Sondheim became a protege of Hammerstein's after befriending the lyricist's son in school, but he got his first big break when he was hired to adapt Shakespeare's Romeo and Juliet for Leonard Bernstein's West Side Story (1957). That show turned out to be one of the biggest hits and most memorable works of its time, and it brought many proposals for text-writing Sondheim's way --though he had always wanted to write music as well. Nevertheless, he worked with Jule Styne on Gypsy (1959), another enormous hit, and would later agree to collaborate with Richard Rodgers on the unsuccessful Do I Hear a Waltz? (1965).
Before that, however, Sondheim scored his first success as both composer and lyricist with A Funny Thing Happened on the Way to the Forum (1962). It was his last hit until Company (1970), a show about contemporary life and mores that did much to revolutionize the Broadway musical and, as many of Hammerstein's 50 shows had, move it more toward serious and exotic subjects. Since that time, Sondheim's shows have been amazingly daring in terms of subject matter, with unusual musical ideas and stunningly original lyrics. But they have not always been big hits, and have marked a time in theater when Broadway show music became a marginalized art form in terms of popular culture.
Nevertheless, Sondheim's shows of the 1970s and 1980s are benchmarks of the genre: Follies (1971) brought together aging Follies girls for a look at American middle age; A Little Night Music (1973) is based on Ingmar Bergman's film Smiles of a Summer Night and contains Sondheim's sole hit song, "Send in the Clowns"; Pacific Overtures (1976) ambitiously took on the subject of Japanese-American relations; Sweeney Todd (1979) was an operetta based on the British grand guignol tale of a murderous barber; Sunday in the Park with George (1984) was a biography of impressionist painter Georges Seurat; and Into the Woods (1987) wove together children's fairy tales with the theories of psychologist Bruno Bettelheim. At this writing, Sondheim's latest show is Assassins (1991), a short piece about presidential killers. In recent years, he has turned more to films, writing songs for Madonna in Dick Tracy in 1990 and reportedly working on an original movie musical.