You wouldn’t know it based on the type of music I usually talk about around this place, but I went through a phase in my late-high-school/early-college years when I was simply mad for the stuff that’s usually categorized under the catch-all term “oldies,” i.e., the early rock-n-roll artists of the 1950s, the girl groups of the mid-1960s, and the Motown sound and blues-influenced hard rock of the later ’60s. For a while, it was like I was trying to make myself into an honorary Baby Boomer or something.

Oldies music was somewhat resurgent at the time, turning up in popular movies like Back to the Future and Dirty Dancing, and on television shows such as The Wonder Years and some others you probably don’t remember, and of course it was used in all kinds of commercials that were cynically targeted to our nostalgic parents (just like the commercials of the last decade have been leveraging the Awesome ’80s to lure we thirtysomethings into Burger King or whatever). But for me, the appeal of this genre was the same things that drew some of my peers to punk or obscure college-radio alternative bands: it was refreshingly different from the stagnating pop scene of the late ’80s, and it was sufficiently esoteric that liking it was an easy way of declaring my individuality. It was also a vast, unknown territory with an intricate and interconnected history that I could explore and lose myself in and become insufferably opinionated about, which are, of course, the fundamental elements of any fannish concern. It didn’t hurt that my old Ford Galaxie, my beloved Cruising Vessel, had a stock, AM-only radio and oldies were about the only kind of music you could find with that thing. And of course a lot of that music is just plain good. There’s a reason why songs by The Four Tops and Roy Orbison are still heard in movie soundtracks 40 years after they were recorded, and it’s the same reason why certain tunes by Sinatra and the Glenn Miller Band live on, too. Because they managed to express something so perfectly that they continue to work for us, despite the passage of time. I hope we never change so much as a culture or a species that they cease working.

Anyway, there were a lot of artists I enjoyed and admired during my oldies fanboy phase — Sam Cooke, Fats Domino, The Supremes, The Platters, The Drifters, Chuck Berry, the aforementioned Orbison — but my favorite was a guy who’s possibly more famous for his untimely death than for anything he did while he was living, which is one of the great shames of music history. I’m talking about a skinny kid from Texas named Buddy Holly, who died in a plane crash 50 years ago today.

I’m sure you all know this story, considering how many movies have featured some version of it: Holly and two other musicians — Ritchie Valens of “La Bamba” fame and J.P. “The Big Bopper” Richardson — were planning to fly to their next tour stop on a small chartered plane, but the plane went down in a corn field only moments after taking off on a snowy night, killing the three and their pilot, whose name no one ever remembers. (It was Roger Peterson, for the record.) At 28, Richardson was the oldest of them; Holly was only 22, Peterson 21, and Valens, the baby of the group, was still three months shy of his 18th birthday. The event was famously commemorated by ’70s singer-songwriter Don McLean as “the day the music died,” and in the movie American Graffiti, the character John Milner laments that “rock and roll’s been going downhill since Buddy Holly died.” (The movie is set in 1962, a mere three years after the plane crash.) While I wouldn’t go as far as Milner, there’s no question that rock music lost someone deeply significant — or at least potentially significant — that day.

Holly is one of those great “what-if?” stories of popular culture. Like James Dean, another immense talent cut down early by a stupid accident, you always wonder what he might have accomplished is only he’d lived a little longer. I intend no disrespect to J.P. Richardson or Ritchie Valens, but it had to be obvious even in ’59 that The Bopper was a mere novelty act, and Valens simply hadn’t recorded enough music to allow a guess at whether he would’ve long endured. But Buddy Holly left behind a string of hit songs that seemed to be growing in sophistication with each passing one, hinting at greatness yet to come: “Oh Boy,” “That’ll Be the Day,” “Maybe Baby,” “Not Fade Away,” “Rave On,” the lovely “Everyday,” and, of course, “Peggy Sue,” which is one of those perfect, timeless tunes I mentioned earlier. It just never gets old.

It wasn’t merely that he recorded some good songs, though. Holly was a rarity in those early days of rock in that he wrote or co-wrote most of his own music, and he was interested in producing as well, things we take for granted now but were downright groundbreaking in the late 1950s. It’s not inconceivable that, had he lived, Holly might have produced a landmark album along the lines of Sgt. Pepper — something based in rock-n-roll but which rises above it in ambition and vision — years before The Beatles thought of it. (I don’t think it’s a coincidence that The Beatles and The Rolling Stones both idolized Holly and recorded some of his music.) And Holly, like Elvis Presley a couple years before him, was a trailblazer in race relations during those segregated times. While Elvis brought the sound of black music to white audiences, Holly worked in the opposite direction, famously winning over a skeptical African-American audience at the Apollo Theater in 1958.

He was, in short, much cooler than his trademark horn-rim glasses might have suggested. My youthful obsession with Holly came in part from liking his music, and partly from the fact that I was pretty close at the time to his age when he died and I found that similarity enticingly tragic and eerie. But the thing that really captivated me then and now was the question of what might’ve been. I’m convinced he had the potential to become the first true rock-n-roll artist, rather than simply a star. But of course, we’ll never know for sure. Holly would’ve been 72 years old now, something as hard to imagine as a senior-citizen Elvis or James Dean in a retirement home. I like to think he’d still be around, an elder statesman like Frank Sinatra became, still recording and experimenting, still entertaining. Most of all, still rocking.

At least we still have “Peggy Sue.” Here’s Buddy and his band, The Crickets, performing it live on television in 1958; the hostess who introduces them is condescending as hell and the kids in the background are apparently all on Valium, but it’s a good performance. Moreover, it appears to my eye to be a real performance, instead of the lip-synched stuff you usually see in old American Bandstand clips:

Yeah, that’s the stuff, baby. Makes me want to go get the old Cruising Vessel out of storage and warm up that AM radio…