yeah, yeah, we’ve disected American Pie enough times, but somehow I’ve missed why the death of Buddy Holly is so significant, apart from the lamenting of a fanboy. Is it only the way younger generations reacted to Lennon, Marley, Cobain, Joplin, Hendrix, Bonham, Moon, Morrison, Bolan or… whoever? Or is McLean trying to convey something deeper?
I can’t speak for Don McLean, but I remember the nation’s reaction to the death of Buddy Holly. It was a terrible shock, and there was a lot of grieving, but I don’t recall that anyone at the time felt that this was “the day the music died.” It’s not as if rock ‘n’ roll ceased to exist when Buddy Holly was gone.
One of Holly’s big hits was That’ll Be The Day (When I Die)
Buddy Holly was an incredibly prolific songwriter; I think he averaged 8-10 per year.
I was just going to say the same thing 
BTW, Don McLean has never revealed the meaning behind “American Pie”. Whenever he’s asked about it in interviews, his standard reply is that it’s up to the listener how to interpret it.
At school we used to have a game trying to guess who was who in the lyrics – the jester, I remember, was a big sticking point. I’ve heard it’s supposedly Bob Dylan, but somehow that’s never made sense to me 
Best explanation, the name “Jester” comes from the Dylan song Mr. Tambourine Man, which has the lines
And if you hear vague traces of skippin’ reels of rhyme
To your tambourine in time, it’s just a ragged clown behind
“Jester” and “clown” can have similar meanings.
The “coat he borrowed from James Dean” refers to the albim cover of The Freewheelin’ Bob Dylan, on which Dylan is wearing a red windbreaker similar to the one James Dean wore in Rebel Without A Cause
“A voice that came from you and me” refers to Dylan’s origins as a folk musician.
“While the King was looking down, the Jester stole his thorny crown,” always meant for me when Dylan played an electric set at the Newport Folk festival and pissed off the folkie crowd. The King of course, being Elvis. It’s also been explained as referring to Elvis’s decline in the popular music charts, and Dylan’s overtaking him on the record charts and suffering the side effects of fame and fortune that Elvis has undergone.
The line “the jester on the sidelines with a cast,” refers to a 1966 motorcycle accident which left Dylan badly injured.
His alternate response is “It means I never have to work again.”
Also, the crash didn’t just kill Buddy Holly, it also killed Ritchie Valens and the Big Bopper. So it was a real loss to the early Rock ‘n’ Roll, beyond just the death of Buddy Holly.
Look at what happened to American pop music shortly thereafter. It became the land of “teen idols”. Really crappy music dominated the charts until nearly the British invasion.
In general, there’s an inverse correlation with how much control the record labels have over “the industry” and the quality of the music. Buddy Holly, the Sun Record people and such started out and gained popularity outside the main labels. And rock’n roll was great.
But soon the big labels adjusted, co-opted some of the main stars (including Holly) and went back to bland pop stuff. Bobby Darren, Connie Francis kind of stuff.
In short, there was a period of about 4 years when the pop charts were dominated by some really terrible stuff. One can easily attach the Holly crash to the beginning of that period.
Well as Jodi said, it is about the loss of all three idols – the three men most important to the narrator (presumably McLean). The deeper “meaning” is tying the event to a loss of innocence and a catalyst of growing up for the narrator (McLean was 14 in '59) as well as a loss of innocence for much of the country too. It might seem trite or cliched considering we have passed through the list of dying idols that you cited (and many more), but in many ways this was the first one and a big one at that.
How 'bout we see what Mr. McLean himself said in response to a column of our Perfect Master.
That’s it, right there. Buddy’s death was a line of demarcation. The end of raw, unbridled, wildly innovative rock ‘n’ roll. There were other converging events, as well. Elvis went into the army, Jerry Lee Lewis scandalously married his cousin, and Little Richard quit rock ‘n’ roll to preach – all around the same time. Holly’s death was the last straw. It was the day the music died.
After that, the youth market was coopted by the suits at the record companies, who fed the people a bland pablum of teen idols, girl groups, and doo-wop. It took the Beatles hitting the US in '64 to break us out of that funk, and bring back some real rock ‘n’ roll. (In addition to performing their own songs, they covered a lot of songs from rock ‘n’ roll’s late-50s heyday.)
Or, as John Milner put it in American Grafitti:
“The Day the Music Died” might as easily be the Kennedy assassination – which also left a “widowed bride,” and which shattered our national innocence much more thoroughly.
I think it meant that rock music died for a while during the teen idol phase. However, the death of Kurt Cobain also helped finalize the dominance of hip hop over rock music.
Except that the good old boys are drinking whiskey and rye and singing “This’ll be the day that I die,” which echoes the lyrics to Buddy Holly’s song “That’ll Be the Day (That I Die).”
And then the song goes on with a string of references to Bob Dylan, the Beatles, the Rolling Stones, the Byrds, Janis Joplin, etc. The song is pretty clearly about the musical evolution of the 60s. And the death of the music again, at the end of the 60s.
Rock and roll has died many deaths and been reborn. At the end of the 50s (when Buddy died and Elvis joined the army). At the end of the 60s (when Janis Joplin died, the Beatles broke up, Hendrix died, Morrison died). Disco killed rock in the 70s before Punk and New Wave revived it.
It died again in the late 80s (at least as far as mainstream radio was concerned), when dance and rap and stupid-ass (IMO) hair metal were dominating the charts. I remember a Rolling Stone cover of the era asked “Can Jesus Jones Save Rock and Roll?” He couldn’t, of course. That took Nirvana and Pearl Jam a couple of years later.
Rock and roll is again dormant, but I wouldn’t dance on its grave if I were you. Ever seen Carrie?
I relate best to what Cave Mike said. I was 14 in 1959 too, and part of the shock was, like he said, that generation’s first loss of an idol. The next one I remember was Patsy Cline in 1963, and it seemed like everything went downhill after that.
Anyways, I remember some people saying at the time Buddy died that he was going “pop” (and losing his edge), after the release of I Guess It Doesn’t Matter Anymore and Raining in My Heart, which had a totally different sound – all those strings. Where were the Crickets? But they were perfect songs to play over and over while crying your eyes out.
All of this makes me wonder about how Mick Jagger’s death will effect people. Or Keith Richards, or Jimmy Page, or Pete Townshend, or Paul McCartney, or Ray Davies. Those will be dark, dark days for me, I can tell you that.
In addition to the losses already mentioned, Chuck Berry got put in prison for a time right about then. Something about crossing state lines with a 14 yr-old girl. There was just nothing left.
I was 16 the day the music died. I pretty much quit listening to the R & R stations and tuned my radio to country or blues. Hank Locklin, Marty Robbins and Kitty Wells were good on the country side, and Jimmy Reed, Lightnin Hopkins and B.B. King were doing some great blues tunes. The folk music scene was just getting started and there was some good stuff there, when you could find it.
I didn’t intentionally listen to the R & R stations again until The Beatles hit the scene.
spoke- already beat me to it, but I’m gonna include my sig line anyway…rock on!