He scored a kooky top 40 single on the Billboard Hot 100 in 1959 with the novelty hit "The Mummy," under the pseudonym Dor. McKuen wrote the song, which was credited to Bob McFadden and Dor. McKuen notched a Hot 100 hit under his own name with "Oliver Twist," which peaked at No. 76 in 1962.
Another song McKuen wrote, "Jean," became a No. 2 Hot 100 hit for Oliver in 1969 (stuck for two weeks in the runner-up slot behind The Archies' "Sugar, Sugar"). "Jean" -- written for the film The Prime of Miss Jean Brodie (1969) -- garnered McKuen an Academy Award nomination for best original song, his first of two Oscar nods. McKuen landed a second Academy Award nomination a year later, for original song score, for his work on A Boy Named Charlie Brown (1970).
McKuen also wrote such songs as "Seasons in the Sun" (No. 1 on the Hot 100 for Terry Jacks in 1974) and "Love's Been Good to Me" (No. 8 on Adult Contemporary for Sinatra in 1969). The latter song was from Sinatra's A Man Alone album, comprised entirely of songs written by McKuen for Sinatra (at Sinatra's personal request).
McKuen explained on his website in 1999: "You can imagine how excited I was when Frank Sinatra asked me to write an original album for him. What could possibly be nicer, more flattering and challenging than being commissioned by the world's most inventive and popular singer to write and compose something, let alone a whole album, for HIM. It was like winning the Nobel and the Lottery on the same afternoon. Scintillating and scary." He added, "I think the result of our collaboration speaks and sings for itself. Both of us were very satisfied with the album and the making of it created a bond that even his death a year ago couldn't break."
A Man Alone peaked at No. 30 on the Billboard 200.
Another McKuen tune, "If You Go Away," was based on Jacques Brel's "Ne Me Quitte Pas," with English lyrics by McKuen. The song has been recorded by an array of A-listers, including Glen Campbell, Sinatra, Neil Diamond, Dusty Springfield and Cyndi Lauper. It was a No. 10 hit on the Adult Contemporary chart for Damita Jo in 1966. Barbra Streisand recorded a version of the song for her 2009 album Love Is the Answer, which debuted at No. 1 on the Billboard 200.
McKuen also -- perhaps surprisingly -- has a co-writing credit on Madonna's "Drowned World/Substitute for Love," which samples the McKuen-penned "Why I Follow the Tigers" by San Sebastian Strings. The first vocal you hear in the Madonna track is a man saying "you see," which is a sample from "Why I Follow the Tigers." After the release of "Drowned World," McKuen clarified his writing credit on the song, saying that it wasn't a mere sampling issue. He wrote on his website: "'Drowned World' follows the plot line of 'Tigers,' which is why Anita [Kerr] and I receive co-author credit on the song, and not merely 'sampling mention.'" He also said: "I think Madonna's lyric is terrific (and by the way so are the royalties generated by the track)."
"Drowned World/Substitute for Love" reached No. 10 on the Official U.K. Singles Chart, and was lifted from Madonna's Grammy Award-winning Ray of Light album (No. 2 on the Billboard 200, No. 1 on the Official U.K. Albums Chart).