Movies like The Winning Five (1927)
The best movies like The Winning Five (1927) are A Woman (1915), Dough and Dynamite (1914) and Seriously Single (2020). If The Winning Five hooked you with its comedy, these 30 similar films are what to watch next, and every pick says why it matches.
The Winning Five
Quick picks
- Highest ratedJohn Mulaney: Kid Gorgeous at Radio City (2018)7.9/10 from 259 votes
- NewestSpa Weekend (2026)Released 2026
A Woman (1915)
Mother, father and daughter go to the park. The women doze off on a bench while the father plays a hide-and-seek game with a girl, blindfolded. Charlie leads him into a lake. Both dozing ladies on the bench fall for Charlie and invite him for dinner. The father returns home with a friend. Charlie rushes upstairs and dresses like a woman, shaving his mustache. Both men fall for Charlie.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDough and Dynamite (1914)
Pierre and Jacques are working as waiters at a restaurant where the cooks go on strike. When the two are forced to work as bakers, the striking cooks put dynamite in the dough, with explosive results.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSeriously Single (2020)
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThunderstruck (2012)
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLife of the Party (2018)
When her husband suddenly dumps her, longtime dedicated housewife Deanna turns regret into re-set by going back to college... landing in the same class and school as her daughter, who's not entirely sold on the idea. Plunging headlong into the campus experience, the increasingly outspoken Deanna – now Dee Rock – embraces freedom, fun, and frat boys on her own terms, finding her true self in a senior year no one ever expected.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisBeau Hunks (1931)
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Wedding Year (2019)
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisShanghaied (1915)
A shipowner intends to scuttle his ship on its last voyage to get the insurance money. Charlie, a tramp in love with the owner's daughter, is grabbed by the captain and promises to help him shanghai some seamen. The daughter stows away to follow Charlie. Charlie assists in the galley and attempts to serve food during a gale.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Chaplin Revue (1959)
Three Chaplin silent comedies "A Dog's Life", "Shoulder Arms", and "The Pilgrim" are strung together to form a single feature length film. Chaplin provides new music, narration, and a small amount of new connecting material. "Shoulder Arms" is now described as taking place in a time before "the atom bomb".
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisSpa Weekend (2026)
Four lifelong friends escape to a luxury spa retreat to reconnect, unwind and rediscover themselves, but their weekend of relaxation soon turns into a series of wild adventures and bad decisions.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMy Wife's Relations (1922)
Buster and a woman are mistakenly married and her initially unfriendly family begins to treat him nicely when they come to believe he has a large inheritance awaiting him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisJohn Mulaney: Kid Gorgeous at Radio City (2018)
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
Why it matches: Recommended by TMDB viewers · both comedy
Absolute CinemaMovies like thisMuch Ado About Nothing (2013)
A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisFrom Soup to Nuts (1928)
Inexperienced waiters (Laurel & Hardy) are hired for a swank dinner party.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Fixer Uppers (1935)
Stan and Ollie are greeting card salesmen who agree to help a woman put a spark in her loveless marriage by making her husband jealous.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisLittle Big League (1994)
When the owner of the Minnesota Twins passes away, he bequeaths the team to his preteen grandson. The newly minted head honcho quickly appoints himself manager, causing unrest in an organization that struggles to take orders from a 12-year-old.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisMe Time (2022)
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisThe Trouble with Angels (1966)
Mary and her friend, Rachel, are new students at St. Francis Academy, a boarding school run by the iron fist of Mother Superior. The immature teens grow bored and begin playing pranks on both the unsuspecting nuns and their unpleasant classmates, becoming a constant thorn in Mother Superior's side. However, as the years pass, Mary and Rachel slowly mature and begin to see the nuns in a different light.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSextuplets (2019)
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Lady of Lyons, N.Y. (1926)
Bill Grimm, a taxicab driver, falls in love with Barbara Baxter, from Lyons, New York, the minute she steps off the train, and has him take her to Mrs. Whipple's boarding house, in spite of the interference by Jack Fairfax, Bill's rival. Boarders at Mrs. Whipple's include a prizefighter named "Butch,", his manager O'Brien, and Pansy the maid. This first entry in the series introduces the leading characters in the future films, and a few comical interludes.
Why it matches: Similar story and style · both comedy
Sweedie in Vaudeville (1915)
Sweedie, the theater's scrubwoman, in love with the unappreciative props, become enamored with the idea of a stage career.
Why it matches: Similar story and style · both comedy
Dear Old Calford (1928)
Episode #7 in the third series of the Universal Pictures serial "The Collegians".
Why it matches: Similar story and style · both comedy
Calford on Horseback (1928)
Episode #8 in the third series of the Universal Pictures serial "The Collegians".
Why it matches: Similar story and style · both comedy
The Bookworm Hero (1928)
Episode #9 in the third series of the Universal Pictures serial "The Collegians".
Why it matches: Similar story and style · both comedy
The Winning Goal (1928)
Episode #9 of the second series of the Universal Pictures serial "The Collegians".
Why it matches: Similar story and style · both comedy
Calford vs. Redskins (1928)
Episode #2 of the third series in the Universal Pictures serial "The Collegians".
Why it matches: Similar story and style · both comedy
Kicking Through (1928)
Episode #3 of the third series of the Universal Pictures serial "The Collegians".
Why it matches: Similar story and style · both comedy
Fighting Spirit (1927)
Episode 6 of The Collegians silent film series (consisting of 46 chapters) full of high jinks and romance!
Why it matches: Similar story and style · both comedy
Breaking Records (1927)
Chapter 11 of the silent serial "The Collegians".
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like The Winning Five?
The closest matches to The Winning Five are A Woman (1915), Dough and Dynamite (1914) and Seriously Single (2020). Below are 27 more, each with the reason it matches.
What should I watch after The Winning Five?
Start with A Woman (1915), the closest match to The Winning Five.
What is the highest-rated movie like The Winning Five?
John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.
What is the newest movie like The Winning Five?
Spa Weekend (2026) is the most recent release on this list.
Are there English movies like The Winning Five?
Yes: A Woman (1915), Dough and Dynamite (1914) and Seriously Single (2020).
How are movies similar to The Winning Five chosen?
First come films that Trakt’s viewers watch alongside The Winning Five, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.