Top 10 Greatest Gambling Movies Of All Time

Mar 15, 2013; Las Vegas, NV, USA; General view of the Mandalay Bay hotel and casino on the Las Vegas strip. Mandatory Credit: Kirby Lee-USA TODAY Sports

This is a guest post from our friend, Motown Fisher. Fisher works with FanSided and Pro Computer Gambler on betting guides.

I have seen A LOT of movies and read A LOT of books about gambling, some are clearly better than others. Some inspire me, some motivate me, and some are just fun to watch.  These are “The Nuts” of gambling movies that occasionally move around in sequence, but generally, to this point as a pretty solid list there are generally few movies made well within the genre.

Here are my top 12 (With 7 unordered honorable mentions) movies about gambling of all time. They are all very different from each other reflecting the spectrum of all sorts of gambling stories, and at least 3 of them probably aren’t on too many lists. Mostly because Top 10 lists are filled with “standard” crap to get the search engines to their page. Not mine.

Honorable Mentions:

National Lampoons Vegas Vacation (1997) – I have seen this movie, or at least parts of it, so many times I’ve lost count (Although I think it’s probably over 20 right now) … It’s the clear lighter side of gambling, and hosts one of the top 10 scenes of all time when Chevy Chase and Randy Quaid walk into the Hillbilly Casino desperate for a win.

Tilt (2005) – This was a cheesy, but nicely made series (ok it’s NOT a movie, sue me) by ESPN of just 9 episodes. General shady poker lifestyle plays the central theme. Michael Madsen is the World Poker Champion and resident bad guy, and steals the show with the character of “Don Everest”. Chris Bauer (Sheriff Bellefleur of True Blood) also plays a central figure chasing Madson.

21 (2008) - Truth is I HATED this movie… Ok HATE is a strong word, but I HATED the last, oh, 35 minutes or so before the credits. The reason I even mention it – is because it’s a blackjack movie based on a book which is a clear top 10 gambling book called “Bringing Down the House: The Inside Story of Six MIT Students Who Took Vegas for Millions”… And of course, just on its own merit, Kevin Spacey, is well, standardly brilliant. For the MOST part, the movie does a great job telling the story of the characters and their actions, until the last act, where it becomes total Hollywood bulls*it. Book is great though (Did I mention this)…

The Color of Money (1986) - Some think this movie is better than “The Hustler”, I just think it’s more recent… great show, but not as great as the 1961 version, but obviously good enough to get a mention. Tom Cruise is Vincent, protégé of Eddie, the same character in the Hustler. I saw this movie first in life, but as mentioned, if you haven’t seen the original, you’re missing out.

Big Hand for the Little Lady (1966)  Just a cute, fun, spaghetti western style poker movie starring Henry Fonda, and Joanne Woodward. A little (a lot) over the top, but it’s nearly 50 years old so it gets a pass for just existing.

Cincinnati Kid (1965)  I’m sure some are already insulted it’s not in the top 5. I liked it, alot, Steve McQueen was great, and much respect to it as a gambling/poker movie that came out LONG before the The Sting, and really, MOST good gambling movies. But in many ways, it’s like comparing Babe Ruth, to Derek Jeter. Let’s just say it was good, but in a different time, and for different reasons.

Two For the Money (2005)- Generally wasn’t well received, but McConaughey is brilliant as is Pacino (as usual) as the mentor. Best scene is the 2 of them at a G.A. Meeting.  It tells much about the world of sports betting, and “touting”.  Not many good movies on sports betting out there, but this is at least one of the better ones that got its story told.

Top 5

5) The Hustler (1961) – One of, if not THE original Gambling movie. Paul Newman is Eddie, a pure pool shark degenerate who doesn’t care about money as much as winning, and showing everyone he’s the best pool player in the world. The movie is in Black and White, which just adds to the “old school” effect (Assuming a movie over 50 years old really needs to add more “old school” effect) … I’ve seen this movie a half dozen times, and the final scene with “Fats” is maybe one of the greatest gambling scenes of all time.

4) Rounders (1998) – If this isn’t on a top 5 of EVERY PERSON who has EVER gambled a nickel in the past 15 years, they are clearly living under a rock, or just ridiculously stubborn. Its theme is poker, and mostly the underground variety. Matt Damon, and Ed Norton are supported (yes supported), by an all star case including John Malkovich, John Turturro, and Martin Landeau. This movie was pretty much, next to Chris Moneymaker winning the World Series, one of the keys to the poker boom of the past decade or so.

3) The Sting (1973) – A bona fide classic! Paul Newman (for a third time on this list) and Robert Redford are a couple of con men who get involved in every sort of con under the sun. Poker and Horse Racing are the central themes. I saw this movie in my teens, then I saw it again in my 20′s, and then my 30’s and man did it hit me how good this movie was after I really got to understand it more as I got older. It also won Best Picture that year – a lot of times that’s good.

2) Owning Mahowny (2003): Another on few peoples lists, as it’s essentially a degenerates soliloquy. Philip Seymour Hoffman is a pure degen who at one point takes, “all the home teams in the AL, and all the road teams in the NL”, or something to that effect. Of course, this was all after he wrote large sums of bum loans as the loan manager of a Canadian bank. The show is “castaway” for gamblers, Hoffman owning about 92% of the lines throughout the movie. Very dark, very deep – extremely worthwhile.

Current #1

This changes from time to time, but this is one of the most fascinating stories of all time to hit the theater, if indeed, it actually ever hit it.  I have chosen 2 very dark movies as my top 2, because these are the real stories of real people. The “truth” in gambling, is far more fascinating to me than fictional accounts, or made up versions of how gambling works.  

High RollerThe Stu Unger Story (2003) – Here’s one guaranteed NOT to be on many top “anything” lists.  Stu Ungar was a crazy degenerate caught up in the only world he knew. He was also without question the best Rummy player in the world, and, many argue, the best poker player that ever lived winning back to back titles (’80 & ’81), and winning a third in 1997 after living an incredibly hard life in between.

I’m not old enough to have seen, or known about Stu until well after his passing, but “The Soprano’s” Michael Imperioli puts in a great performance in telling us how even “successful” gambling has a price. I’ve probably seen this movie over 25 times, as it’s incredibly deep and thought provoking, but also extremely dark, and cautionary. Not many movies in this genre can give me goose bumps, or bring a tear to my eye, but this one has on more than one occasion.

Topics: 21, High Roller: The Stu Unger Story, Movies, Rounders, The Hustler, The Sting

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