15 Must-See Movies about Winning Money

One of the things I enjoy is a good movie about winning money. And although these types of movies are usually entertaining, there really aren’t that many gambling movies, or movies about people who win money.

Here you’ll find 15 of my all-time favorite movies about winning money.

Lottery Movies

1. It Could Happen to You

In It Could Happen to You, Charlie Lang, a New York cop with a heart of gold, wins a share of the lottery. However, the day before, having been caught without enough money to tip waitress (Yvonne), Charlie offers her half the winnings.

Charlie’s wife, Muriel, is the complete opposite of her husband. She wants more and more money, and she’s not impressed by Charlie’s honest and kind nature. As Charlie and Muriel grow apart, Charlie and Yvonne grow together.

It Could Happen to You is one of my favorite movies about winning money. It’s a feel-good movie with lots of little twists and turns. It will make you laugh. And it might even may you cry.

But most of all, it will make you want to go out and buy a lottery ticket
even though you know the odds are stacked against you.

2. Walking Ned Devine

In Walking Ned Devine, when word reaches two elderly best friends that someone in their tiny Irish village has won the national lottery, they go to great lengths to find the winner so they can share the wealth. When they discover the “lucky” winner, Ned Devine, they find he has died of shock upon discovering his win.

Not wanting the money to go to waste, the village enters a pact to pretend Ned is still alive by having another man pose as him, and then to divide the money between them.

Casino Movies

3. National Lampoons Vegas Vacation

Vegas Vacation, a jokers-are-wild laugh fest including two other stars from past Vacations. Beverly D’Angelo is back as wife Ellen, doting on the guy she calls “Sparky,” and Randy Quaid again delights as grubby goof ball Cousin Eddie.

From Seigfried and Roy’s extravaganza to a Hoover Dam tour, from cruising to losing (Wallace Shawn as a shifty blackjack dealer) to amorous crooning (Wayne Newton falls for Ellen): watch Clark try to keep family and wallet together!

This is by far my favorite National Lampoon’s  (and possibly favorite casino) movie of all time. Vegas Vacation is funny on so many levels. I think the best part is, no matter how hard he studies different casino games, Clark loses money on every game he plays – especially blackjack.

While Rusty, his 17 year old son, manages to score a fake id and wins at everything he plays. Rusty ends up winning tons of cash, 3 new cars, and comped a luxury suite. While Clark obsessively blows the family nest egg trying to beat the casino and ends up turning to crazy cousin Eddy for a loan to try and get even.

4. “21”

This fictionalized account of the MIT blackjack team’s run in Las Vegas is a fun movie to watch. It has action, suspense, romance, and people winning lots of money. Even though the real story of the MIT blackjack team is not as glamorous, it’s always fun to watch people actually win money in Las Vegas.

In 21, Ben Campbell’s dream has always been to go to Harvard Medical School. In his senior year at M.I.T., he has been accepted to Harvard Medical School, but does not have the $300,000 it will take to finance it.

He impresses one of his professors, Mickey Rosa, in class with his quick mind and ability to deal with the issue at hand without letting his emotions take over.

Based on that, Mickey invites him into his small but secret society of students that have a system of winning at blackjack through counting cards. Hesitantly, he accepts their offer to be one of the big players on the understanding that he will do it only until he has enough to finance his Harvard education.

Once Ben gets a taste of the big life, it starts to affect his original plan, including having unforeseen consequences of alienating his closest friends. Ultimately, greed, pride, ego, desperation and revenge all play a role in how involvement in this group affects Ben’s life plan.


5. Oceans 13

In Ocean’s 13, when Reuben is double-crossed in a luxury hotel business with business partner Willie Bank, he has a heart attack. Danny Ocean and Rusty Ryan plot a heist with their friends to avenge Reuben by breaking Bank’s casino.

I’m a huge fan of the Oceans 11 movies. But Ocean’s 13 is the only one of them that involves people winning money. I’m sure you’ll love the scene where everyone at Bank’s new casino starts winning hundreds of thousands of dollars. But my favorite is the scene at the end with the Five Diamond Representative who gets tortured the entire movie finally gets redemption.

6. The Cooler

The Cooler is about the the unluckiest man in Vegas – a guy whose bad luck is contagious – is used by the last of the old time mob run casinos to kill high rollers’ action. That is, until he falls in love with a cocktail waitress and gets “lady luck,” which throws the situation into reverse. Things turn nasty when the casino director tries to break up the romance.

Poker Movies

7. Rounders

In Rounders, Mike McDermott (Damon) is a professional poker player and a law school student, in that order. One night, in an attempt to raise the capital for a trip to Las vegas to play in the World Series of Poker, McDermott loses his whole bankroll, $30K, to the owner of his favorite underground card club, Teddy KGB (John Malkovich).

The next day, he swears off cards, but we get the feeling he does so in order to keep his relationship with Jo (Gretchen Mol) alive. His resolve is shaken, and quickly destroyed, when his best friend growing up, Worm (Edward Norton), is released from prison, and McDermott soon finds himself back at the table.

Rounders might just go down in history as the greatest poker movie ever made. It was partially responsible for me starting to play the game seriously back in 2004. Many people have tried and failed to make movies and TV shows and live up to the legend of Rounders. Lucky for us, Miramax is working on a sequel to Rounders that is slated for 2014.

8. The Cincinnati Kid

In 1930s New Orleans, the Cincinnati Kid, a young stud poker player who travels from one big game to the next, stopping along the way up with various girls, is pitted against the legendary champion card-sharp Lancey Howard in a high-stakes poker game.

9. Maverick

Maverick is recreated from the character James Garner created in the 1950s TV program. Maverick is a gambler who would rather con someone than fight them. He needs an additional three thousand dollars in order to enter a winner-take-all poker game that begins in a few days.

He tries to win some money, tries to collect a few debts, and recover a little loot for the reward, all with a light-hearted air. He joins forces with a woman gambler with a marvelous, though fake, southern accent as the two both try and enter the game.

Pool/Billiards Movies

10. The Hustler

The Hustler is the story of “Fast” Eddie Felson. He is an expert pool player and spends his time along with partner Charlie Burns hustling a few dollars from unsuspecting dopes.

He decides that the time has come to play in the big leagues and challenges renowned pool player Minnesota Fats. In a forty-hour marathon, Felson hits both highs and lows: part way through the match he’s up $18,000 but doesn’t know when to quit.

He drinks too much and loses everything, including his confidence in his game. Slowly, he regroups and with the help of his girlfriend, Sarah Packard, builds up his self-esteem. Ignoring Sarah’s advice however, his driving ambition once again takes over leading to tragedy in his personal life and a re-match with Minnesota Fats.

11. The Color of Money

The Color of Money is the sequel to The Hustler. This time Eddie “Fast Eddy” Felson, a former pool player forced into retirement by gangsters, finds himself, self-respect, and finally, redemption when he enters a relationship with young pool player Tom Cruise very similar to his own early career.

As they travel together, Fast Eddy realizes how much he had lost, and can see the inevitable finale of their relationship as history begins to repeat itself. In an effort to avert tragedy, Eddy severs their relationship, and returns to his first love, pool. Finally, in a big Atlantic City tournament, Cruise returns the favor, and teaches Eddy the final lesson that allows him to finish his quest of re-discovery.

Betting Movies

12. Two for the Money

In Two for the Money, The story is related by Brandon Long (Matthew McConaughey) who begins life as a sports hero and just at the moment when he is ready to break in to the Pro Football domain, he fractures his leg in a winning touchdown.

Six years later, and still dreaming of making it as a player of football, finds him in the numbers game with a talent for picking winning teams and calling 900 numbers to urge gullible people to place bets according to his predictions. Enter Walter Abrams (Al Pacino), a recovering Gambler who is making it big in the sports gambling arena.

He coerces Brandon to join him in New York, wines him, dines him with the aid of his smart and beautiful wife Toni (Rene Russo), and in no time Brandon Long takes on the persona of John Anthony and makes it big as a TV personality who successfully bilks willing gambling people out of their money.

13. Let it Ride

Let it Ride follows an average kind of guy who has a slight problem with gambling goes to the track, and mystically, it seems as though he can’t lose, no matter how he bets; and he has an incredible day.


Game Show Movies

14. Slumdog Millionaire

Slumdog Millionaire tells the story of Jamal Malik, an 18 year-old orphan from the slums of Mumbai, who is about to experience the biggest day of his life. With the whole nation watching, he is just one question away from winning a staggering 20 million rupees on India’s “Kaun Banega Crorepati?”  (their version of Who Wants To Be A Millionaire?)

But when the show breaks for the night, police arrest him on suspicion of cheating; how could a street kid know so much? Desperate to prove his innocence, Jamal tells the story of his life in the slum where he and his brother grew up, of their adventures together on the road, of vicious encounters with local gangs, and of Latika, the girl he loved and lost.

Each chapter of his story reveals the key to the answer to one of the game show’s questions. Each chapter of Jamal’s increasingly layered story reveals where he learned the answers to the show’s seemingly impossible quizzes.

15. Quiz Show

Quiz Show is based on the true story of Charles Van Doren, the wildly popular champion of a successful TV show called “Twenty-One.” A national celebrity who appeared on the covers of both “Time” and “Life” magazines, Van Doren was an American folk hero.

In 1958, television quiz shows ruled the airwaves. Week after week audiences tuned in to watch as Van Doren, a popular English instructor at Columbia University and the product of one of America’s most renowned literary families, seemed to draw from his vast knowledge the correct answers to obscure questions.

Van Doren’s charming presence seduced 50 million people into believing him. But the truth is, viewers were fooled and saw only what the network and program’s producers wanted them to see. Then someone pulled the plug.

When disgruntled contestant Herbie Stempel charged that the quiz game was a fraud, Congressional investigator Richard Goodwin uncovered the facts that exposed the deception, and sent shock waves reverberating across America.

What do you think about this list? Are there any other must-see movies about winning money that I missed?

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