Movies like Winners & Losers
The best movies like Winners & Losers are Two for the Money (2005), Pillow Talk (1959) and Good Neighbor Sam (1964). If Winners & Losers hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Winners & Losers
Quick picks
- Highest ratedTrading Places (1983)7.2/10 from 3,844 votes
- NewestSidelined: The QB and Me (2025)Released 2025
Two for the Money (2005)
A former college athlete joins forces with a sports consultant to handicap football games for high-rolling gamblers.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisPillow Talk (1959)
Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a complaint against him, Brad sets about to seduce her in the guise of a sincere and upstanding Texas rancher. When mutual friend Jonathan discovers that his best friend is moving in on the girl he desires, however, sparks fly.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisGood Neighbor Sam (1964)
To help his divorced neighbor claim a substantial inheritance, a family man poses as her husband. The ruse spills over into his career in advertising, and his recent promotion relies on his wholesome and moral appearance.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHardball (2001)
An aimless young man who is scalping tickets, gambling and drinking, agrees to coach a Little League team from the Cabrini Green housing project in Chicago as a condition of getting a loan from a friend.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDuplex (2003)
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisWalk on the Wild Side (1962)
At a 1930s New Orleans bordello, Hallie is the main attraction for both clients and the shrewd madam. The arrival of Dove Linkhorn, her lovesick sweetheart from three years ago, disrupts the normal and triggers a chain of events involving a number of people, including the young woman he travelled with, who is now the Doll House's newest employee.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHow to Lose a Guy in 10 Days (2003)
It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks!
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisTrading Places (1983)
A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisA Bride for Christmas (2012)
Bride-to-be Jessie Patterson calls off her third engagement - during the ceremony! She swears off serious relationships, until she meets and is pursued by Aiden MacTiernan. Aiden, on the other hand, has bet his friends he is marriage material, and can find a fiancé in the four weeks leading up to Christmas. When Jessie and Aiden begin to fall for each other, Jessie must decide if she is ready for serious love, and Aiden must decide if his bet is worth risking his relationship with Jessie.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Choice (2016)
Travis and Gabby first meet as neighbors in a small coastal town and wind up in a relationship that is tested by life's most defining events.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisFast Girls (2012)
A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSidelined: The QB and Me (2025)
Dallas, a burdened but headstrong dancer, is determined to get into the best dance school in the country—her late mother’s alma mater. However, that dream is suddenly derailed when the cheeky yet secretly grieving football star, Drayton, crashes into her life with a unique story of his own. Will the two of them be able to grow into their dreams together, or will their dreams be sidelined?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisWhat Maisie Knew (2013)
In New York City, six-year-old Maisie is caught in the middle of a bitter custody battle between her self-absorbed parents—an aging rock singer mother and a distracted art dealer father. As both quickly marry new partners to strengthen their legal standing, Maisie is shuttled back and forth in an endless game of emotional point-scoring. Yet amid the chaos and upheaval, Maisie begins to find true comfort and affection in her new step-parents.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisCalifornia Split (1974)
Carefree single guy Charlie Waters rooms with two lovely prostitutes, Barbara Miller and Susan Peters, and lives to gamble. Along with his glum betting buddy, Bill Denny, Charlie sets out on a gambling streak in search of the ever-elusive big payday. While Charlie and Bill have some lucky moments, they also have to contend with serious setbacks that threaten to derail their hedonistic betting binge.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisGoal! (2005)
Like millions of kids around the world, Santiago harbors the dream of being a professional footballer... However, living in the Barrios section of Los Angeles, he thinks it is only that—a dream. Until one day an extraordinary turn of events has him trying out for Premiership club Newcastle United.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Million Pound Note (1954)
An impoverished American sailor is fortunate enough to be passing the house of two rich gentlemen who have conceived the crazy idea of distributing a note worth one million pounds. The sailor finds that whenever he tries to use the note to buy something, people treat him like a king and let him have whatever he likes for free. Ultimately, the money proves to be more troublesome than it is worth when it almost costs him his dignity and the woman he loves.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisSide Street (1950)
A struggling young father-to-be gives in to temptation and impulsively steals an envelope of money from the office of a corrupt attorney. Instead of a few hundred dollars, it contains $30,000. When he decides to return the money, things go wrong - and that is only the beginning of his troubles.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSome Kind of Wonderful (1987)
Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and tries to convince him to stop pursuing Amanda. Matters are further complicated when Keith's invitation draws the ire of Amanda's rich yet snobby ex-boyfriend, Hardy Jenns, who makes plans to get even.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisTyler Perry's The Family That Preys (2008)
Wealthy socialite Charlotte Cartwright and her dear friend Alice Pratt, a working class woman of high ideals, have enjoyed a lasting friendship throughout several decades. Recently, their lives have become mired in turmoil as their adult children’s extramarital affairs, unethical business practices, and a dark secret threaten to derail family fortunes and unravel the lives of all involved. Charlotte and Alice decide to take a breather from it all by making a cross-country road trip in which they rediscover themselves and possibly find a way to save their families from ruin.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisWatching the Detectives (2007)
Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.
Why it matches: Recommended by TMDB viewers
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Frequently asked questions
What are the best movies like Winners & Losers?
The closest matches to Winners & Losers are Two for the Money (2005), Pillow Talk (1959) and Good Neighbor Sam (1964). Below are 17 more, each with the reason it matches.
What should I watch after Winners & Losers?
Start with Two for the Money (2005), the closest match to Winners & Losers.
What is the highest-rated movie like Winners & Losers?
Trading Places (1983), rated 7.2/10 by 3,844 TMDB users.
What is the newest movie like Winners & Losers?
Sidelined: The QB and Me (2025) is the most recent release on this list.
Are there English movies like Winners & Losers?
Yes: Two for the Money (2005), Pillow Talk (1959) and Good Neighbor Sam (1964).
How are movies similar to Winners & Losers chosen?
First come films that Trakt’s viewers watch alongside Winners & Losers, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.