Chorus, continued

Them good old boys were drinkin' whiskey and rye
Singin' "this'll be the day that I die,
This'll be the day that I die."

The bottles are raised to the good old days, as "them good old boys"* of Lubbock, Texas mourn the death of their favorite son, Buddy Holly; these figures could also symbolize a more naïve view of the world. But most significantly, "This'll be the day that I die" is a rewording of the line '''Cause that'll be the day when I die" from the chorus of Holly's hit That'll be the Day, in which the singer fears the worst should his love leave him: for the narrator, his love has left him, and this is McLean's way of both mourning the death of that music and way of life, and pointing to Holly as his symbol of it.

•   •   •

So "Miss American Pie" represents a simpler, more innocent time in American life, but that time has passed—she is no longer with him. To quote Buddy Holly:

You say you're gonna leave
You know it's a lie
'Cause that'll be the day when I die.

*The original inspiration for the chorus of American Pie may well have come from a little known incident that is purported to have occurred in McLean's youth: A bar called The Levee in his hometown of New Rochelle, NY had closed during McLean's early adult years, forcing him and his drinking buddies across the river to Rye, N.Y. for refreshments. "Drove my Chevy to the Levee but the Levee was dry" would then take on a more prosaic meaning, as "them good old boys" would be drinking whiskey in Rye. I have chosen to go with a more symbolic interpretation of the chorus, but this idea seems to fit too, albeit on a much more personal level. This story has been examined and supported well by Mark Jordan, and can be investigated further by visiting his site here.