Here's my take on the song:
Stanza I "A long, long time ago...
I can still remember
How that music used to make me smile."
The birth of Rock'n'Roll. Dance music. Performer not too far separated from the audience.
Stanza II "But february made me shiver
With every paper I’d deliver.
Bad news on the doorstep;
I couldn’t take one more step."
The death of Buddy Holly symbolizes the death of Rock'n'Roll as an underground, noncorporate phenomenon. "The day the music died" is the day when music is no longer communal property but becomes a commercial product.
Refrain: The speaker says goodbye to the American innocence of the multiple small labels, indie musicians of the Rock'n'Roll '50s. He drives his chevy to the levee and thinking like Leadbelly wants to jump into the river and drown. He morphs Buddy Holly's upbeat put-down song "That'll be the Day (That I Die)" into a dirge in which "Miss American Pie" (Miss American plus Apple Pie) has become what William Carlos Williams called the "pure products of American [gone] crazy." Like Leadbelly who sings about having a "great notion to jump in the river and drown," our singer drowns his sorry with cheap rye whisky and turns Holly's "That'll be the day" into "This'll be the day that I die."
Stanza III This Stanza seems most rooted in personal memory as the speaker recalls the late fifties doo-wop and r-n-b dance music craze (and the whole "black music" is the "Devil's music" controversy of nascent rock-n-roll.) Memories of high school gym dances in the lonely spaces of America seem like something out of Kerouac. Something seeking articulation that lies beyond the simple words of Monotones 1959 hit "The Book of Love."
Refrain
Stanza IV The speaker ain't so happy with what has replaced the innocent, honest and yet undeniably sexual energy of the first wave of rock'n'roll of the 1950s (the Golden Era). Ten years later from Buddy Holly's death, we have the nihilistic faux-r'n'b of the Rolling Stones (grown fat with green moss of big corporate bucks--certainly not flying around in Cessnas like Buddy). Dylan (a pure product with an authentic voice that "came from you and me") is out of the picture even though he had sung for the "king and queen" (his tours to England documented in "Don't Look Back, but also his anti-establishment stance in the corporate world of CBS records, who had "bought" and castrated the original "King" of rock-n-roll Elvis). The jester (think "Jokerman" over a decade earlier) steals the rock icon's messianic crown perhaps without realizing the cost of the theft (having to play pop prince/messiah to an audience that wants easy answers he cannot in good conscience give them). As those answers aren't so easy n typical Dylanesque fashion (or Lewis Carroll) "the courtroom is adjourned" and "no verdict is returned" (a couplet that seems derivative of the upside-down world of indeterminacy and injustice of Dylan's "John Wesley Harding" (1968).
The Beatles, another pop phenomenon like the Stones who have aped early rock-n-roll and turned it into a global commodity, have realized that they too have been caught in a capitalistic web of their own making. So John Lennon (like his homophonic revolutionary predecessor Vladimir Lenin) reads Karl Marx but cannot lead an authentic cultural revolution. Hence the quartet (Beatles in Sgt Pepper mode) "practice in the park," but are really only spinning their revolutionary wheels. The real revolution died the day the music died.
Stanza V: The Beatles dream of "All You Need is Love" has descended into its own opposite: the nightmare vision of Manson's "Helter Skelter". The Byrds (America's "answer" to the Beatles) can do no more to end the oppositional us-or-them/hippie-straight/capitalist-communist Cold War fallout shelter mentality that "authentic music" might have "thawed out." Instead the reference to the song "Eight Miles High" ("falling fast") relates not only to censorship by the corporate powers-that-be (that keep the birds and the jester on a leash), but also to the failure of the drug culture to provide a breakthrough in enlightenment. Dylan, who might have made some sense of the turmoil of the 1968 riots and social upheaval, is sidelined from his motorcycle accident and general disengagement with providing "public" answers to seemingly insolvable social problems of latter-day finance-capitalism in its death throes (symbolized by the meaningless football(?) game which descends into chaos in which the apparently military-style marching band "takes the field" much as US Military troops took and lost ground in Vietnam as reported on the Nightly News as if reporting on the lastest football games). The Sergeants playing a marching tune is another reference to the Beatles (ala Sgt Pepper) which provides a false sense of cultural moment (rock as art), but ultimately as a moment missed. You can't beat General Westmoreland and Nixon with song and dance. Or fancy silk shirts and psychedelic gew-gaws.
Stanza VII: The generation "lost in space" (from the TV show as well as hypnotized by the costly useless priapic space race to the moon) are all in one place in Woodstock--but later at Altamont (where Jack Flash--Mick Jagger as the demonic rock-star as Hitlerian rabble-rouser puppet who ultimately cannot control the primal forces he rouses and, hey, folks get murdered at a rock concert--who woulda thought? Would this have ever happened at a Buddy Holly show? Music has become stadiums and power and mass audience--the intimacy and connection of the original rock-n-roll performance has died. The intimacy of the seduction has become the gangbang.
Stanza VIII: The girl who "sang the blues" may be Janis Joplin--another victim to what Ray Davies called the Powerman entertainment business as well as her own bad habits engendered by the lack of authenticity in the rock star persona no one can live up to. The corner music stores are gone--product is being pumped through to big-box vendors. Commodification is all but complete. The speaker gets a bit maudlin (or Paul Simonesque) with children screaming/poets dreaming, but the breaking of the church bells is symbolic of the loss of connection between a spiritual need to make a "joyful noise" or alternatively "sing the blues"--rather than go through the motions in which music becomes a mechanism of crowd control and corporate earnings. Our last free gift of the soul has been bartered away for 30 pieces of silver. The money-changers have taken over the temple. The holy trinity (humanized--"the three men I admire most--in the ecstatic urge and spiritual connection of performer and audience) has been destroyed for this generation. They've headed for the coast (west to LA or east to NYC, but either way the prognosis is not strong for a cultural rejuvenation that will allow music to serve as a guide for people to seek authenticity in their lives and spiritual power from the rhythms and lyrics of the songs.