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."
This song was addressed during a screening of the Simon & Garfunkel documentary Songs of America. At the screening, Garfunkel said, "I had Paul sort of waiting: 'All right, I can take this for three months. I'll write the songs, but what's the fourth month? And why is Artie in Rome a fifth month? What's Mike [Nichols] doing to Simon & Garfunkel?' And so there's Paul in the third month, still with a lot of heart, writing about, 'I'm the only living boy in [New York]. You used to be the other one."
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.
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.