Top 5 Winner-take-all Movies

If you are looking for motivation to be a better gambler, or even just to try and avoid the lowest of lows


In this 1998 instant classic, we learn about reforming and getting our vices under control. Or perhaps we discover that you can’t quit poker. The character dynamics in this movie between Matt Damon, Ed Norton, and Gretchen Mol fantastic.

Mike McDermott promised his girlfriend that he was done with poker. But his buddy, Worm (Lester Murphy) calls him back into the life of backroom, underground poker games to help him grift mob affiliated high-rollers. Matt McDermott (Matt Damon) needs college money, so; he reluctantly consents to Ed Norton’s character. Broken promises and the dangers of hustling the mob; that’s what this flick is all about.

There were rumours abound that this is unofficially based on the life of Norm McDonald before he made it as a comedian and actor. Those rumours have been squashed, but the story is still connected to the Norm in the eyes of many. So, what’s the moral of the story? I guess it’s that if you want to win gobs of money playing poker, cheat.

Lay the Favorite

A Florida stripper moves to Vegas to seek an honest living as a cocktail waitress … need I say more? Ok. So, Beth (the stripper turned cocktail waitress) moves to Vegas and meets Dink, a professional gambler who employs runners to lay big bets.

As it would turn out, Beth has a mind for numbers, starts learning about sports betting and how the pros do handicap but Dinks wife doesn’t like their dynamic and makes Dink fire Beth. Later, she moves to NY, where sports betting is illegal, and later helps to set up a legal operation down in Curacao.

Chaos ensues and after drugs, hookers, bad beats, and possibly Feds, another gambler, Dave Greenburg, is in significant debt. Long story short, they get inside info on a basketball game and lay it all on the line. Everyone gets the money they need to clear their debts and get back into the black.

So, what did we learn from this movie? Again, I think the moral of the story is to cheat.

High Roller: The Stu Ungar Story

If you play poker, you have probably heard of Stu. In this bio-epic, you see the ups and downs of high-stakes poker through the eyes of one of the best. One minute a millionaire, another moment completely broke, we can learn a lot from Stu’s mistakes.

The moral of this story is gambling can negatively impact your life if you are addicted to it, no matter how good you are. Also, if you are good at poker, don’t bet horses.

The Cincinnati Kid

I remember hearing once a kid to never play cards with anyone named after a city. Steve McQueen plays Eric Stoner (Cincinnati Kid), who is an up and coming poker player that wants to beat the best players and earn the title of best poker player in town. However, he finds out that an upcoming game is fixed but refuses to cheat, deciding that he’s skilled enough to overcome the fix.

This is a great film all around; I mean, it’s Steve McQueen. Finally, the moral of the story of this one is cheating is bad, mmkay.


You may or may not remember this 1994 Western starring Mel Gibson, Jodie Foster, and James Garner. Maverick (Mel Gibson) is a pro card player who needs three thousand bucks to enter into a winner-take-all poker tournament. I’m not sure where they got that number, but by today’s standards, that’s roughly a $76,000.00 buy-in. Anyhow, he teams up with Jodie Foster and James Garner to get his buy-in for the big river-boat game.

This one is like Butch Cassidy crossed with Lethal Weapon. The moral is something like if you are willing to play card games for thousands of dollars with a bunch of low-lives with guns strapped to their hips, be smart enough, and tough enough to keep your winnings.