The 21 Best Gambling Movies of All Time (1-10)

In PART 1, I posted the first half of my list — “The 21 Best Gambling Movies of All Time.”

READ HERE:  THE 21 BEST GAMBLING MOVIES OF ALL TIME (11-21)

Continuing with my countdown, let’s proceed to the top ten:

10. The Killing (1956)

This was an early Stanley Kubrick film made in 1956.  It’s about a scheme to rob a racetrack (filmed on location at Santa Anita).  Very dark film with some humorous moments.  Also quite troubling, since the plan calls for a sniper to shoot one of the racehorses while running down the backstretch and in the ensuing chaos, the racetrack gets robbed by masked gunmen who take $2 million in a heist.  The plot hits a little too close to home given some current events.  Still, if you can overlook its darker edges, The Killing is a very good movie.  Sterling Hayden plays the grizzled unsympathetic lead.  The wonderful surprise ending is not to be missed.

9.  Big Hand for a Little Lady (1966)

This is one of three comedies to make my top 21 list.  Not much should be taken seriously in this movie about a high-stakes poker game held in the backroom of a saloon in Laredo, Texas.  What makes this movie so special are outstanding performances all around by Joanne Woodward, Henry Fonda, Jason Robards, Kevin McCarthy and other supporting actors in addition to some surprising plot twists along the way.  Henry Fonda gets involved in a big poker game way over his head with his family’s life savings.  In what is about to become the biggest poker hand of his life, he suffers a heart attack.  So, his wife (played by Woodward) fills his seat at the poker table, even though she has no clue how to play.  The dialogue is fun and witty making for what’s become an old-fashioned classic.  The final hand lasts about 30 minutes and is a joy to watch from start to finish.

8.  Rounders (1998)

Some poker players rank this film higher.  It’s a pretty good movie, but not as strong as the far more creative (and sometimes edgy) collection of films ranked higher on my list.  Matt Damon plays a New York City college student who discovers a natural talent and intense passion for poker playing.  Trouble is, he’s weighed down by the baggage of a deadbeat friend appropriately named “Worm,” played by Ed Norton, Jr.  Virtually every poker friend I know has seen this movie, so I won’t spend much time revealing much about the plot.  New York’s underground card clubs during the 1990’s are portrayed with remarkable accuracy in this film (some of the characters were based on actual people who worked inside the clubs).  My strictly personal biases against this film include a failure to buy into Damon as a true poker professional and the wildly exaggerated bad-guy characters played by John Malkovich (“Teddy KGB”) and the thug who threatens to beat up Damon throughout the movie.  Best two performances are John Turturro and Martin Landau.  Stands up well over time as a good movie.  But it’s nowhere near the best.

7.  Lock, Stock, and Two Smoking Barrels (1998)

Writer-director Guy Ritchie’s masterful film caper about a band of Brits who get cheated in a card game (brag).  They owe half a million pounds to the London East End mobster and have only a week to come up with the money.  They resort to a wild scheme of robbing and stealing in order to satisfy the debt and from there things really spin out of control.  Cleverly written and paced, with the typical stylish flair one would expect from Ritchie’s direction.  Story enhanced by an excellent soundtrack of catchy songs.  Widely successful in the U.K., but not nearly as well-known in the U.S.  A must-see if you like tough guy movies with lots of memorable insulting street dialogue, which is often downright poetic.

6.  The Pope of Greenwich Village (1984)

This is perhaps Mickey Rourke’s very best film role, but his sidekick Eric Roberts steals the show.  The quintessential buddy movie, Rourke and Roberts struggle to make ends meet in New York’s Little Italy.  So, they resort to doing something really stupid — stealing from the mafia to make some quick cash.  Along the way, Roberts receives inside information about a horse race.  So, they head off to the Monmouth Park racetrack in New Jersey to bet on his “sure thing.”  The Pope of Greenwich Village has some wonderful moments and is filled with outstanding performances.  Two of the very best are by Geraldine Page in her final film role and the always-fabulous Burt Young, who plays Mafia don, “the Pope.”  Rourke is also perfect in a memorable performance reminiscent of the charisma and toughness embodied James Dean.  When I saw this right out of college, everyone I knew wanted to be just like Mickey Rourke.  Might be criticized for inclusion on the list as not a true gambling movie, but there are enough elements for me to include it on the list.  Here’s the trailer, which gives a nice overview:

5.  The Cincinnati Kid (1965)

For those who mistakenly think Rounders is a better movie, here’s an assignment.  Watch the two climactic final scenes and then admit which one is far superior.  In fact, just about everything about The Cincinnati Kid is better.  That’s why this film gets ranked near the top of the best gambling movies ever made, despite some admitted flaws — including the implausible final poker hand (mathematically speaking).   Steve McQueen plays the title role as the “Cincinnati Kid.”  Edward G. Robinson is cast as “Lancey Howard” — also known as “The Man” in poker circles.  McQueen’s ambition is to beat the man, but he wants to do it honestly on his terms.  Although he’s given the chance to cheat and win, McQueen does the honorable thing and is determined to prove himself as the new titan of poker.  The Cincinnati Kid is a boldly accurate portrayal what the high-stakes gambling subculture must have resembled during the 1930’s.  It also shows poker as a respectable (and even noble) pursuit.  The movie is helped by a hand-picked cast of brilliant supporting actors — Karl Malden, Tuesday Weld, Rip Torn, Jack Weston, Cab Callaway, and Ann Margaret.  Back to the amazing final scene:  Why does this stand above all the others?  Pacing.  Texture.  Timing.  Musical accompaniment.  Intensity.  It begins so slowly, so innocently — just as real poker hands do.  As each card is dealt, the room full of people — each linked to the outcome in different ways — becomes more intense.  Those watching begin projecting their own hopes, desires, and suspicions upon the hand and the game.  The hand plays out to a gut-punching conclusion, filmed to absolute perfection.  An amazing cast.  A brilliant movie.  A thrilling conclusion.  This stands as the best poker movie of all time and perhaps the single best scene ever filmed.  Here’s a collage of scenes to the title theme song, performed by Ray Charles.  Hey, when Ray Charles sings the theme, that’s an instant classic:

4.  Casino (1995)

Director Martin Scorcese is in all-too-familiar territory here with his usual ensemble cast of badasses, which includes Robert De Niro and Joe Pesci as the stars.  Sharon Stone also delivers arguably her best performance.  Based on the true story of “Lefty” Rosenthal and the Argent Corporation scandal which engulfed the now demolished Stardust Casino back during the late 1970’s, the plot essentially depicts the decline of organized crime in Las Vegas (and the subsequent rise of something far worse — big corporations).  Watch this brilliantly-filmed scene shot in the desert where Joe Pesci gives Robert De Niro a lecture filled with F-bombs:

3.  The Sting (1973)

The Sting is a timeless classic.  It won seven Academy Awards, including Best Picture in 1973.  It’s the story of a small group of grifters in Chicago during the Depression who pull off an elaborate hoax on an underworld boss played wonderfully by Robert Shaw.  Paul Newman and Robert Redford are the heroes.  They manage to hire a crew con-men and pull off the best and most authentic scam in movie history which uses a now-familiar past-posting technique in relation to the reporting of horse racing results.  The musical score by Scott Joplin (arranged by Marvin Hamlisch) sets the mood perfectly.  Everything works to perfection in this film directed by the late George Roy Hill (Butch Cassidy and the Sundance Kid, The World According to Garp).  Arguably could be number one on the list.

2.  The Gambler (1974)

Actor James Caan doesn’t receive nearly enough credit for a stellar film career filled with memorable roles and fascinating movie characters.  This performance, among his very best, is often overlooked and largely forgotten by the critics and the public alike.  Caan plays a NewYork University professor hopelessly hooked by the thrills of living on the edge.  He engages in all forms of gambling but gets into deepest trouble by sports betting.  The film shows his gradual self-destruction and psychological deterioration to the lowest depths of depravity.  What makes this rarely-seen movie so special is just the right intensity Caan brings to a very demanding film role.  I’m not sure any other actor could have portrayed the “Axel Freed” character quite in such a believable manner.  Every frown, grimace, and fist-pump is performed with just the right volume.  Yet, for all his character flaws, Caan also manages to make us care to the point where we cheer for him.  This gem, now 45 years old, might seem a little dated to some with its 1970’s fashions and street lingo.  But beneath the tight flashy shirts and wide collars, the script and film combine for an astonishingly powerful and accurate depiction of the pitfalls of compulsive gambling.  It also includes a number of humorous moments, where Caan goes to ridiculous extremes to get the latest sports scores (this was long before ESPN, the Internet, and cell phones when scores were harder to come by).  Everything in this movie rings true.  It’s probably the most realistic movie about (the downside of) gambling ever made.  I give it the nod above many other outstanding films because it’s so edgy and doesn’t resort to sentimentalizing the serious subject matter.

Note:  This is the original, not to be confused with the 2014 remake starring Mark Wahlberg, which is terrible.  READ MY SCATHING REVIEW HERE

The Gambler deserves multiple film clips.  The first is a collage of references to Dostoyevsky’s literary classic of the same name:

The second scene shows Caan so desperate for cash that he’s forced to borrow $15,000 from his mother.  Watch Caan pulverize the prickly bank teller, played by James Woods in one of his earliest film roles:

The third scene is interesting because it shows the psychological high of compulsive gambling.  Most films on the subject only show the downside.  To The Gambler’s credit, we are able to understand that gambling provides insatiable satisfaction when winning.  Watch the brilliantly filmed blackjack scene at Caesars Palace towards the end of this clip:

1.  The Hustler (1961)

More than 50 years after it was released, The Hustler still stands an absolute masterpiece.  Brilliantly written, perfectly filmed, and utterly believable from start to finish, the plot evokes meanings and messages right out of a Shakespeare tragedy.  Paul Newman plays a brassy young pool shark who desires to be the very best at the game.  To prove he’s the best, that means there’s only one man left to beat — the legendary Minnesota Fats.  The movie opens with an overnight pool showdown between “Fast Eddie Felson” and “Minnesota Fats.”  The outcome of the game sets up the remainder of the movie and another game of revenge.  Normally, it would impossible to outshine Newman’s utterly convincing performance as the character we both love and loathe.  But George C. Scott, playing the role of Felson’s business manager and backer manages to do so, along with Jackie Gleason, perfectly cast as “Fats.”  This film was daring for its time, for many reasons.  First, it showed the immensely popular Newman in a less than a heroic role.  It also violated usual typecasting, by using one of the era’s most famous television comedians (Gleason) playing the part of the heavy.  Then, George C. Scott was also relatively unknown at the time and is critical to the plot.  Moreover, The Hustler portrays gambling as it was in those days, a gritty vocation with immense personal risks and costs.  Perhaps what really makes this movie rise above all the rest are its immortal words and ideas.  The very best is delivered in the bar scene when Scott meets Newman officially for the first time and tells him it’s not talent that matters — one’s character is far more important.  That might be the single most poignant message to remember for any gambler.

So, what movies did I miss?

Here’s a look at several well-known (and some less well-known) films that missed the cut.  These movies are listed alphabetically:

Movies That Didn’t Make the List:

The Big Town — 1987 drama staring Matt Dillon.  The star moves from a small Midwestern town to Chicago to become a professional craps shooter, playing (and winning) in mob-run joints.  Yeah, right.

Casino Royale (1967) — Touted as a comedy spy thriller with an all-star cast, this an unwatchable film.  I’ve never made it all the way through without falling asleep or changing the channel.  Mind-numbing dullness.

Casino Royale (2006) — This was Daniel Craig’s first film as James Bond.  I have heavy personal baggage with this movie since I witnessed some of the atrocious business practices by the owners of the James Bond franchise.  Admittedly, that gave me a very sour impression of this movie and I couldn’t enjoy it.  Bond movies now have little to do with art and entertainment.  It’s a cash cow, and nothing more.

The Cooler — Story about a supposed “cooler” hired by a casino to bring bad luck to hot gamblers.  Some critics liked this movie.  I didn’t.  It might have made for a fun caper had the idea of a “bad luck charm” been scripted with Jim Carey playing the lead.  Imagine the possibilities.  Instead, the usually wonderful William H. Macy plays the house iceman, and the plot inexplicably takes a darker twist.  Moreover, I wasn’t buying for a minute that hot cocktail waitress Maria Bello would fall for the hopeless loser played by Macy.  Filmed on location in Downtown Reno, which is supposed to substitute for the real Las Vegas.  That should tell you everything about its authenticity.

Croupier — is a British-made film which launched Clive Owen’s career as a leading man.  Owen plays a casino (roulette) dealer.  The film shows the darker side of London’s gambling scene, which pales in comparison to the way gambling is often portrayed in America, particularly Las Vegas.  Perspectives are unusual in the sense that we see the casino subculture from the perspective of a dealer, rather than a player.  The contrived story isn’t as important as the rather accurate depiction of casinos and much of the attitude behind the scenes by those who work in the business.  The most revealing scenes are those which capture the repetitive dullness of casino gambling over time, behind the allure of glitz and glamour.  Indeed, all that glitters is not gold.

Deal — Another film where I was on location and witnessed some of the filming, which took place in New Orleans.  This movie is painful to watch.  Laughingly bad in parts.  Burt Reynolds stars and a bunch of professional poker players play themselves in this dreadful movie that the Las Vegas Review-Journal film critic described as follows:  “Deal makes Lucky You look like Citizen Kane.”

Diggstown — Somewhat unknown movie released 1992 about boxing and taking a fall for money.  This film came close to making the Top 21 cut.  Stars James Woods (who deserves a lifetime achievement award for appearing in more films on my list than any other actor, except Paul Newman) along with the Louis Gossett, Jr.  Decent, but nothing memorable.

The Grand — Spoof about a big-time poker tournament.  Tries to copy the cult following of the Christopher Guest “mockumentaires” (This is Spinal Tap, Best in Show, A Mighty Wind) which mocks real-life people and events, but fails to really connect or inspire much of a reaction.  To be fair, there are a few hysterical scenes in this movie.  But most of the film is a bore and a monumentally missed opportunity.  Note that just before this film came out, I contacted Christopher Guest to try and get him to do a spoof on the WSOP.  He responded by noting that this film was already in production.  The end result is a huge disappointment.

Guys and Dolls — Fabulous musical, but a mediocre movie — despite the stellar cast that includes Marlon Brando, Jean Simmons, and Frank Sinatra.  What kills the movie is the contrived movie set.  Had this actually been shot on location out in the streets of New York, it would have had much more color, character, and energy.  Imagine Sinatra really singing his part on a busy day out in the middle of Times Square.  Instead, this 1958 film comes across as little more than a lame high school musical.

Havana — Robert Redford is cast as a professional poker player in Cuba right before Castro comes to power.  For movie audiences hoping for more of the same energy that worked so well in The Godfather II (recall the famous “I know it was you, Fredo!” scene), there’s little of that intrigue here despite an eclectic array of characters who manage to prosper in Havana amid rampant corruption.  A distracting story of a love triangle does little to maintain our interest.

High Roller:  The Stu Ungar Story — I’ve never commented publicly about this film.  Director A.W. Vidmer was kind enough to list me in the film credits, so my comments are a clear conflict of interest.  For such a small-budget film, Vidmer made a watchable movie.  But Michael Imperioli is horribly miscast in the lead role.  This movie never really captures the magnetism and mysticism of Ungar, in my (biased) opinion.

Honeymoon in Vegas –– Nicholas Cage has some funny moments playing the usual exploding human pressure cooker for which he’s become typecast.  An enjoyable movie which includes an amusing poker game scene with Cage, James Caan, and former UNLV basketball coach Jerry Tarkanian as one of the players.

Indecent Proposal — Robert Redford offers a couple $1 million if he can go out on a date with the guy’s girl, played by Demi Moore.  When it was released, this film sparked millions of arguments from couples bickering about what they would do if offered the same proposition.

Kaleidoscope — 1966 British film that sounds interesting, staring Warren Beatty as a professional gambler.  He breaks into the factory that makes all the playing cards at European casinos and manages to mark the decks.  Interesting possibilities.  But I have never seen this film, so I can’t include it on the list.

Lay the Favorite — How did filmmakers manage to blow this one?  Filmed in entirely on location in Las Vegas and New Orleans a few years ago — starring Bruce Willis and Catherine Zeta-Jones about a woman who becomes immersed in high-stakes sports betting.  I saw parts of the filming in both cities and expected this to be a huge hit.  The movie lasted about a week in theaters and was blasted by critics.  It must have been awful, but I admittedly have never seen it

Lucky You — Released in 2007 about a professional poker player in Las Vegas played by Eric Bana.  Also stars Drew Barrymore and Robert Duvall.  Contrived, predictable, and pretty lame.  Reportedly cost $55 million to make and earned a paltry $8 million — making it one of the most disastrous films of that year.  This pretty much killed off poker movies during the boom years.

Maverick — Innocent fun at times, but an absurd final scene where everyone is dealt a monster hand keeps this off the list.

Molly’s Game — Aaron Sorkin’s directorial debut is well above average and far better than the book (though film is fabricated in several instances).  Jessica Chastain and Idris Elba carry the movie, which probably belongs in the Top 20, despite some glaring flaws.  READ MY REVIEW HERE

Oceans 11 (1960) — Original Rat Pack flick that set a trilogy into motion some forty years later.  Great ending and some interesting scenery of Las Vegas at the time, but the movie drags far too much to make the list.

Shade — Quickly forgotten bomb starring Sylvester Stallone released in 2003 about the set up of a crooked poker game.  I have not seen this, but it apparently received generally positive reviews.

Two for the Money — Mind-bogglingly awful film starring Matthew McConaughey as a sports gambling tout, along with Al Pacino and Rene Russo.  Supposedly based on the true story of scumbags who hustle “picks” on games.  This movie is ludicrously bad and painful to watch.  One of the worst gambling movies ever made.

21 — The filmmakers somehow managed to make the true story of the MIT Blackjack Team into a bore.  Poorly miscast lead character and a largely unsympathetic cast transforms this from a movie where we cheer for the card counters to succeed into hoping they get caught.  And “Mr. M” is much nicer in person than the jerk portrayed by Kevin Spacey.  Hugely disappointing.

Vegas Vacation — Many funny moments.  But not nearly as good as two other “Vacation” films in the National Lampoon series (Vacation and European Vacation).  Worth seeing for a few laughs, but not top-21 material.

Note:  “If you enjoyed this best gambling movie countdown, be sure to check out these 99 Insanely Interesting Gambling Movie Facts You Probably Didn’t Know”

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