Paul Simon has enjoyed a long and successful solo career since parting ways with Art Garfunkel in 1970, but he’s only had one No. 1 hit on the Billboard Hot 100. That song was his classic breakup tune “50 Ways To Leave Your Lover,” which topped the chart 50 years ago.
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The track was the second single released from Simon’s fourth solo studio album, Still Crazy After All These Years. “50 Ways To Leave Your Lover” took over No. 1 on the Hot 100 from Ohio Player’s “Love Rollercoaster.” It spent three weeks on the top of the chart before being replaced by Rhythm Heritage’s “Theme from S.W.A.T.”
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“50 Ways To Leave Your Lover” features Simon singing from the perspective of a guy who’s struggling to figure out how to break up with his romantic partner. In the tune, he’s talking to a female friend, who gives him advice on various ways to go about it.
The tune actually only mentions five ways to leave a lover, each suggestion humorously rhyming with a man’s name. The five ways are: slip out the back, Jack; make a new plan, Stan; you don’t need to be coy, Roy, just set yourself free; hop on the bus, Gus; drop off the key, Lee, and get yourself free.
Simon wrote the song around the time of his divorce from his first wife, Peggy Harper. It’s not known, though, if that breakup directly influenced the tune. In a 2023 interview with Howard Stern, Paul explained that he came up with the lyrics to the chorus while he was teaching his then-young son, Harper, about rhymes.
More About the Making of “50 Ways To Leave Your Lover”
“50 Ways To Leave Your Lover” features an iconic repeating drum pattern that Simon’s longtime drummer, Steve Gadd, created.
As Paul explained during the interview with Stern, he’d started writing the song with a drum machine. When he played the tune for Gadd accompanied by the machine, the drummer made a suggestion.
As Simon recalled, “Steve says, ‘I was in the Army Corps of drummers, and part of what we had to learn were these parade drum things. So I would practice these kind of [military] beats.’ He said, ‘What about that?’ And I said, ‘Yeah, sure. Let’s try it.’”
Paul noted that the part Gadd played “is one of the most-sampled drum parts.” He added, that Gadd was “maybe the premier drummer of my generation, or certainly one of them.”
“50 Ways To Leave Your Lover” also features backing vocals by Phoebe Snow, Patti Austin, and Valerie Simpson. Simon, of course, played acoustic guitar on the song. Other musicians who played on the track included John Tropea and Joe Beck on electric guitar, Ken Asher on organ, and Tony Levin on bass.
“50 Ways To Leave Your Lover” Sales Info and Accolades
“50 Ways To Leave Your Lover” was certified Gold by the RIAA for sales of 500,000 copies in the U.S. In 1977, the song was nominated for a Record of the Year Grammy, but lost to George Benson’s “This Masquerade.”
The Still Crazy After All These Years album, meanwhile, topped the Billboard 200 in December 1975. It’s Simon’s only solo album to reach No. 1 on the chart. Still Crazy After All These Years also was certified Gold for U.S. sales of 500,000 copies. In 1976, Still Crazy After All These Years won Grammys for Album of the Year and Best Pop Vocal Performance, Male.
(Photo by Michael Putland/Getty Images)
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