The plane crash occurred in 1959, which would have made Don McLean (b. October 2, 1945) thirteen and a half years old at the time.
I can still remember how that music used to make me smile
And I knew if I had my chance
That I could make those people dance
And maybe they'd be happy for a while
Don dreams of entertaining people as a musician, specifically as a rock and roller ("that music").
But February made me shiver
With every paper I'd deliver McLean was indeed a paperboy on the outskirts of New York City, and would have been delivering on the day of the crash, which was a Tuesday.
Bad news on the doorstep
I couldn't take one more step
I can't remember if I cried
When I read about his widowed bride
Buddy Holly was survived by his wife of only six months, Maria Elena Santiago Holly, who was pregnant with his child (which she miscarried after hearing the tragic news).
But something touched me deep inside
The day the music died
McLean uses the phrase "the day the music died" throughout the song as a metaphor for the death of his innocence, not necessarily rock in general. In his own words, it was "...an attempt to describe a certain loss I felt in American music. Buddy Holly's death, for me, was a symbolic death... The music never dies though, and all I was saying was that people lack the basic trust to believe the music will happen again."