Of course, any answer to this question is purely speculative, but here are some things I think MAY have happened if that plane had safely arrived at its destination:

The Big Bopper was largely a novelty act, with one, maybe one and a half hits. Chantilly Lace and a version of White Lightning that predates the George Jones version many of us know. I find it unlikely that he would have had very much impact had he lived, but you never know.

Ritchie Valens may have grown into a bigger star than he he is, and possibly might have pushed racial boundaries in rock music toward a bit more Latin flavor. Oh, Donna was a rather pedestrian love song, but I gotta admit that he had a hot take on La Bamba. Had he lived and pursued more of that guitar driven sound with a Spanglish lyrical base, there may have been some interesting things to come out of that, and we may have had more (and earlier) successes from acts like Freddy Fender or an earlier instance of someone like a Carlos Santana. I think that could have been interesting, and I wonder what effect a longer career for Valens would have had on British kids devouring every rock and roll record they could get their hands on. What if the British Invasion had not just R&B to bounce back to the US, but also a Southwest blend of White and Brown culture?

Buddy Holley, though.. that’s the one that really intrigues me. Even with as short a career as he had, he was such a huge influence. When coming up with a name, The Beatles were referencing Buddy’s band The Crickets. The Stones covered Holley early on. Linda Ronstadt built her 70’s career on, among other things, Buddy Holley covers. Buddy was already breaking the perceived rules of Rock and Roll before he died. Unlike Elvis, Buddy had a hand in writing most of his recorded material. Buddy was already messing with the standard Verse/chorus/verse/chorus format of rock and roll songs, and working to gain the kind of individual control over his music that nobody was attempting at the time. Given time, I think Buddy Holey could have really pushed the boundaries of “Rock and Roll” and perhaps hastened the advent of “Rock” music by quite a bit. A longer and successful career for Holley may have brought forth a singer-songwriter movement far sooner that such a thing happened. Like I said, it’s all purely speculative, but I really think Holley had more potential to change the industry than any other early rocker.

On the downside, without that plane crash, I suspect Waylon Jennings would have continued in Holley’s band for a career had that plane crash not happened. There would have been no Waylon Jennings solo career, and all the influence that has had on the genre now known as “Alt-Country,” “Outlaw Country,” or “Americana” would probably be different, if it had happened at all.

Still… I find it fascinating to wonder what Holley would have done with decades to play….