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American Pie" progresses chronologically from the "day the music died" until the late 1960s. In verse five, McLean mentions the Woodstock festival in 1969 and refers to "a generation lost in space." McLean also mentions Satan and the Devil to underscore his view that the 1960s was a time of debauch. The songwriter views the 1960s as being a generation "lost" to drugs. Music concerts and public events became spectacles and often erupted into violent protests. For instance, McLean refers to a concert the Rolling Stones played at, during which the Hell's Angels motorcycle gang overstepped their authority as chief security officers. McLean likens the event to a "sacrificial rite." Therefore, the songwriter describes the changes in American culture in Biblical terms, continuing to use imagery relating to death.

The title of the song is itself conveys the semiotics embedded in "American Pie." Pie is one of the only foods considered quintessentially American. The reference evokes mom's apple pie, an image of idyllic domesticity in the suburbs, of traditional gender roles, of sweetness, family, and the American Dream. The "day the music died" was the day that American woke up from its Dream. Gender roles were shifting rapidly so that women were no longer geared to be housewives. American culture seemed to be coming apart at the seams. The happy-go-lucky energy of the 1950s, captured in the songs of Buddy Holly, Richie Valens, and the Big Bopper, had died when those musicians perished in a plane crash. Those were the "good old boys" McLean refers to in the central refrain of the song. Likewise, when McLean writes about driving his "Chevy to the levee," he also uses another icon of American culture: the Chevrolet automobile.

During the 1960s a wave of events took place that would forever alter the character of the American Dream and of the American consciousness. The Vietnam War was by far the most significant, giving rise to a youth culture to a degree that had never before existed. Prior to the 1960s youth culture was a silent voice on the cultural landscape. Artists like James Dean were among the first to reveal the power of youth culture in America. His death, referred to in the third verse of "American Pie," is akin to the deaths of the three musicians mentioned at the beginning of the song. Youth culture became rebellious and highly political. Activism was a new trend that led to disturbing protest movements that were often mingled with musical concerts like Woodstock. The Kennedy assassination also signified the "day the music died," as did the infusion of radical politics into popular music. McLean mentions Marx in verse three to refer to the wholesale shifts in American lifestyle and culture.