The Duality of Genius: Paul Simon’s Career Reflections on Success and Failure
Paul Simon is widely recognized as one of the most influential songwriters in American history, capable of bridging cultural divides and penning timeless anthems. However, a closer glance at his trajectory reveals a complex relationship with his own work, ranging from deep resentment toward some of his biggest hits to the sting of high-profile theatrical failures.
The Broadway Struggle: The Failure of ‘The Capeman’
While Simon found immense success in the recording studio, the Broadway stage proved to be a different challenge. His doo-wop Latin musical, The Capeman, lasted only 68 performances before closing.
The production was based on the true story of Salvador Agron, who murdered two teenagers in Hell’s Kitchen in 1959. Agron earned the “Capeman” nickname due to the black cape with red lining he wore during the crime. Several factors contributed to the musical’s failure:
- Artistic Control: Simon spent five years writing the score and insisted on maintaining complete artistic control, a move that deviated from standard Broadway practices.
- Creative Friction: Simon was vocal about his issues with the theatrical art form, which may have clashed with the demands of the medium.
- Expectations: After decades of chart-topping success, the project became a disappointment that Simon later admitted he tried to block out.
The Complex Legacy of Simon and Garfunkel
The partnership between Paul Simon and Art Garfunkel produced some of the most enduring music of the 20th century, yet it was fraught with tension. Simon has expressed a surprising level of resentment toward “Bridge Over Troubled Water,” noting that the hit record signaled the end of their professional relationship.
The emotional weight of their split is further captured in “The Only Living Boy in New York,” described as a bittersweet masterpiece that serves as a farewell to the duo. The depth of their complicated bond is evident in the fact that Simon wrote two specific songs about Garfunkel.
Musical Influences and Industry Perspectives
Simon’s approach to songwriting is rooted in a deep respect for those who paved the way. He has cited the Beatles as being “so far ahead” that they outmatched everyone else in the industry. He as well credited his favorite American songwriters for teaching his entire generation through their storytelling.
His perspectives on other icons are equally candid. Regarding Prince, Simon suggested that the artist’s legacy might be forgotten, though he added that Prince likely wouldn’t have cared about such a fate.
Personal Life and Creative Evolution
Simon’s personal relationships have frequently intersected with his creative process. His marriage to Edie Brickell significantly altered her own songwriting process, opening up possibilities she had not previously considered.

His romantic history also includes a notable relationship with Carrie Fisher. The two dated for six years and were married for two before divorcing after one year.
- The Capeman: A Broadway flop that ran for 68 performances due to Simon’s insistence on total artistic control.
- Relationship Strains: “Bridge Over Troubled Water” is viewed by Simon as a marker for the end of his partnership with Art Garfunkel.
- High Regard: Simon considers The Beatles the gold standard of songwriting.
- Personal Ties: His songwriting and personal life have been shaped by partners like Edie Brickell and Carrie Fisher.
Conclusion
Paul Simon’s career is a study in the pursuit of perfection. From the heights of global stardom to the “disappointment” of The Capeman, his journey reflects a musician who is never satisfied with the status quo. By embracing both the hits he resents and the failures he tried to forget, Simon continues to embody the belief that music should grow and mature alongside the artist.