Ranking The 5 Best Gambling Movies Of All Time.

Everything and everyone has a perfect fit. Peanut Butter has jelly, Kobe had Shaq, and so on. What’s a movie’s perfect fit? If it involves gambling!

The hardest part about this blog? Figuring out how to cut this list down to 5 movies. So many movies deserve to make this list, but only 5 are able to.

Did I get my list right? If not what movies did I leave off the list?

Here’s my ranking of the 5 best gambling movies of all time.

5. Uncut Gems (2019)

Adam Sandler, Julia Fox, Kevin Garnett? How can you not love this movie? Adam Sandler has always been one of my favorite actors, mostly because of the comedy movies he has starred in. This movie isn’t your typical Adam Sandler movie but his performance was a perfect 10/10 for what this movie needed.

Basically, it’s just about Adam Sandler trying to chase that one big win to pay off his debt. Even if you’re not a degenerate, the sheer thrill of watching The Sandman watch a basketball game trying to hit a parlay will give you so much life you’ll become immortal. If you haven’t seen this movie you need to. If you have seen it, consider this is a reminder that it’s been too long since you have seen it last (myself included).

Every true gambling addict uses this line many times.

4. Rounders (1998)

FUCK, I hate putting this in the 4 spot… But I have to. Rounders is starred by my favorite actor of all time. Matt Damon. All his movies from the late 90’s early 2000s are must-watch. Including Rounders a movie, all circled around the best game in any casino. That’s right. Poker.

What’s The Movie About?

It’s about a man (Matt Damon) who loses everything he has in a big poker game and decides to quit playing poker (thanks to his GF). When he reunites with an old buddy he quickly gets sucked back into the lifestyle which is where this movie starts taking off.

Matt Damon delivered in this must-see poker movie. Even if you know nothing about poker this movie is still a must-see if you haven’t seen it already. The opening scene will suck you in instantly.

3. Mississippi Grind (2015)

Ryan Reynolds best movie he’s been in and the gap isn’t close. If you’re laughing at that take right now google his best-ranked movies and guess what movie sits at the top? Yup, you guessed it “Mississippi Grind”. A movie I accidentally came across years ago has turned into one of my favorite movies.

It’s a movie about two men who embark on a road trip filled with gambling stops on the way all because one of them thinks the other is a “good luck” charm. All these movies deliver by showing you the highs and lows of gambling but this one shows it like no other IMO.

A movie that I feel never got the respect it deserved. When people are talking about great gambling movies this movie never is mentioned.

Ryan Reynolds and the rest of this cast make this a top gambling movie.

2. Mollys Game (2017)

It was painful putting Rounders at 4. Putting Mollys Game at #2 is actually a different level of pain. It’s another Poker movie, but this one is based on all the real events of “Molly Bloom”. A girl who was a shrub away from being in the Olympics quickly turned into the “Poker Princess”. Hosting home games for BIG Celebrities for numerous years, coast to coast.

Watch this movie at least two times. Watch it normally the first time. After go to google & look up who the actors are portraying from the real-life poker game.

There are plenty of names on the list. ^{(spoiler alert in that link)}

According to Molly Bloom, there are plenty of people left off the list because she didn’t want to ruin people’s careers. She only decided to talk about the people who had been linked in the federal subpoena given.

Really makes you wonder about the things she saw, the drugs she saw people do, and the “blackmail” she holds against people. Insane.

Molly’s Game shows you the side of the Poker world that is completely legal and happening all around the world every day… At all times. “HOME GAMES“.

Watch this clip to see what Molly did to get ready for her first home game.

10/10 Movie, And A MUST WATCH for EVERYONE.

1. 21 (2008)

If you’re ever on a plane going to Vegas, this is the only movie that should be on ur screen. Yes, ur, not some MIT Nerd who can solve every equation in a matter of seconds. But you are that guy just like all those students who were sitting on the plane dreaming about all the money you’re going to win at the tables that weekend. The difference? Those kids were winning more money then they knew what to do. Our dream was their reality. That’s what makes this movie ranked atop the list.

This movie is a straight classic gambling movie. My 4 other movies are popular movies, but I wouldn’t blink twice if someone told me they haven’t seen them. 21 on the other hand? I’ll 100% be blinking twice. It’s another movie based on a real story about 6 MIT students who are trained to “Bring Down The House” by their ability to count cards.

Whats Counting Cards?

Card counting is a blackjack strategy used to determine whether the player or the dealer has an advantage on the next hand. Card counters are advantage players who try to overcome the casino house edge by keeping a running count of high and low valued cards dealt.

It’s not illegal by any means, the casinos just highly frown upon it. With all the cameras in today’s day it’s way easier to get caught… but also a lot harder for the casinos to “teach you” why not to do it. When this movie was taking place it was the complete opposite. Harder to get caught, but if you did well, start running and pray to god you don’t get caught.

Another movie that I can watch on repeat and never get sick of. The book gives you 100x more details and is also a must-read.