Movies Like The Lady is a Square

If you liked The Lady is a Square (1959), a romance and comedy movie directed by Herbert Wilcox, 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
Hollywood Stargirl (2022)
★ 6.6/10Also comedy and romance
When Stargirl's mother is hired as the costume designer on a movie, they relocate to L.A., where Stargirl quickly becomes involved with an eclectic assortment of characters.
2
Music and Lyrics (2007)
★ 6.5/10Also comedy and music
A washed-up '80s pop star gets a chance at a comeback when reigning pop diva Cora Corman invites him to write & record a duet with her, but there's a problem--Alex hasn't written a song in years; he's never written…
3
The Merry Widow (1934)
★ 6.8/10Also comedy and music
A prince from a small kingdom courts a wealthy widow to keep her money in the country.
4
A Cinderella Story: Starstruck (2021)
★ 6.8/10Also romance and comedy
Finley Tremaine, a small-town farm girl, longs to spread her wings and soar as an aspiring performer. When a Hollywood film crew arrives in her sleepy town, she is determined to land a role in the production and…
5
Find Me Falling (2024)
★ 6.6/10Also romance and comedy
After a failed comeback album, a rock star retreats to a cliffside home on Cyprus, only to find his new life complicated by visitors — and an old flame.
6
Marry Me (2022)
★ 6.6/10Also romance and comedy
After finding out about her fiancé's cheating ways, a pop superstar impulsively marries a total stranger. They must soon decide if two people from such different worlds can find true love.
7
How to Marry a Millionaire (1953)
★ 6.8/10Also comedy and romance
Three women set out to find eligible millionaires to marry, but find true love in the process.
8
The Fighting Temptations (2003)
★ 5.8/10Also comedy and music
Darrin Hill, a slick-talking but down-on- his-luck NYC advertising exec, returns to his hometown in Georgia to claim the inheritance his aunt left him. But before Darrin can collect the money, he must fulfill his…
9
Starstruck (2010)
★ 7.1/10Also romance and comedy
Pop star Christopher Wilde has fame, fortune and a big-budget Hollywood movie awaiting him. But after meeting Jessica Olson, a down-to-earth girl from the Midwest, he is faced with following his heart or doing what's…
10
Arlo the Alligator Boy (2021)
★ 6.8/10Also comedy and music
Upon learning that he is from New York City, a wide-eyed boy, who is half human and half alligator, decides to leave his sheltered life in the swamp and search for his long lost father. A musical adventure.
11
Cover Girl (1944)
★ 6.4/10Also music and comedy
A nightclub dancer makes it big in modeling, leaving her dancer boyfriend behind.
12
Pal Joey (1957)
★ 6.3/10Also music and romance
An opportunistic singer woos a wealthy widow to boost his career.
13
Falling for Figaro (2021)
★ 6.5/10Also romance and comedy
A brilliant young fund manager leaves her unfulfilling job and long-term boyfriend to chase her lifelong dream of becoming an opera singer in the Scottish Highlands.
14
Dames (1934)
★ 6.5/10Also romance and music
A reformer's daughter wins the lead role in a scandalous Broadway show.
15
A Very Jonas Christmas Movie (2025)
★ 6.2/10Also comedy and music
Kevin, Nick, and Joe Jonas face a series of escalating obstacles as they struggle to make it from London to New York in time to spend Christmas with their families.
16
Victor/Victoria (1982)
★ 7.3/10Also music and comedy
A struggling female soprano finds work playing a male female impersonator, but it complicates her personal life.
17
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.
18
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romance
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
19
French Girl (2024)
★ 6.2/10Also romance and comedy
Sweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an…
20
Love, Weddings & Other Disasters (2020)
★ 6/10Also romance and comedy
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.