By 1975, Paul Simon's marriage to his first wife, Peggy Harper, had come to an end, and it was this personal setback that drove him to write many of the songs on "Still Crazy After All These Years," which he released in October of that year. According to The Independent, Simon's songwriting during this period was driven by the struggles that baby boomers were going through as young adults, and as a 33-year-old man (34 at the time of the album's release) who had just split from his wife, he could certainly relate to those struggles. As such, when compared to the rest of the album, "50 Ways to Leave Your Lover" was definitely less serious.

Given the lyrics of "50 Ways" and the fact he wrote it following the breakdown of his marriage, it's easy to assume that the song is about Peggy Harper. However, Simon has been notoriously cagey when asked about who or what inspired the tune, and he has claimed that Peggy was not the "lover" in the song's title. Instead, it was another person named Harper — the couple's son, Harper Simon — who served as the catalyst for its rhyming lyrics.

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