Movies Like Carefree

If you liked Carefree (1938), a music and comedy movie directed by Mark Sandrich, 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
Anchors Aweigh (1945)
★ 6.8/10Also music and comedy
Two sailors on shore leave head out for four days of partying – only to become involved in the affairs of an aspiring singer and her precocious nephew.
2
High Society (1956)
★ 6.8/10Also music and comedy
With socialite Tracy Lord about to remarry, her ex-husband - with the help of a sympathetic reporter - has 48 hours to convince her that she really still loves him.
3
Funny Face (1957)
★ 7/10Also music and comedy
A shy Greenwich Village book clerk is discovered by a fashion photographer and whisked off to Paris where she becomes a reluctant model.
4
Another Cinderella Story (2008)
★ 7.3/10Also music and comedy
A guy who danced with what could be the girl of his dreams at a costume ball only has one hint at her identity: the Zune she left behind as she rushed home in order to make her curfew. And with a once-in-a-lifetime…
5
Top Hat (1935)
★ 7.2/10Also music and comedy
Showman Jerry Travers is working for producer Horace Hardwick in London. Jerry demonstrates his new dance steps late one night in Horace's hotel room, much to the annoyance of sleeping Dale Tremont below. She goes…
6
G.I. Blues (1960)
★ 6.5/10Also music and comedy
Stationed in West Germany, soldier Tulsa McLean hopes to open a nightclub once he's discharged. Although he may lack the capital for such a venture, a chance to raise the cash comes his way through a friendly wager…
7
Just My Luck (2006)
★ 6.2/10Also comedy and romance
Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.
8
The Tender Trap (1955)
★ 6.2/10Also music and comedy
A young actress flirts demurely with a swinging Manhattan bachelor who thinks he has it made.
9
Finding Emily (2026)
★ 6.9/10Also romance and comedy
When a lovesick musician is given the wrong number for his dream girl, he teams up with a driven psychology student to find her. Together, they spark a hilarious campus-wide frenzy that tests their own hearts and…
10
Kiss Me, Stupid (1964)
★ 7/10Also comedy and romance
While traveling home from Vegas, an amorous lounge singer named Dino gets conned by a local mechanic/songwriter into staying in town for the night. The mechanic's songwriting partner, Orville, offers Dino his home for…
11
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.
12
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.
13
An American in Paris (1951)
★ 7/10Also music and romance
Jerry Mulligan is an exuberant American expatriate in Paris trying to make a reputation as a painter. His friend Adam is a struggling concert pianist who's a long time associate of a famous French singer, Henri Baurel…
14
Speedway (1968)
★ 5.9/10Also comedy and music
A race car driver tries to outrun the beautiful tax auditor out to settle his account.
15
Meet Me Next Christmas (2024)
★ 6.3/10Also romance and comedy
On a quest to reconnect with the man of her dreams, Layla races across New York City to find a ticket to a sold-out Pentatonix Christmas Eve concert.
16
The Boy Friend (1971)
★ 6.4/10Also music and comedy
When the leading lady of a low-budget musical revue sprains her ankle, the assistant stage manager is forced to understudy and perform in her place.
17
Thoroughly Modern Millie (1967)
★ 6.9/10Also comedy and music
Millie Dillmount, a fearless young lady fresh from Salina, Kansas, determined to experience Life, sets out to see the world in the rip-roaring Twenties. With high spirits and wearing one of those new high hemlines, she…
18
Viva Las Vegas (1964)
★ 6.1/10Also music and romance
Lucky Jackson arrives in Las Vegas with his car literally in tow ready for the first Grand Prix — once he has the money for an engine. He gets the cash easily enough but mislays it when the pretty pool manageress takes…
19
The Truth About Cats & Dogs (1996)
★ 6.1/10Also comedy and romance
A successful veterinarian and radio show host with low self-esteem asks her model friend to impersonate her when a handsome man wants to see her.
20
Little Manhattan (2005)
★ 7.2/10Also comedy and romance
Ten-year-old Gabe Burton is just an average kid growing up in Manhattan until Rosemary Telesco walks into his karate class. But before Gabe can tell Rosemary how he feels, she reveals that she won't be going to public…