Movies like It's Fun to Gamble, If You Win
The best movies like It's Fun to Gamble, If You Win are Easy Money (1983), Let It Ride (1989) and Vegas Vacation (1997). If It's Fun to Gamble, If You Win hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedDirty Rotten Scoundrels (1988)7.1/10 from 1,110 votes
- NewestQuiz Lady (2023)Released 2023
Easy Money (1983)
To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLet It Ride (1989)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisVegas Vacation (1997)
The Griswold family hits the road again for a typically ill-fated vacation, this time to the glitzy mecca of slots and showgirls—Las Vegas.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDirty Work (1998)
Unemployed and recently dumped, Mitch and his buddy Sam start a revenge-for-hire business to raise the $50,000 that Sam's father needs to get a heart transplant.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisA Bad Moms Christmas (2017)
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families wasn’t hard enough, they have to do all of that while hosting and entertaining their own mothers.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisAnalyze That (2002)
The mafia's Paul Vitti is back in prison and will need some serious counseling when he gets out. Naturally, he returns to his analyst Dr. Ben Sobel for help and finds that Sobel needs some serious help himself as he has inherited the family practice, as well as an excess stock of stress.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisRoom Service (1938)
Broke Gordon Miller tries to land a backer for his new play while he has to deal with with the hotel manager trying to evict him and his cast.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGet Shorty (1995)
Chili Palmer is a Miami mobster who gets sent to L.A. to collect a bad debt from Harry Zimm, a Hollywood producer who specializes in cheesy horror films. When Chili meets Harry's leading lady, the romantic sparks fly. After pitching his own life story as a movie idea, Chili learns that being a mobster and being a Hollywood producer really aren't all that different.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohnny Dangerously (1984)
An honest, goodhearted man is forced to turn to a life of crime to finance his neurotic mother's skyrocketing medical bills.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisQuiz Lady (2023)
A brilliant but tightly wound, gameshow-obsessed young woman, Anne, and her estranged, train-wreck of a sister, Jenny, must work together to help cover their mother's gambling debts. When Anne's beloved dog is kidnapped, they set out on a wild, cross-country trek to get the cash the only way they know how: by turning Anne into a bona-fide gameshow champion.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisCa$h (2010)
A stroke of good luck turns lethal for Sam Phelan and his wife Leslie when they are faced with a life-changing decision that brings strange and sinister Pyke Kubic to their doorstep. As Pyke leads Sam and Leslie on a tumultuous adventure through the streets of Chicago, each are pulled deeper and deeper into a desperate spiral of deception and violence – all in the name of money.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like this29th Street (1991)
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSgt. Bilko (1996)
The US army is known for churning out lean mean fighting machines intent on protecting our great nation. Sergeant Ernie Bilko is the leader of a ragtag group of the sorriest soldiers ever to enlist in the armed forces.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisDirty Rotten Scoundrels (1988)
Con artist Lawrence Jamieson is a longtime resident of a luxurious coastal resort, where he enjoys the lavish fruits of his deceptions -- that is, until a competitor, Freddy Benson, shows up. When the new guy's lowbrow tactics impinge on his own sophisticated work and believing him to be the infamous conman 'The Jackal', Lawrence resolves to get rid of him. Confident of his own duplicitous talents, he challenges Freddy to a winner-takes-all competition: whoever swindles their latest mark, American heiress Janet Colgate, out of $50,000 first can stay, while the other must leave town.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisTrailer Park Boys: Don't Legalize It (2014)
Out of jail and broke, Julian concocts an outrageously greasy scheme to get rich and, to make it even greasier, he will have to deliver his product to his arch-enemy, Cyrus, who’s waiting in Montreal to close the dirty deal. Meanwhile, Ricky’s dope growing business is under a major threat when the government announces a plan to legalize marijuana. Bubbles reluctantly joins them on his own quest to claim an inheritance left to him by his long-lost parents.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Air Up There (1994)
Jimmy Dolan is a college basketball coach who wants a big promotion. To get it, he needs to make a dramatic find. He ends up deep in Africa, hoping to recruit Saleh, a huge basketball prodigy Jimmy glimpsed in a home movie. But Saleh is the chief's son and has responsibilities at home, since the tribe's land is threatened by a mining company with its own hotshot basketball team.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGrandma's Boy (2006)
Even though he's 35, Alex acts more like he's 13, spending his days as the world's oldest video game tester and his evenings developing the next big Xbox game. But when he gets kicked out of his apartment, he's forced to move in with his grandmother.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHis Kind of Woman (1951)
Career gambler Dan Milner agrees to a $50,000 deal to leave the USA for Mexico, only to find himself entangled with fellow guests at a luxurious resort and suspecting that the man who hired him may be the deported crime boss Nick Ferraro aiming to re-enter to the USA.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisNo Deposit, No Return (1976)
Two rich children devise a way to escape their grandfather and visit their mother. Unfortunately for two hapless safe crackers, they become part of the plan.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Hangover Part III (2013)
This time, there's no wedding. No bachelor party. What could go wrong, right? But when the Wolfpack hits the road, all bets are off.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBarbershop (2002)
A day in the life of a barbershop on the south side of Chicago. Calvin, who inherited the struggling business from his deceased father, views the shop as nothing but a burden and waste of his time. After selling the shop to a local loan shark, Calvin slowly begins to see his father's vision and legacy and struggles with the notion that he just sold it out.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisSt Trinian's (2007)
When their beloved school is threatened with closure should the powers that be fail to raise the proper funds, the girls scheme to steal a priceless painting and use the profits to pull St. Trinian's out of the red.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisOld Men in New Cars: In China They Eat Dogs II (2002)
The last wish of the dying "Monk" is for his foster child, Harald, to find his real son, Ludvig. But the latter is currently in a Swedish prison cell...
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisBuffalo '66 (1998)
Billy is released after five years in prison. In the next moment, he kidnaps teenage student Layla and visits his parents with her, pretending she is his girlfriend and they will soon marry.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisIntacto (2001)
An enigmatic tale of four people whose lives are intertwined by destiny are subject to the laws of fate. They discover that luck is something they cannot afford to be without as they gamble with the highest stakes possible in a deadly game from which only one of them will emerge intact.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisSüperseks (2004)
23-year-old Elviz from Hamburg-Altona is in a tight spot: his uncle wants the 50,000 euros he once lent Elviz back — he promises to seize Elviz's mother's property on the Turkish Riviera otherwise. But Elviz knows how to make money quickly these days and founds the first Turkish-language telephone sex hotline, "Süperseks". It's going great - and only gets Elviz into more trouble when his new girlfriend Anna applies for a job with "Süperseks", unaware of who is behind the company.
Why it matches: Similar story and style · both comedy
Lost in America (1985)
David and Linda Howard are successful yuppies from LA. When he gets a job disappointment, David convinces Linda that they should quit their jobs, liquidate their assets, and emulate the movie Easy Rider, spending the rest of their lives traveling around America...in a Winnebago.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisThe Collector (2004)
A romantic comedy set in the world of gambling, debt collecting and professional boxing. Laura is an unlucky gambler with a huge debt, she crosses paths with Claus, a former boxer who now makes a living as a debt collector. Laura is cheating, scamming, and lying and eventually life catches up with her. Claus is trying to regain his self respect and start anew. Together, they make an awkward but very charming couple on the verge of love. It is a story about trust, friendship, new beginnings, getting a second chance and doing the right thing.
Why it matches: Similar story and style · both comedy
The Sport of Kings (1931)
Algernon Sprigg, a horse-racing fanatic, is convinced that everyone is a gambler at heart. To prove his theory, he bets a friend that he can convert Amos Purdie, the puritanical head of an anti-betting association, into a punter within a week.
Why it matches: Similar story and style · both comedy
So You Want to Play the Horses (1946)
In this outing, Joe loves playing the horses and shows what you can do to improve your odds of winning.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like It's Fun to Gamble, If You Win?
The closest matches to It's Fun to Gamble, If You Win are Easy Money (1983), Let It Ride (1989) and Vegas Vacation (1997). Below are 27 more, each with the reason it matches.
What should I watch after It's Fun to Gamble, If You Win?
Start with Easy Money (1983), the closest match to It's Fun to Gamble, If You Win.
What is the highest-rated movie like It's Fun to Gamble, If You Win?
Dirty Rotten Scoundrels (1988), rated 7.1/10 by 1,110 TMDB users.
What is the newest movie like It's Fun to Gamble, If You Win?
Quiz Lady (2023) is the most recent release on this list.
How are movies similar to It's Fun to Gamble, If You Win chosen?
First come films that Trakt’s viewers watch alongside It's Fun to Gamble, If You Win, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.