Paul Simon wrote this song about his partner Art Garfunkel going to Mexico to act in a movie called Catch-22, which was directed by Mike Nichols, who gave Simon & Garfunkel a big boost when he featured their songs in his 1967 film The Graduate. Simon was also going to be in the film, but Nichols cut his part, which separated the duo. Garfunkel spent months working on the film while Simon returned to New York, where he toiled away on the Bridge Over Troubled Water album. He expresses his frustration in this song: "Here I am, the only living boy in New York." Simon sent letters to keep in touch with Garfunkel and update him on the album's progress. Up to that point, the pair had always partnered musically and shared a bond, which was now breaking. Simon & Garfunkel split up after the album was released; Paul recorded as a solo artist, and Art pursued his acting career.
Regarding the lyrics, "Tom get your plane right on time. I know that your eager to fly now," before the folk duo became famous, they were known as Tom and Jerry. Tom was Art's stage name, so this line symbolizes their increasing need for musical and personal freedom.
In a 1990 interview with SongTalk magazine, Simon said: "I liked the 'aaahhhs,' the voices singing 'aaah.' That was the best I think that we ever did it. It was quite a lot of voices we put on, maybe twelve or fifteen voices. We sang it in the echo-chamber."
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