(Credits: Far Out / Harry Chase, Los Angeles Times)
Sat 3 January 2026 19:36, UK
As the middle of the 1970s rolled around, Paul Simon was one of the most popular singer-songwriters in the world. Having achieved fame with Simon and Garfunkel in the 1960s, Simon was now knocking out solo hits like ‘Mother and Child Reunion’, ‘Kodachrome’ and ‘Love’s Me Like a Rock’. Those were all top-ten hits, but Simon still hadn’t nabbed a number one single since his days with Art Garfunkel.
That would change thanks to his 1975 album Still Crazy After All These Years. While ‘Gone At Last’ and the album’s title track were top 40 hits in America, it would be ‘50 Ways To Leave Your Lover’ that gave Simon his one and only number one solo hit. According to Simon himself, the song came in a flash one morning.
“I woke up one morning in my apartment on Central Park and the opening words just popped into my mind: ‘The problem is all inside your head, she said to me…’ That was the first thing I thought of,” Simon told the publication Rock Lives in 1975. “So I just started building on that line. It was the last song I wrote for the album, and I wrote it with a Rhythm Ace, one of those electronic drum machines so maybe that’s how it got that sing-song ‘Make a new plan Stan, don’t need to be coy Roy’ quality. It’s basically a nonsense song.”
Of course, Simon had some inspiration other than random divine intervention. His divorce from his first wife, Peggy Harper, was official in 1975, and a stunned Simon struggled to address the reality in his writing. The answer came in humour, which Simon tapped into while creating the ‘50 Ways To Leave Your Lover’ chorus.
Propelled by Steve Gadd’s iconic drum part, ‘50 Ways To Leave Your Lover’ finds Simon discussing his marital troubles with a new flame. Instead of dealing with the harsh realities that splitting up causes, Simon is told that keeping things simple is the best way to do it. Whether it’s slipping out the back, making a new plan, or dropping off the key, there are plenty of ways to free yourself.
‘50 Ways To Leave Your Lover’ became just one of Simon’s most iconic songs. Although it was a live staple, Simon soon added top 40 hits like ‘Slip Slidin’ Away’, ‘Late in the Evening’ and ‘You Can Call Me Al’ to his repertoire. Still, ‘50 Ways To Leave Your Lover’ would be Simon’s only solo number one hit of his career.
The “nonsense” continues
Perhaps the most nonsensical part of the song is not that it was just thought up as some kind of joke, but that Simon only bothers to share five ways to leave said lover. Simon sings, “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” and “Drop off the key, Lee, and get yourself free”.
While there is certainly a sense of underdelivering from Simon it perhaps links into his real feeling around the track. He didn’t care for it then, and there’s a good chance he doesn’t care for it now.
Check out ‘50 Ways To Leave Your Lover’ down below.
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