The 21 Best Gambling Movies of All Time (11-21)
I recently posted my picks for the best poker movie scenes of all time:
Let’s now have a look at the best movies about gambling.
Over the years, many films have been made about the much wider sphere of gambling. Accordingly, I’ve broadened my list of movie recommendations to a most appropriate number — 21.
Admittedly, there’s some gray area as to what constitutes a “gambling movie.” My criteria is as follows. In order to qualify, gambling must play a significant role in the film. It must be portrayed in a somewhat realistic manner. Some movies contain excellent gambling sequences — for instance, Rain Man and Going in Style. But these two film classics aren’t really about gambling, so neither made the cut.
Moreover, other notable movies have a gambling undercurrent throughout. Requiem For a Heavyweight, Seabiscuit, and Secretariat immediately come to mind. However, there’s very little actual gambling shown in these films, so they weren’t eligible. My list also omits documentaries.
Let’s start the countdown. Part 1 includes the Best Gambling Movies of All Time — ranked 11th through 21st.
Coming next, Part 2 will include my top ten.
21. Owning Mahowny (2003)
This is the true story of the troubled Canadian banker who embezzled more than $10 million to feed his casino gambling addiction. Dan Mahowny, played by the late great Philip Seymour Hoffman, leads a double life. To those around him at home and work, he’s a respected bank manager who has almost unlimited access to cash. But in secret, he’s a high-roller on weekends who’s given all the perks by Atlantic City casinos. The predictable happens, as Mahowny digs himself deeper into debt after each visit to the casino. This well crafted drama includes John Hurt and Minnie Driver in supporting roles.
20. House of Games (1987)
Less about actual gambling and more about the art of the con and the attraction of con-artists, this movie has David Mamet’s fingerprints all over it — as both the writer and director. There are some wonderful scenes in this largely-forgotten film, which includes a non-stop array of cons — at a poker table, on the open street, at a Western Union office, inside a hotel room, and ultimately in the hearts and minds of the excellent cast of dubious characters, all led by Joe Mantegna. If you like films with twists where you’re not sure who to root for, this is a movie to see. House of Games would be ranked higher on this list except for a lackluster ending that doesn’t meet the rest of the film’s level of intrigue.
19. Oceans 11 (2001)
Most of the “Oceans” movie franchise is pretty average (one original and a trilogy of sequels). But the initial 2001 remake of the earlier 1961 “Rat Pack” classic was thoroughly entertaining and had enough twists and turns to deserve a spot on the list. The film packs a showcase of Hollywood talent — including George Clooney, Brad Pitt, Andy Garcia, Julia Roberts, Matt Damon, Don Cheadle, Bernie Mac, Elliott Gould, and Carl Reiner. The plot entails a group of Danny Ocean’s friends orchestrating a robbery of the three biggest casinos on The Vega Strip. But the story isn’t so important as the chance to see an ensemble cast having a lot of fun making this movie, filmed entirely on location. After this remake, it was pretty much downhill from there.
18. California Split (1974)
This is one of director Robert Altman’s lesser-known films. It’s never shown on television and is hard to find in its entirety. California Split is the story of two gambling pals played to perfection by Elliott Gould and George Segal. They hangout daily inside the smoke-filled Gardena cardrooms and gritty racetracks of the early 1970’s, hustling to make a buck here and there, and hoping for a big score. Their big chance comes in a high-stakes poker game in Reno, which occurs at the film’s conclusion. To its credit, California Split captures the genuine spirit and essence of the poker scene around that time. This film would be rated much higher except that the plot gets bogged down in the middle by a lot of unnecessary clutter. Altman and filmmakers should have realized all we want to see is the two stars — Gould and Segal — doing what they love to do, and that’s gambling. Had this film focused most of the time on that, and less minutiae, it might have been a classic from start to finish instead of just sporadically good.
17. Hard Eight (1996)
This is one of writer-director Paul Thomas Anderson’s first movies (Boogie Nights, Magnolia, There Will be Blood, The Master), which indicates it’s probably worth seeing no matter what. This is more of a crime thriller than a gambling movie. Most of the action takes place in Reno. Wonderful character actor Phillip Baker Hall is (shown above) in a rare leading role here, playing the part of a wiseguy gambler. He helps drifter John C. Reilly and offers to show him tricks of the gambling trade. Some of the story is implausible, but there are enough high moments to recommend the movie. Supporting cast includes Samuel L. Jackson, Gwyneth Paltrow, and Philip Seymour Hoffman.
16. Bugsy (1991)
Bio epic on the life of Benjamin “Bugsy” Siegel, who is often (mistakenly) credited with being the patriarch of what we know today as the Las Vegas Strip. Despite numerous flaws — historically inaccurate, exaggerated characters, soap opera-ish — its fun to go along for the ride, even though we know Beatty is going to end up with a bullet to the face in the final scene. The most intriguing moments involve Siegel’s building of the Flamingo Casino, and the trouble he eventually gets into with Meyer Lansky (played wonderfully by Ben Kingsley) due to massive construction cost overruns. Annette Bening is also fabulous in the role of Virginia Hill. Worth seeing.
15. 29th Street (1991)
Lesser-known movie that was overshadowed by a number of blockbuster films of this same genre (Goodfellas, A Bronx Tale, Bugsy, etc.) released at about the same time. But it’s well worth seeing. Typical New York Italian family doing all the usual stereotypical things that one would expect. However, this is the true story of Frank Pesce, Jr (played by the very underrated Anthony LaPaglia) who was the real first-ever New York State Lottery winner and the final days leading up to his $6.2 million dollar payday. Recall that New York State legalized the state lottery during the 1970’s and there was a popular frenzy surrounding that very first drawing. Gambling plays a prominent role in the film throughout. It’s also worth seeing for the fine performance by Danny Aiello, playing Frank Pesce, Sr. I’ve seen this described as a cross between Goodfellas and It’s a Wonderful Life — which tells you a lot about this overlooked gem.
14. Poolhall Junkies (2002)
Another little-known film (it flopped at the box office) that deserves much more attention. As the title suggests, this is all about shady pool halls and the art of pool hustling. Lead character’s brother gets into serious financial and legal trouble, so “Johnny” (played by Mars Callahan, who also wrote and directed the film) has to overcome the odds — not to mention the dangers of pool sharking. The various plot lines all point to an ultimate showdown, which is a game of nine-ball with everything riding on the line. Christopher Walken, Chaz Palminteri, and Rod Steiger (his last film) appear in supporting roles — but the film really belongs to Callahan himself, who masteminds pool’s very own rendition of Rocky, by writing, directing, and starring in the movie (similar to Sylvester Stallone’s similar commitment to his first film project).
13. Let it Ride (1989)
This is one of the few comedies which made the list. It’s an over-the-top camp farce about one lucky gambler and his dream day at the racetrack. None of it is believable, of course, from winning race after race after race to getting propositioned (at a racetrack!) by the drool-enticing Jennifer Tilly in one of her first memorable roles. Indeed, everything seems to be going Richard Dreyfuss’ way. No matter what he bets on, Trotter wins, and wins big. Wonderful supporting cast includes Tilly — along with Teri Garr, David Johansen, and Robbie Coltrane. This is a delightful film sure to bring a smile to your face. Don’t we all wish we could be Dreyfuss in this movie, just for a day?
12. The Lady Gambles (1949)
Few old films make the list of best gambling movies. But here’s an exception. Surprisingly well-done film about the dangers of gambling addiction, but with an odd twist — the gambler happens to be a woman. Barbara Stanwyck is excellent and thoroughly believable as a typical housewife who goes on a business trip to Las Vegas with her husband. She initially has no intention to gamble, but gradually succumbs to temptation. Shot entirely on location in Las Vegas, it’s actually one of the few existing film archives of what those early pre-Strip casinos looked and felt like (try and find film footage of the inside of Las Vegas casinos during the 1940’s and 1950’s — you can’t). For that reason alone, its a standout time capsule. This was made right after Billy Wilder’s groundbreaking classic, The Lost Weekend, which was about the dangers of acute alcoholism. It’s sort of the same thing, only about casino gambling. Way ahead of its time.
11. The Color of Money (1986)
Famed director Martin Scorcese’s long-awaited sequel to the 1961 classic, The Hustler. Paul Newman reprises his role as “Fast Eddie” Felson, this time as an aging has-been, still infected by the thrills of pool hustling. This time, he uses the young and cocky Tom Cruise as his personal pool cue, racking up bucks from unsuspected suckers in pool halls scattered all over the northeast. Beautifully filmed, excellent soundtrack, outstanding performances (Newman won a long overdue Oscar for Best Actor) — the film isn’t appreciated nearly enough by critics, due perhaps to unfair comparisons to the nearly-perfect original masterpiece. But The Color of Money has so many excellent scenes and memorable lines, that it bears seeing again and again. Only flaw is a somewhat contrived ending. Here’s one of the movie’s most memorable scenes with Paul Newman and Forest Whittaker in one of his early film roles. We’re so used to seeing the con played from the hustler’s side, but here’s the other perspective. This scene perfectly captures the essence of the hustle, including not just money lost, but the angst being humiliated.
Note: I have seen each of these movies. However, one additional film probably belongs in the top 21. It’s a rare 1989 film made in Hong Kong starring Chow Yun Fat called “God of Gamblers.” This movie gets very high ratings. But I have not seen it, so cannot comment.
COMING NEXT: THE TOP TEN GAMBLING MOVIES OF ALL TIME