Ray Liotta) has an addicted cop stealing from bookies. The best bet is Casino Royale (2006) with a $167.45 million payday featuring Judi Dench and Daniel Craig as 007. 

In Dark City (1950, Charlton Heston), a gambler’s in a shady poker game, while Gambling City (1975, Luc Merenda) has a master poker player. Ben Gazzara is in The Killing of a Chinese Bookie with a strip club owner indebted to the mob, while The Music of Chance (1993:$0.31M) features James Spader as a professional gambler.

Best Gambling Romance / Family Drama / Western Movies

Lucky You (1997:$5.76M, Eric Bana, Drew Barrymore) includes a winning poker tournament and losing love, while Kaleidoscope (1966, Warren Beatty, Susannah York) includes lovers gambling in the Riviera and London.

The Cooler (2003:$8.24M, William H. Macy, Maria Bello) is about a gambling jinx who falls in love, while Any Number Can Play (1949, Clark Gable) depicts a casino owner estranged from his family. 

The Big Town (1987:$1.73M, Diane Lane, Matt Dillon) portrays a dice roller in love with a gangster’s wife, while a compulsive gambler’s family receives threats in The Runner (1999, John Goodman). 

Love is in the air for gamblers in Atlantic City (1980, Burt Lancaster, Susan Sarandon) and Havana (1990:$9.24M, Robert Redford, Lena Olin), while Even Money (2006:$0.06M, Kim Basinger, Forest Whitaker) has gambling addictions destroying lives, and Flame of Barbary Coast (1945:John Wayne) has our hero rescuing a dance-hall queen.

Best Gambling Addiction Movies

If you love music, check out the score from Leaving Las Vegas (1995:$49.8M Nick Cage) about an alcoholic ready to check out.

In The Lady Gambles (1949) with Barbara Stanwyck, a husband tries to save his wife from gambling, while Fever Pitch (1985:$0.62M, Ryan O’Neal, Catherine Hicks) covers a journalist hooked on gambling.  

Western Gambling Movies

Explore Sunset Trail (1938) or The Gambler (1980-1991, Kenny Rogers), a four-part TV movies about Brady’s gambling escapades. A Big Hand for the Little Lady stars Henry Fonda (1996). Maverick (1994:$101.63M) includes Mel Gibson, and McCabe & Mrs. Miller (1971:$8.2M) features Warren Beatty.

Best Gambling Poker Strategy Movies

Strategy movies include The Card Counter (2021:Ryan Reynolds), Mississippi Grind (2015), and Croupier (1998:$6.2M, Clive Owen) with a novelist and a big payday. In The Gambler (1997:$0.01M, Michael Gambon) Fyodor must pay debts in 27 days.

In Molly’s Game (1997:Jessica Chastain) Molly Bloom organizes underground games, while Rounders (1998, Ed Norton, Matt Damon) is about loan sharks, law school and poker.

Matt Damon stars in Rounders (1998), while The Gambler is about James Toback’s addiction (1974:$1.31M, James Caan). The 2014 version stars Mark Wahlberg.

Best Gambling Action / Suspense Movies 

The original Oceans 11 (1960:$12.32M) features Frank Sinatra, Dean Martin, Sammy Davis, Jr. and Peter Lawford. Oceans 11, Oceans 12 and Oceans 13 (George Clooney, Brad Pitt) include action-packed casino robberies, while 711 Ocean Drive (1950) is about a greedy bookie.

Best Student / College Gambling Movies

In 21, (2008:$81.16M, Kate Bosworth, Jim Sturgess) MIT students are looking for real money gambling sites to help beat the house, while All In (2006, Michael Madsen, Louis Gosset, Jr., Dominique Swain) depicts a poker tournament. 

Deal (2008:$0.06M, Burt Reynolds, Shannon Elizabeth) covers the World Series of Poker, while Bookies (2003, Nick Stahl, Lukas Haas) has friends facing small-time bookies. Run (1991:$4.41M, Patrick Dempsey) portrays a law student who kills a mob boss’s son. 

All In (2009) is a poker documentary, while High Roller: The Stu Ungar Story (2003) is about Stuey Ungar, a 10-year-old card player who won millions.  

Best Gambling Crime Sting Movies

View Bugsy Siegel’s story in Bugsy (1991:$49.11M Warren Beatty), while Hard Eight (1996: $0.22M, Philip Baker Hall, Samuel L. Jackson) explores surviving the Vegas underworld. Bob the Gambler (1956:$0.02M, Roger Duchesne) depicts robbing a casino.

The Sting (1973, Paul Newman, Robert Redford) is about cons taking down a mobster, while Shade (2003:$0.03M, Joe Nicolo) has hustlers pulling off a sting. Cincinnati Kid (1965:$15.26M) features Steve McQueen, while Tricheurs (1984) is about gambling addiction. 

Smart Money (1931, Edward G. Robinson) entails poker players, while Bad Lieutenant (1992, $2M, Harvey Keitel) is about a gambling addict’s new path. In House of Games (1987:$2.59M, Lindsay Crouse), a psychiatrist helps a gambler, and Luckytown (2000, Kirsten Dunst) has a woman dealing with dad and gambling. 

In La Tueuse (2009, Adrienne Pauly), a pregnant nurse plays poker, while in Big Shot: Confessions of a Campus Bookie (2002, David Krumholtz), a college student is vulnerable to gambling. The Frame-Up (1937, Paul Kelly) covers gangsters. 

Lesser Prophets (1997, Michael Badalucco) explores bookies under surveillance, while in Vig (1998, Peter Falk), a man takes mob money they want back. The Poker Club (2008, Johnny Messner) features a burglar dying on poker night.

Best Sports Gambling Movies

Eight Men Out (1988:$5.68M, John Cusack) is about the 1919 Black Sox scandal. 

For boxing matches, check out Diggstown (1992:$4.84M, James Woods, Louis Gosset Jr.), while Two for the Money (2005:$22.86M, Al Pachino, Matthew McConaughey) covers a former football star. 

FAQ

What is an all-night poker movie? 

If you like Molly’s Game, Follow the Bitch (1996, Michael Cudlitz) depicts single guys at an all-night poker game and the woman who shows up.

What is an unknown but good high-stakes gambling movie? 

Check out Player 5150 (2008, Ethan Embry), about a day trader amidst high-stakes gambling.

Is there a movie about friends who part after a big casino win?

Yes, Sour Grapes (1998, $0.22M, Steven Weber, Craig Bierko) depicts friendship gone bust after a jackpot prize.

Final Thoughts

Whether it is the bustling Las Vegas backdrop in Oceans 11, gambling strategies that eventually go belly-up (Molly’s Game), or bachelor parties that should not mix monkeys, tigers, drugs, and Mike Tyson (The Hangover movies!), gambling movies are SO entertaining – enjoy them all!