Songwriter and recording artist
In his 20s, Holmes was a session musician (producing sessions, writing and arranging songs, singing and playing a few instruments), who wrote jingles and pop tunes (including for
Gene Pitney, the Platters, the Drifters and television's
The Partridge Family). As a recording artist, Holmes broke through with
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. His second, self-titled album led
Rolling Stone to compare him to
Bob Dylan in the sense of being an artist of unprecedented originality that commanded attention.
Holmes' production skills were also in demand during this period, and he took on this role for
Lynsey De Paul on her album "Tigers and Fireflies", which spawned the radio hit "Holiday Romance". That album also featured a song, the bluesy "'Twas", co-written by the two.
"Escape" was included on his fifth album,
Partners in Crime, and reached the
Hot 100 No. 1 Hits of 1979. The song hit #1 late December 1979, becoming the last song to top the pop chart in the 1970s. The song fell to #2 for the first week of January, 1980 and then rebounded to #1 the next week, making Holmes the only artist to ascend to the #1 spot with the same song in different decades. Another popular song on that album was "Him".
Holmes wrote a song for the band
The Buoys called "
Timothy," possibly the only top-40 song about
cannibalism. Holmes was not in the band, but did play piano on the track. He also wrote "Give Up Your Guns", "The Prince of Thieves", "Blood Knot", and "Tomorrow" for the band. "Timothy" charted at #17 and "Give Up Your Guns" at #84. In
1986 Holmes's composition "You Got It All" (sometimes called "You Got It All Over Him") was a hit single for
The Jets and later recorded by pop superstar
Britney Spears, featured in her internationally released version of
Oops!...I Did It Again (2000).
In the 1980s and 1990s, Holmes also played in cabarets and comedy clubs, mostly in New York City, telling often autobiographical anecdotes illustrated with his songs.