Paul Simon Opens Up About His Biggest Career Regret

It’s easy to look at Paul Simon’s career and assume there are no loose ends. The songs hold up, the catalog runs deep, and the legacy feels settled. But even artists who seem completely in control of their work carry a few moments they wish had gone differently.

Simon has never been shy about acknowledging that not everything came together the way he hoped, especially during the final years of Simon & Garfunkel. While the music itself rarely disappointed him, the circumstances around it sometimes did. That distinction matters. For Simon, the regret wasn’t about songwriting—it was about timing, decisions, and missed chances.

Among those moments, one stands out more than most. It wasn’t a failed album or a forgotten track. It was a project tied to something outside music, something that quietly shifted the direction of a partnership that had already begun to strain.

Confidence Didn’t Come Overnight

Even with a song as enduring as “The Sound of Silence,” Simon didn’t immediately feel like he had everything figured out. Early albums carried a mix of brilliance and uncertainty, with traditional arrangements sitting beside original material. That contrast showed a young writer still testing his voice.

As the duo progressed, that uncertainty began to fade. By the time they reached Bookends, there was a clear sense of direction. The songwriting became sharper, and the themes more focused. It felt like a moment where both Simon and Art Garfunkel were fully aligned, at least musically.

But alignment in music didn’t always mean alignment in everything else. Differences in opinion—especially about the world outside the studio—started to creep in. Those tensions didn’t always show up in the songs, but they were there, building in the background.

The Film That Changed Everything

The turning point came with Catch-22, a project that seemed harmless at first. Art Garfunkel took a role in the film, which required him to spend long stretches away from recording sessions. That absence left Simon working more on his own, shifting the dynamic that had defined their partnership.

Originally, there were plans for Simon to be involved as well. But as the script evolved, his role was reduced and eventually dropped. What might have been a shared experience turned into something one-sided. It wasn’t just about acting—it was about separation, both physical and creative.

Looking back, Simon described the situation as something he tried to block out. Garfunkel’s time away didn’t cause the breakup on its own, but it accelerated what was already happening. The distance made it easier for both of them to drift onto different paths.

A Breakup That Felt Inevitable

By the time Bridge Over Troubled Water came together, the cracks were hard to ignore. There were disagreements over songs, including material Simon wanted to push further politically. Not everything made it through, and those creative differences became harder to smooth over.

At the same time, Simon was already moving toward a broader musical style. Songs like “El Condor Pasa” hinted at the direction his solo career would take. That evolution didn’t always fit neatly within the duo’s structure, especially as both artists began prioritizing their own ideas.

In hindsight, Simon has admitted that the breakup may have been unavoidable. Duos, by nature, tend to pull apart over time. Still, that doesn’t erase the feeling that things might have lasted longer under different circumstances. The regret isn’t about the music they made—it’s about the version of the story that never got the chance to play out.