Movies Like A Sailor on Horseback

If you liked A Sailor on Horseback (1940), a comedy and romance movie directed by Emil A. Lingheim, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Heartbreakers (2001)
★ 6.2/10Also comedy and romance
Max and Page are a brilliant mother/daughter con team who have their grift down to a fine science. Max targets wealthy, willing men and marries them. Page then seduces them, and Max catches her husband in the act. Then…
2
Let's Make Love (1960)
★ 6.4/10Also comedy and romance
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
3
Love Is in the Air (2023)
★ 6.2/10Also romance and comedy
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
4
Champagne Problems (2025)
★ 6/10Also romance and comedy
A driven American exec heads to Paris determined to acquire a champagne brand by Christmas — and accidentally falls for the heir to the bubbly empire.
5
What a Way to Go! (1964)
★ 7.1/10Also comedy and romance
A four-time widow discusses her four marriages, in which all of her husbands became incredibly rich and died prematurely because of their drive to be rich.
6
I Love You Again (1940)
★ 7.2/10Also comedy and romance
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
7
Boot Camp (2024)
★ 6.1/10Also romance and comedy
Unathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self and ignore the others' expectations.
8
Players (2024)
★ 6.1/10Also romance and comedy
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
9
A Nice Girl Like You (2020)
★ 5.8/10Also comedy and romance
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…
10
Little Italy (2018)
★ 6.6/10Also comedy and romance
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
11
Falling for Christmas (2022)
★ 6.2/10Also romance and comedy
An engaged, spoiled hotel heiress finds herself in the care of a handsome, blue-collar lodge owner and his precocious daughter after getting amnesia in a skiing accident.
12
Mr. Lucky (1943)
★ 7.2/10Also comedy and romance
A conman poses as a war relief fundraiser, but when he falls for a charity worker, his conscience begins to trouble him.
13
Accident Man (2018)
★ 6.3/10Also comedy
Mike Fallon, the Accident Man, is a stone cold killer. When a loved one is murdered by his own crew, Fallon is forced to avenge the one person who actually meant something to him.
14
Watching the Detectives (2007)
★ 6.3/10Also comedy and romance
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…
15
Girl on a Bicycle (2013)
★ 5.9/10Also comedy and romance
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day…
16
Christmas with You (2022)
★ 5.8/10Also romance and comedy
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
17
Relationship Goals (2026)
★ 6.4/10Also romance and comedy
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her…
18
Maintenance Required (2025)
★ 6.1/10Also romance and comedy
Charlie, the fiercely independent owner of an all-female mechanic shop, is forced to reevaluate her future when a flashy corporate competitor moves in across the street. Seeking comfort, she turns to an anonymous…
19
Good Advice (2001)
★ 5.9/10Also comedy and romance
An investment banker loses everything and must discover what's really important in life.
20
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.