“America” was inspired by a five-day road excursion Simon undertook in September 1964 with his then girlfriend Kathy Chitty. Producer Tom Wilson had called Simon back to the United States to finalize mixes and artwork for their debut studio album, Wednesday Morning, 3 A.M. Simon, living in London at the time, was reluctant to leave Chitty, and invited her to come with him, forgetting the album and spending five days driving the country together.

“America” is a song that “creates a cinematic vista that tells of the singer’s search for a literal and physical America that seems to have disappeared, along with the country’s beauty and ideals.” Art Garfunkel once described the song as “young lovers with their adventure and optimism”.

The narrator spends four days hitchhiking from Saginaw to join Kathy in Pittsburgh, where together they board a Greyhound bus to continue the journey. The narrator begins with a lighthearted and optimistic outlook (“Let us be lovers, we’ll marry our fortunes together”) that fades over the course of the song. To pass time, he and Kathy play games and try to guess the backgrounds of their fellow passengers. Over the course of their journey, they smoke all their cigarettes. Kathy reads a magazine before falling asleep, leaving the narrator awake to reflect on the meaning of the journey alone. In the final verse, the narrator is able to speak his true emotions to Kathy, now that she is sleeping and cannot hear or answer. “I’m empty and aching and I don’t know why” captures the longing and angst of the 1960s in nine simple words. The narrator then stares out the window “counting the cars on the New Jersey Turnpike.” Many other empty, aching, and lost souls are on the highway, each on their own journey alone even if someone is traveling with them. The soaring harmony lines and crashing cymbals create a powerful and poignant end to the song’s final verse: “They’ve all come to look for America.” Pete Fornatale interprets this lyric as a “metaphor to remind us all of the lost souls wandering the highways and byways of mid-sixties America, struggling to navigate the rapids of despair and hope, optimism and disillusionment.”

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