The Simon and Garfunkel Song That Captured the End of an Era

It’s not widely recognized that Paul Simon entered the pop landscape at roughly the same moment as Elvis Presley. Around 1956, as rock ‘n’ roll began captivating a new generation, Simon and his childhood friend Art Garfunkel were quickly swept up in its excitement.

The pair—later known as Simon & Garfunkel—even tasted early success as teenagers. Performing under the name Tom and Jerry, they scored what Simon would later describe as a “neighbourhood hit.” Though modest, it was enough to spark ambitions of a serious future in music. A few years later, their single ‘Hey Schoolgirl’ climbed to No. 49 on the charts, hinting at greater promise ahead.

However, that momentum faltered. The duo eventually split, pursuing university life and individual paths. Between 1957 and 1964, Simon wrote around 30 songs during his solo efforts—most of which failed to gain traction. The contrast between those discouraging years and their carefree early days, when even a single local radio play felt like a triumph, became stark.

Fate, however, had other plans. The pair reunited, and after years of struggle that nearly drove Simon out of music altogether, they achieved remarkable success. By 1970, Simon & Garfunkel had risen to extraordinary heights, following a path paved in part by their early idol, Presley. Their debut album, Wednesday Morning, 3 A.M., performed modestly on the charts. Still, the duo would go on to sell nearly 90 million records throughout the 1960s, becoming one of the decade’s most successful acts—just behind The Rolling Stones.

In later reflections, Simon even suggested that their appeal surpassed that of their British contemporaries. In a 1972 interview, he remarked that Simon & Garfunkel were “a much bigger phenomenon… to the general public” than the Rolling Stones. Yet, despite this commercial peak, their partnership was nearing its end.

A Song Born from Distance and Doubt

By the late 1960s, success had brought strain. Garfunkel began exploring acting, landing a role in Catch-22, while Simon’s own involvement in the project was cut. Left behind in New York, Simon expressed his frustration with self-deprecating humor during a 1969 concert, joking about being overshadowed by his partner’s new career.

Beneath the humor, however, was a sense of isolation. While Garfunkel pursued opportunities beyond music, Simon remained focused on songwriting, feeling increasingly sidelined within their partnership.

Writing Through Bittersweet Emotion

Out of this emotional tension came ‘The Only Living Boy in New York’. The song captures Simon’s conflicting feelings—resentment mixed with genuine affection and pride for his friend.

In the track, Simon addresses Garfunkel (his “Tom”) with a tone that is both tender and resigned, wishing him well while quietly acknowledging the growing distance between them. At the same time, Simon reflects on his solitude in New York, retreating from public scrutiny and seeking peace amid success.

Lines that emphasize small comforts and quiet optimism contrast with the underlying sense of abandonment, giving the song its distinctive emotional depth. Garfunkel’s ethereal backing vocals further enhance this feeling, symbolizing both presence and absence at once.

A Farewell in Disguise

Ultimately, the song stands as a poignant meditation on change, friendship, and separation. It captures a moment when success could not mask the personal distance growing between two lifelong collaborators.

In essence, ‘The Only Living Boy in New York’ functions as a gentle, heartfelt goodbye—Simon’s reflective send-off to Garfunkel. A farewell from “Jerry” to “Tom,” filled with both melancholy and grace.