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American Pie is McLean’s second album, his first, Tapestry, having been released to only moderate commercial success and acclaim in 1970. McLean was a protégé of Pete Seeger, having played with him in the 1960s. The album American Pie was intended as a unified work, as McLean has said that he was influenced by The Beatles' Sgt Pepper's album and envisioned American Pie to be a similar work. Believing that an artist's work should stand by itself, McLean generally did not offer explanations for his work's themes or meaning, though he did describe the title song as involving "a sense of loss". The album was dedicated to Buddy Holly, a childhood icon of Mclean's, and was released in 1971 on the heels of the '60s, the defining decade of McLean’s generation. It has a melancholy feel and rather sparse arrangements. At the time of the writing McLean’s first marriage was failing and the optimism and hopefulness of the1960s was giving way to the nihilism and hedonism of the 1970s.

The original United Artists Records inner sleeve featured a free verse poem written by McLean about William Boyd, also known as Hopalong Cassidy, along with a picture of Boyd in full Hopalong regalia. This sleeve was removed within a year of the album's release. The words to this poem appear on a plaque at the hospital where Boyd died. The Boyd poem and picture tribute do appear on a special remastered 2003 CD.

The title track contains references to the death of Buddy Holly (McLean being a 13-year-old paper-boy at the time ). The phrase "The Day the Music Died" was used by McLean on this song, and has now become an unofficial name for the event.

The third track and second single "Vincent" concerns the Dutch post-impressionist artist Vincent Van Gogh.

In one version of the story, the track "Empty Chairs" inspired Lori Lieberman to write the poem upon which the song "Killing Me Softly" is based.

"The Grave", originally a protest song against the Vietnam War, was covered by Wham! member George Michael in protest against the Iraq War in 2003.

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