Returning to the shared director's chair with Kelly, Donen and Kelly made their most renowned film, the classic Singin' in the Rain (1952). Filled with memorable musical and comic moments, including Jean Hagen's inability to act into the mike, Donald O'Connor's slapstick dance "Make 'Em Laugh," Cyd Charisse's sultry Broadway Ballet cameo and (of course) Kelly's solo precipitation revel, Singin' in the Rain's humorous ode to Hollywood's Golden Age showcased Donen and Kelly's visual inventiveness and buoyant touch, becoming the rare reflexive film that worked. Suffering a creative lag with a cluster of non-Freed musicals in 1952 and 1953, Donen's films nonetheless featured such notable dance moments as the onscreen pairing of top choreographer/dancers Gower Champion and Bob Fosse in Give a Girl a Break (1953). Back on track by 1954, Donen scored another success with the rousing Seven Brides for Seven Brothers (1954), showcasing Michael Kidd's choreography in CinemaScope. Joining forces with Kelly and the Freed unit one last time, Donen and company crafted the sardonic It's Always Fair Weather (1955). A sequel of sorts to On the Town, It's Always Fair Weather cast a critical eye on the musical's optimism and the encroaching phenomenon of television, and underlined Donen's talent for handling CinemaScope in Kelly, Kidd and Dan Dailey's energetic trash can dance. A flop, It's Always Fair Weather marked the end of Donen's tenure at MGM. A free agent, Donen confirmed that he was still one of the top directors of the musical with The Pajama Game and Funny Face in 1957.

A collaboration with co-director George Abbott and choreographer Fosse, The Pajama Game successfully transferred the show's Broadway luster to the screen, with the location-shot "Once a Year Day" taking full advantage of the medium's capability for staging expansive dance spectacles. Working again with Astaire, Donen made Funny Face a gloriously colorful, chic vehicle for the debonair dancer and his co-star Audrey Hepburn; Kay Thompson's "Think Pink" number threatens to steal the movie. Donen then re-teamed with Abbott and Fosse on another bright Broadway transplant, Damn Yankees (1958), featuring a rare screen turn by Gwen Verdon as the diabolically seductive Lola. Before the musical swooned in the 1960s, Donen shifted his attention to light comedy in the late '50s, including the smooth Cary Grant vehicles Indiscreet (1958) and The Grass is Greener (1961).

Working less often and mostly in Europe as the 1960s went on, Donen expanded his creative horizons beyond his 1950s studio films. Donen blended comedy, romance, and suspense in the Cary Grant/Audrey Hepburn starrer Charade (1963), a successful neo-Alfred Hitchcock mystery. Trying his hand at New Wave techniques, Donen notched a hit with nonlinear marital comedy Two for the Road (1967), assisted by stars Audrey Hepburn and Albert Finney's onscreen chemistry. Donen, Dudley Moore and Peter Cook's blasphemous [\comedy} Bedazzled (1968) became a cult favorite; Staircase (1969) was only notable for centering on a gay relationship between Richard Burton and Rex Harrison.

His brand of stylish classicism increasingly out of synch with the New Hollywood, despite Two for the Road's success, Donen made movies sporadically during the 1970s and early '80s. The subpar screen musical of Antoine de St. Exupery's The Little Prince in 1974 was momentarily enlivened by Fosse's cameo as the Snake. The clever 1930s send-up Movie Movie (1978), featuring a boxing drama and Busby Berkeley-esque musical, was a far better use of Donen's talents.

He attempted science fiction with the ill-conceived Saturn 3 (1980) and after the leering comedy Blame It on Rio (1984), Donen left movies, resurfacing occasionally in documentaries and to direct the TV version of A.R. Gurney's Love Letters (1999). Donen married several times, including to actress Yvette Mimieux.