Okay, let’s suppose for a moment that the Winter Dance Party tour had been completed as originally scheduled, instead of crashing to a halt in the middle of an Iowa cornfield fifty years ago. What would have happened? Let’s speculate.
Buddy Holly had just split from the Crickets and was attempting a solo career which at the time really wasn’t going anywhere. He did, however, have a couple of assets: a major label that wasn’t at the time in the habit of dumping slumping acts, and a portfolio of songs that would prove eminently coverable in years to come. Holly had already gone to New York to cut “It Doesn’t Matter Anymore”; it doesn’t seem unreasonable to think that he might have ended up as a songwriter somewhere in the general vicinity of the Brill Building. (Then again, “It Doesn’t Matter Anymore” wasn’t one of his own; Paul Anka wrote it.)
J. P. Richardson, aka the Big Bopper, also had songwriting chops: he wrote “Running Bear” (Johnny Preston) and “White Lightning” (George Jones). “White Lightning” in particular gave him Nashville credibility; like many rock and roll acts — think Brenda Lee, Conway Twitty, or Wanda Jackson — he could have transitioned to country rather easily.
Ritchie Valens, I suspect, would have reclaimed the rest of his surname, which was “Valenzuela,” and become Carlos Santana before Carlos Santana ever did.
And Don McLean, bless him, would be better known for that lovely little song about Vincent van Gogh.
Alternate theories are welcomed.