In 1961 he began a collaboration with songwriters Burt Bacharach and Hal David that resulted in the recording of his first hit single, "(I Wanna) Love My Life Away", followed by his first big hit, "Town Without Pity" that same year. This song would win the Golden Globe Award for "Best Song in a Motion Picture" and was nominated for an Academy Award for Best Song.
Pitney released a series of hit singles in the early 1960s, but was unable to withstand the British Invasion. He did, however, maintain a successful career in Great Britain and the rest of Europe. His last American hit was "She's a Heartbreaker" (1968), while he last hit the charts in the UK with 1989's duet with Marc Almond with "Something's Gotten Hold of My Heart".
In 2002, he was inducted into the Rock and Roll Hall of Fame.