In his 20s, Holmes was a session musician (producing sessions, writing and arranging songs, singing and playing a few instruments). In March 1970, he and Ron Dante (The Cuff Links and The Archies) recorded "Jennifer Tomkins" for release on their second album, The Cuff Links.

During the recording of that album, Dante was prohibited by the studio that produced The Archies from any involvement in new recording ventures and was forced to drop out of The Cuff Links. Holmes finished the project and released "Jennifer Tomkins" separately under a different studio name, The Street People. The song was on the Billboard (magazine) pop charts for 15 weeks, beginning January 3, 1970, reaching a peak of 36. A follow up single called "Thank You Girl" reached 96 on the Billboard pop charts in April 1970.

As a recording artist, Holmes broke through with his first album, 1974's Widescreen on Epic Records, which introduced him as a presenter of highly romantic, lushly orchestrated "story songs" that told a witty narrative punctuated by clever rhymes and a hint of comedy. Barbra Streisand discovered this album and asked to record songs from it, launching Holmes on a successful career. She then used some of his songs in the movie A Star Is Born. He also arranged, conducted and wrote songs on her 1975 album, Lazy Afternoon and five of her other albums. Holmes' second, self-titled album led Rolling Stone to compare him with Bob Dylan in the sense of being an artist of unprecedented originality that commanded attention.

"Escape" was included on Holmes' fifth album, Partners in Crime, and reached the Hot 100 No. 1 Hits of 1979. Another popular song on that album was "Him", which peaked at number 6 on the Hot 100. He had another top-40 hit with "Answering Machine". In 1986, Holmes's composition "You Got It All" (sometimes called "You Got It All Over Him") was a top 3 hit single for The Jets and was later recorded by pop superstar Britney Spears and featured in her internationally released version of Oops!… I Did It Again (2000). He also produced two songs for singer Judy Collins that appeared on her album Sanity and Grace.

This song hit #6 on the charts back in 1980? How about today?

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