Greatest Gambling Movies of All Time March Madness Tournament Bracket

March is simply the best time of the year. The sun is beginning to shine brighter, the days start to get longer, and college basketball throws out the best tournament of the year—March Madness. The single-elimination format simply makes everything so much more exciting. Imagine if all of life’s important decisions could be decided through a March Madness-like tournament. Where to have dinner? What car to buy? What girl to date? Life would be so much easier.

However, there is one area where we can actually make an important decision by having a March Madness tournament—movies. The ATS blog could talk for days on end about films, but just don’t get us started on Tom Cruise, we can’t stand him. But, since it is March, let’s use the single-elimination format to decide one of life’s pressing questions—what is the greatest gambling movie of all-time?

The Rules: I am going to compile a list of the eight gambling movies I consider to be the best. In order to make the tournament more official, I will be seeding them by their IMDB rankings.

The movies:

1) Casino

IMBD Rating: 8.2

IMBD Synopsis: “Greed, deception, money, power and murder occur between two mobster best friends and a trophy wife over a gambling empire.”

2) The Hustler

Rating: 8.1

Synopsis: “An up-and-coming pool player plays a long-time champion in a single high-stakes match for money and pride.”

3) Casino Royale

Rating: 7.9

Synopsis: “Secret Agent James Bond sets out on his first mission as 007 and must defeat a weapons dealer in a high-stakes game of poker at Casino Royale.”

4) Rounders

Rating: 7.3

Synopsis: “A skilled, but reformed, gambler must return to playing big stakes poker to help a friend pay off loan-sharks.”

5) The Cincinnati Kid

Rating: 7.2

Synopsis: “A young brash poker player tries to prove himself in a high-stakes matchup against a legendary seven-card stud player.”

6) Owning Mahowny

Rating: 7.0

Synopsis: “A bank manager with a gambling problem and access to a multi-million dollar account begins funding his addiction through bank fraud.”

7) The Gambler

Rating: 7.0

Synopsis: “A literature professor gets in deep with the sharks after borrowing from his girlfriend and stealing from his mother to feed his gambling addiction.”

8) 21

Rating: 6.7

Synopsis: “The fact-based story of six MIT students who were trained to become experts in card counting and took Vegas for millions in profits.”

Elite 8

1) Casino vs. (8) 21

And the winner is: ‘Casino’ is a Martin Scorsese classic that is hands down the best film on this list. DeNiro and Pesci give an acting tour de force, and are simply amazing in the film. The only trouble is that ‘Casino’ is more of a gangster film than a gambling film. The Kevin Spacey led ‘21’ is a very entertaining gambling movie that highlights the absolute fun of playing blackjack. There was almost an upset, but ‘Casino’ pulls it off and advances to the next round.

Winner: ‘Casino’

2) The Hustler vs. (7) The Gambler

‘The Hustler’ is one of the highest rated movies of all-time and stars the legendary Paul Newman as a fast-talking pool hustler. The film is a modern classic and has more than a few excellent pool scenes. ‘The Gambler’, on the other hand, is a tale of a degenerate gambler who also happens to be a literature professor teaching a class on a Fyodor Dostoevsky’s literary masterpiece by the same name. The film goes deep into the life of a gambler with an uncontrollable sickness, and is an excellent character piece. Both films are great gambling movies, however, ‘The Hustler’ is simply too smooth to be eliminated in the first-round.

Winner: ‘The Hustler.’

3) Casino Royale vs. (5) Owning Mahowny

And the winner is: ‘Casino’ Royale was perhaps one of the best Bond films since Sean Connery donned the suit and tie. The movie was filled with action, a surprising amount of quality gambling scenes, and best of all, a dude with a bleeding eye. ‘Owning Mahowny’, for those that haven’t seen it, is masterful film about a banker who becomes addicted to sports betting and blackjack, and begins funding his addiction by committing bank fraud. The subject matter is a bit depressing, but the movie it self is fantastic. This is a matchup that could have gone either way, but ‘Owning Mahowny’ is too good of a film to not advance to the next round.

Winner: ‘Owning Mahowny’

4) Rounders vs. (5) The Cincinnati Kid

And the winner is: This is a matchup that could have been saved for the finals, if the seeding had turned out differently. Both of these movies are held in the highest esteem by two different generations of gamblers. ‘The Cincinnati Kid’ may be the smoothest character in cinematic history, and Mike McDermit is not far behind. Both movies have excellent gambling scenes, great acting, and a stellar poker showdown to end the film. This is a great matchup that comes down to the final possession, but the Cincinnati Kid takes it.

Winner: ‘The Cincinnati Kid’

Final Four

1) Casino vs. (5) The Cincinnati Kid

In the biggest upset of the tournament, ‘The Cincinnati Kid’ eliminates the number one seeded ‘Casino’. The movie is just too good to lose.

Winner: ‘The Cincinnati Kid’

2) The Hustler vs. (5) Owning Mahowny

‘Owning Mahowny’ had an excellent run, but ‘The Huslter’ is too great of a movie to lose in the Final Four—Paul Newton is simply excellent in his role.

Winner: ‘The Hustler’


(5) The Cincinnati Kid vs. (2) The Hustler