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Paul Simon wrote this song about his partner Art Garfunkel going to Mexico to act in a movie called Catch-22. Art was missing a lot of recording dates while trying to kick off his acting career, and Paul was hinting at a breakup. The duo did indeed split up after the album was released.
Regarding the lyrcis, "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."
Simon & Garfunkel split up after this album was released. Paul recorded as a solo artist, and Art pursued an acting career.
This was used in the 2004 movie Garden State. Zach Braff, who wrote and directed the movie, thought the song worked perfectly to convey the loneliness of a character. Simon & Garfunkel rarely license the song, but they let Braff use it for a greatly reduced fee after seeing the scene. (thanks, Denise - Santa Clarita, CA)
The session musician Joe Osborn played an 8-string bass on this track, which the album's producer Roy Halee said was the featured musical element of the song. Years later, when Osborn tried to relearn his part to demonstrate it, he realized it was very difficult to reproduce live, as Halee spliced together various takes for the recording.
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