Kelly is best known for his performances in An American in Paris (1951), which won the Academy Award for Best Picture, Singin' in the Rain (1952), which he and Donen directed and choreographed, and other musical films of that era such as Cover Girl (1944) and Anchors Aweigh (1945), for which he was nominated for an Academy Award for Best Actor. On the Town (1949), which he co-directed with Donen, was his directorial debut. Later in the 1950s, as musicals waned in popularity, he starred in Brigadoon (1954) and It's Always Fair Weather (1955), the last film he directed with Donen. His solo directorial debut was Invitation to the Dance (1956), one of the last MGM musicals, which was not a commercial success.
Kelly made his film debut with Judy Garland in For Me and My Gal (1942), with whom he also appeared in The Pirate (1948) and Summer Stock (1950). He also appeared in the dramas Black Hand (1950) and Inherit the Wind (1960), for which he received critical praise.
He continued as a director in the 1960s, with his credits including A Guide for the Married Man (1967) and Hello, Dolly! (1969), which received an Oscar nomination for Best Picture. He co-hosted and appeared in Ziegfeld Follies (1946), That's Entertainment! (1974), That's Entertainment, Part II (1976), That's Dancing! (1985), and That's Entertainment, Part III (1994).

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