Donen's first film as director was 'On the Town' in 1949, again featuring Sinatra and Kelly, the latter sharing the director's credit with Donen. Together, the two brought a new style of dancing to the screen, less polished and sophisticated then that of Fred Astaire, but more virile and down to earth. 'On the Town' also made striking use of exterior locations in New York City. After directing Astaire in 'Royal Wedding' in 1951, Donen again took co-director's credit with Kelly on 'Singin' in the Rain' in 1952. Regarded as one of the indisputable masterpieces of the musical, it featured some extraordinary dancing from Kelly, Donald O'Connor, and Debbie Reynolds, not to mention a stunning cameo by Cyd Charisse.
'Seven Brides for Seven Brothers' in 1954 was an energetic musical of the backwoods, with choreography by Michael Kidd. Donen returned to working with Kelly and Kidd on 'It's Always Fair Weather' in 1955, in which Kidd played one of the leading roles in a a bitter sweet story of three soldiers reuniting ten years after the war. The more conventional 'Funny Face' in 1957 saw Donen once more working with Astaire. On 'The Pajama Game' in 1957 Donen shared director's credit with George Abbott, who wrote and directed the original theatrical performance of the work.
After a couple of romantic comedies with Cary Grant, 'Kiss Them for Me' in 1957 and 'Indiscreet' in 1958, Donen was reunited with Abbott on 'Damn Yankees!' in 1958, a musical set in the world of baseball. Abandoning the musical for comedy and romance, he worked twice more with Grant, on 'The Grass is Greener' in 1960 and 'Charade' in 1963. 'Two for the Road' in 1967 was a creditable effort at combining the road movie with romance. But Donen's later films are derivative, lacking the verve and freshness of his earlier work.