Written after Simon's divorce from first wife Peggy Harper, the song is a mistress's humorous advice to a husband on ways to end a relationship. The song was recorded in a small New York City studio on Broadway.
"50 Ways to Leave Your Lover" was Paul Simon's biggest solo hit and broke in the US in late 1975. It hit number one on the US Billboard Hot 100 on February 7, 1976 (his only number one on that chart as a solo act), soaring from number ten the previous week, and remained there for three weeks; it topped the adult contemporary chart for two weeks. Overseas, on the UK Singles Chart, the song reached number 23 in January 1976. It was certified gold on March 11, 1976, and remained a best seller for nearly five months. Billboard ranked it as the No. 8 song of 1976.
Covers, parodies, and other notable versions
Dinah Shore performed the song on an episode of The Carol Burnett Show in the 70s
The Jacksons performed a parody of the song in their TV show, involving humorous sketches that showcased the fifty ways to leave one's lover, announcing them in a similar way to Simon's lyrics, rhyming an activity with a man's name.
The Muppets covered the song when Paul Simon appeared on that show. When appearing, Simon himself did a parody on the title when saying that there must be "50 ways to love your lever."
Eminem used a sample of the first verse of "50 Ways to Leave Your Lover" in his song "Murder, Murder".
Brad Mehldau covered the song on the album Day is Done (2005).
WABC-AMDJDan Ingram produced an edited version of the song that shuffled the names around and disrupted the rhyming couplets: the lyric "Slip out the back, Jack" was edited to be "Slip out the back, Stan", and so on.