Stanley Donen got his showbiz start early, working on Broadway beginning at age 16 in 1940. He soon became a choreographer as well, and an assistant to Gene Kelly, who was also getting his start. This connection would serve young Stanley well in the years to come, as he followed his pal to Hollywood, serving as choreographer and eventually co-director on a series films, beginning with On the Town (starring Kelly and Frank Sinatra) in 1949 and culminating with Singin' in the Rain in 1952. His relationship with Kelly eventually broke down for both professional and personal reasons (among other things, they were both in love with the same woman, who married Donen first, and then divorced him and eventually married Kelly), and Donen struck out on his own with films such as Funny Face (1957), starring Audrey Hepburn and Donen's childhood idol Fred Astaire.
Donen's career initially survived the decline of the movie musical, making a series of stylish, successful films in the 1960s such as Charade (1963, with Hepburn and Cary Grant), Arabesque (1966, with Gregory Peck and Sophia Loren; very underrated, in my opinion), and Two For the Road (1967, with Hepburn again, and Albert Finney). However, things tapered off rapidly in the 1970s, and after the poorly received Blame It On Rio in 1984, he never directed another film, though sporadic efforts on stage and TV would follow until the early 2000s. Donen received an Honorary Academy Award in 1997. He was perhaps the last surviving major director of Hollywood's golden age.
New York, New York
Singin' in the Rain