The “most shocking moment” of Paul Simon’s career came in one 1990 song
Paul Simon was the songwriting force behind some of the most cherished folk rock songs ever played, the soulful notes of ‘Bridge Over Troubled Water’ and ‘The Sound of Silence’ continuing to highlight Simon’s timeless writing.
Alongside Art Garfunkel, they scoured the Great American Songbook and mined the material of the Everly Brothers for inspiration, eventually landing on their unique pop-adjacent hybrid sound.
Even at the height of Simon & Garfunkel’s success, Simon seemed unwilling to stand still creatively. While many songwriters would have happily spent decades refining a proven formula, he consistently searched for new sounds, rhythms and perspectives to challenge both himself and his audience.
But as 1986’s Graceland confirmed, Simon wasn’t only capable of penning those. On the heels of a crumbling relationship with both Garfunkel and ex-wife Carrie Fisher, the eclectic album stunned listeners. After listening to a bootleg of South African music, he flew to Johannesburg to record in the city. The result was a bold mix of pop, rock, and mbaqanga.
Graceland remains one of his most successful ventures to date, and although it was controversial – Simon had broken a cultural boycott of South Africa – his pivot to worldbeat sounds was a pleasant surprise for listeners who’d grown accustomed to his folkly output.
But then again, surprising people wasn’t exactly a career first. When onlookers dismissed Art & Garfunkel as a cheap imitation of the Everly Brothers, they set about proving them wrong and created a catalogue so unique that it genuinely was a pleasant surprise.
Simon recounted another instance where he’d shocked even himself on a song in Robert Hilburn’s biography, Paul Simon – The Life. During a discussion about his top ten of songs he’d written, naturally, classics like ‘Me and Julio Down By The Schoolyard’ appeared, but he made a point of reflecting on the comparatively lesser-known 1990 track, ‘The Cool, Cool River’ from The Rhythm of the Saints.
The album also looked to broader musical influences as he’d done on Graceland, featuring clear influences from West Africa and Brazil and often deeply conceptual lyrics. ‘The Cool, Cool River’ was unique in its use of a 9/8 time signature. It created a discombobulated sound, not egregious enough to sound off-beat but still a significant departure from the radio-friendly work of Simon & Garfunkel.
“I have no idea where it came from,” Simon confessed in The Making of Bridge Over Troubled Water documentary, “It came all of the sudden. It was one of the most shocking moments in my songwriting career,” he said. “I remember thinking, ‘This is considerably better than I usually write.'”
Simon has often shared how his unique songwriting process works and has it nailed to such a fine science that being surprised by the words that tumbled out of him for ‘The Cool, Cool River’ was a rarity. He would typically sit with his guitar, jotting down lyrics on a legal pad until a song took shape. A crucial tenet of this routine was doing it early in the morning when his mind was sharpest.
For Simon, songwriting has always balanced discipline and mystery. While routines and habits helped create the right environment, he understood that the most memorable ideas often arrived unexpectedly, beyond the reach of any formula.
But as the 1990 song proved, there’s always room to be surprised. “I really can’t explain it,” he told American Songwriter. “I don’t really know why an idea comes to me. But all of a sudden, an idea comes and from experience, I can intuit what something means when an interesting line pops up.”
That sense of surprise may be one of the reasons Paul Simon’s catalogue continues to feel so vital decades later. Rather than relying solely on technique or experience, he has always remained open to the possibility that a song might take him somewhere entirely unexpected. ‘The Cool, Cool River’ stands as one of the clearest examples of that creative spontaneity: a moment when one of popular music’s greatest songwriters briefly astonished even himself.
