Credit: Far Out / Harry Chase, Los Angeles Times
Sun 11 October 2026 11:01, UK
Very few people in the world can sit back at the end of the day and objectively judge their work. Whether you are laying bricks or laying tracks, accurately reflecting on your work is a task our subjective minds are often completely incapable of. That’s why, though many artists might fight it, you need a label to step in every so often, as Paul Simon found out.
Noodling away in the studio, lost in the musing of your own mind, it can be easy to be completely lost in a thicket of trees and unable to see the bigger picture of the five-million-copy-selling wood. The truth is, there’s no right way for anyone to conceive of a hit in the world of rock and roll.
Although many power pop bands have made songs that sound ready for primetime across their entire career, some acts manage to have their biggest hits with songs that defy the laws of convention for what a true rock and roll classic is supposed to be. And while Paul Simon is the last person that anyone would think of as making some avant-garde music in his spare time, he knew when some tracks didn’t have what it took to be major successes.
But Simon was never the most commercial entity, even when looking at Simon and Garfunkel. Their harmonies may have been absolutely beautiful whenever they sang together, but no one was going to listen to every track off of Wednesday Morning 3 AM and think that they were ready for the big time outside of ‘The Sound of Silence’, and even that one had to be fed through a folk-rock lens for most people to stomach.
When listening to Simon’s solo career, though, there was a lot more room for him to take risks. He had a lot to say when he was with Garfunkel, but hearing him delve into different styles of music on records like Graceland was far more interesting than listening to the traditional folk tunes he was known for. Those were certainly great, but it was time for him to search for new sonic spaces to work in.
“‘Kodachrome’ I thought was a hit. It sounds like a pop song. All the other ones sound odd. ‘50 Ways To Leave Your Lover.’ They didn’t sound like what the hits sounded like at the time.”
Paul Simon
And while going to South Africa during apartheid was a risky move, it paid off in dividends once people saw what both genres of music could do when they understood each other. Outside of the world of folk-rock, Simon was also an avid fan of everything from classical music to jazz, and when listening to the way that he wrote songs on Still Crazy After All These Years, he was more than willing to try out something a little bit weirder.
This was by no means a Steely Dan record in terms of jazz-rock perfection, but the downtempo material and the strange chords have a more mellow groove than anything going on at the time. Even if it was far from reaching the same excitement levels as what Led Zeppelin had been doing, there was something about ‘50 Ways to Leave Your Lover’ that made everyone relate to what Simon was saying.
Which shocked the hell out of Simon when he first started writing the tune, saying, “‘Kodachrome’ I thought was a hit. It sounds like a pop song. All the other ones sound odd. ‘50 Ways To Leave Your Lover.’ They didn’t sound like what the hits sounded like at the time. Radio was more open to things that weren’t exactly what every other hit was.” And it’s not like he’s exactly wrong, either.
Listening to the downtempo ways that he starts the verses, no chord is repeated more than once, either involving him playing extensions on the chords or throwing in different notes that would have sounded so out of place if they appeared on an Osmonds record or one of The Carpenters’ hits from around that time. No one should ever count out the power of a good chorus, and when this one rolls around, it’s easy to forget all about the complex stuff and sing along with Simon.
The chorus almost feels as though it wandered in from a more straightforward song. After the verses quietly examine the end of a relationship, Simon begins firing off comic names and simple instructions: Jack slips out the back, Stan makes a new plan, and Gus apparently requires very little discussion.
The title promises 50 escape routes, but the lyric supplies only five, making the whole thing closer to a joke than a practical guide. That sudden simplicity was not a retreat from the sophistication of the verses. It was the device that made them commercially viable. Simon gave radio audiences a phrase they could remember after one listen, then smuggled all the unusual harmony and emotional uncertainty around it.
But maybe ‘50 Ways to Leave Your Lover’ is a lesson for any songwriter. Most people play to the lowest common denominator of fans when making something simple, but perhaps the public has a more refined taste than everyone initially thought. Now it’s up to the rest of the musicians to find the right way to translate those complex tunes into something palatable.
