Movies like Born to Gamble (1987)
The best movies like Born to Gamble (1987) are You Will Meet a Tall Dark Stranger (2010), The Baltimorons (2025) and He Said, She Said (1991). If Born to Gamble hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Odd Couple (1968)7.4/10 from 691 votes
- NewestIs This Thing On? (2025)Released 2025
You Will Meet a Tall Dark Stranger (2010)
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisThe Baltimorons (2025)
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHe Said, She Said (1991)
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisA California Christmas (2020)
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisChéri (2009)
The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisPeace, Love & Misunderstanding (2011)
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisA California Christmas: City Lights (2021)
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisIs This Thing On? (2025)
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to navigate co-parenting, identity, and whether love can take a new form.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisOther People's Money (1991)
When a corporate raider threatens a hostile takeover of a 'mom and pop' company, the patriarch of the company enlists the help of his wife's attractive daughter—who is a lawyer—to stop the takeover. However, the raider soon becomes infatuated with her, and enjoys the legal manoeuvring as he tries to win her heart.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisI Met a Girl (2020)
An aspiring musician struggling with schizophrenia falls for a mysterious woman who may be all in his head. When she suddenly vanishes, he takes off on a cross-country journey across Australia to find her, forcing his long-suffering brother to chase after him.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisL.A. Without a Map (1999)
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.
Why it matches: Recommended by TMDB viewers · both drama & comedy
SnoozefestMovies like thisWhich Brings Me to You (2023)
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove Accidentally (2022)
Alexa and Jason are competing for a position at an advertising firm when their partners break up with them. Alexa mistakenly texts Jason, and they start a phone-only relationship. When they meet and the truth comes out, will true love prevail?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPaper Heart (2009)
Paper Heart follows Nick and Charlyne on a cross-country journey to document what exactly "love" is. Interviewing ministers, happily married couples, chemists, romance novelists, divorce lawyers, a group of children and more, the determined young girl attempts to find definition and perhaps even experience the mysterious emotion.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisFools Rush In (1997)
After a one night stand with Alex, Isabel realizes that she is pregnant and they decide to get married. However, along with the marriage comes compromise of one's own cultural traditions.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJersey Girl (2004)
Ollie Trinke is a young, suave music publicist who seems to have it all, with a new wife and a baby on the way. But life deals him a bum hand when he's suddenly faced with single fatherhood, a defunct career and having to move in with his father. To bounce back, it takes a new love and the courage instilled in him by his daughter.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDanny Deckchair (2003)
An unappreciated laborer's patience reaches breaking point when his girlfriend cancels a romantic holiday. Making light of the situation, he decides to tie hundreds of helium balloons to a chair in an outlandish bid to float to a new life.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe God of Cookery (1996)
The most renowned and feared chef in the world loses his title of God of Cookery because of his pompous attitude. Humbled, he sets out to reclaim his title.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisBlind (2017)
A novelist is blinded in a car crash that killed his wife and several years later rediscovers his passion for life and writing when he embarks on an affair with the neglected wife of an indicted businessman.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisThe Right Kind of Wrong (2013)
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisThe Tale of Three Girls (1968)
Three women each have their own ambitions and aspirations. The first dreams of fame and fortune and meets a rich, married man she attempts to court. The second is a secretary with designs on her boss, even though he too is married. Having learned from her friends' experiences, the third takes an altogether different path.
Why it matches: Similar story and style · both comedy & romance
Stranded in Paradise (2014)
When a driven HR exec loses her high-powered job, she travels to Puerto Rico in an attempt to save her career at a business conference. But as the trip quickly becomes a disaster and a hurricane shuts down the whole island, she meets a handsome world traveler who gives her a new perspective on finding passion in life and love.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisDonga Mogudu (1987)
Donga Mogudu is a action comedy based movie in which, Chiranjiveei played dual role in this movie. Ravi Teja (Chiranjeevi) is an industrialist, who owns a textile company. He is a successful person in business but his personal life lacks harmony and peace. Tortured by his wife Madhavi and her mother, he finds life miserable. Meanwhile, his opponents cannot digest his success in business and plan to stop him from getting yet another business deal. Here, he meets Nagaraju (Chiranjeevi), who is a small-time thief. Ravi Teja is saved by Nagaraju and he plans to exchange their positions, so that his problems can be solved forever. Nagaraju agrees, and teaches madhavi, her mother, and Ravi Teja
Why it matches: Similar story and style · both comedy & drama
Blazing Saddles (1974)
Crafty railroad worker Bart becomes the first Black sheriff of Rock Ridge, a frontier town about to be destroyed in order to make way for a new railroad. Initially, the citizens of Rock Ridge harbor a racial bias toward their new protector. However, they warm to him after realizing that Bart and his perpetually drunk gunfighter friend Jim are their only defense against a wave of thugs sent to rid the town of its population.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisThe Odd Couple (1968)
In New York, Felix, a neurotic news writer who just broke up with his wife, is urged by his chaotic friend Oscar, a sports journalist, to move in with him, but their lifestyles are as different as night and day are, so Felix's ideas about housekeeping soon begin to irritate Oscar.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisIt's a Mad, Mad, Mad, Mad World (1963)
A group of strangers come across a man dying after a car crash who proceeds to tell them about the $350,000 he buried in California. What follows is the madcap adventures of those strangers as each attempts to claim the prize for himself.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisEspèces menacées (2001)
An accountant, presumed honest, inadvertently finds 7 million francs in his bag and decides to change his life.
Why it matches: Similar story and style · both comedy
Octopus (2015)
Squid have 10 legs. Octopuses have 8 legs. Added together, that’s 18 legs.
Why it matches: Similar story and style · both comedy
Nad wielką wodą (1962)
A brief history of the malice of inanimate objects.
Why it matches: Similar story and style · both comedy
From Kuleshov to Berlanga (2004)
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Born to Gamble?
The closest matches to Born to Gamble are You Will Meet a Tall Dark Stranger (2010), The Baltimorons (2025) and He Said, She Said (1991). Below are 27 more, each with the reason it matches.
What should I watch after Born to Gamble?
Start with You Will Meet a Tall Dark Stranger (2010), the closest match to Born to Gamble.
What is the highest-rated movie like Born to Gamble?
The Odd Couple (1968), rated 7.4/10 by 691 TMDB users.
What is the newest movie like Born to Gamble?
Is This Thing On? (2025) is the most recent release on this list.
How are movies similar to Born to Gamble chosen?
First come films that Trakt’s viewers watch alongside Born to Gamble, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.