Most Similar Movies to Gypsy (1962)
If you are looking for movies like Gypsy (1962), you might like movies tagged with keyword : musical, drama, romance, female protagonist, show business, mother-daughter relationship, ambition, classic hollywood, 1960s, coming of age, emotional conflict, fame and fortune, melodrama, lavish costumes, nostalgia, stardom, family conflict, american film, color film, broadway adaptation .
Gypsy (1993), The Umbrellas of Cherbourg (1964), The Band Wagon (1953), There's No Business Like Show Business (1954), Swing High, Swing Low (1937), West Side Story (1961), The Harvey Girls (1946) ... Let's take a look at the following list...

Gypsy (1993)
Stage-mother Mama Rose (Bette Midler) sees one daughter quit, while her other one (Cynthia Gibb) becomes stripper Gypsy Rose Lee.
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The Umbrellas of Cherbourg (1964)
A young woman separated from her lover by war faces a life-altering decision.
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The Band Wagon (1953)
Two playwrights bring a movie dancer (Fred Astaire) to New York for a Broadway show with a ballerina (Cyd Charisse).
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There's No Business Like Show Business (1954)
Molly and Terry Donahue, plus their three children, are The Five Donahues. Son Tim meets hat-check girl Vicky and the family act begins to fall apart.
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Swing High, Swing Low (1937)
A hair-dresser stranded in Panama moves in with an ex-soldier and his hypochondriac roommate; she and the former fall in love, but their romance is threatened by success and the arrival of his old flame.
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West Side Story (1961)
Two youngsters from rival New York City gangs fall in love, but tensions between their respective friends build toward tragedy.
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The Harvey Girls (1946)
On a train trip West to become a mail-order bride, Susan Bradley (Judy Garland) meets a cheery crew of young women travelling out to open a "Harvey House" restaurant at a remote whistle-stop.
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I Could Go on Singing (1963)
Jenny Bowman is a successful singer who visits David Donne to see her son Matt again, spending a few glorious days with him while his father is away in Rome in an attempt to attain the family that she never had.
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Pal Joey (1957)
Joey Evans' a charming, handsome, funny, talented a-1st class, A-N°.1 - heel. When Joey meets the former chorus girl and now is the rich widow, Vera Simpson, the pair of lecherous souls seem made for each other.
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Daddy Long Legs (1955)
A wealthy American has a chance encounter with a joyful young French woman, and anonymously pays for her education. She writes letters to her mysterious benefactor, nicknaming him from the description given by some of her fellow orphans.
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Listen, Darling (1938)
Young Pinkie Wingate and her pal Buzz will do anything to stop Pinkie’s widowed mother from entering into a loveless marriage with the town’s fuddy-duddy banker – including kidnapping!
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The Jazz Singer (1927)
The son of a Jewish Cantor must defy the traditions of his religious father in order to pursue his dream of becoming a jazz singer.
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Dreamgirls (2006)
A trio of black female soul singers cross over to the pop charts in the early 1960s, facing their own personal struggles along the way.
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Till the Clouds Roll By (1946)
Biography of songwriter and Broadway pioneer, Jerome Kern (Robert Walker). Unable to find immediate success in the U.S., Kern sought recognition abroad. He journeyed to England where his dreams of success became real and where he met his future wife Eva Leale (Dorothy Patrick).
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Blue Skies (1946)
An ex-dancer and New York radio star narrates his love story for a band singer who loved a self-centered man who was unable to commit to his nightclub business or his family.
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Ladies of the Chorus (1949)
A chorus girl falls in love with a wealthy young man, but their relationship is jeopardized by her mother's fears about the reaction of his family.
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It's Always Fair Weather (1955)
A talk-show staffer (Cyd Charisse) puts a fight manager (Gene Kelly), adman (Dan Dailey) and cook on TV 10 years after they parted as GIs.
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