In light of the new Buddy Holly tribute record with Paul McCartney and Lou Reed, this week Jason Hartley travels back in Advancement time to explore Buddy Holly’s lost potential as the greatest Advanced artist of all time.

A new Buddy Holly tribute album featuring Paul McCartney (“It’s So Easy”), Patti Smith (“Words of Love”) and Lou Reed (“Peggy Sue”) is coming out in June. The occasion is what would have been Buddy Holly’s 75th birthday. This got me to thinking about what might have been in Advancement…

Since Advancement didn’t exist—or at least it wasn’t recognized—until the early 1990s, it’s difficult to say if it would have been possible to tell in 1964 that Bob Dylan would one day be doing women’s underwear commercials and Marlon Brando would be appearing in video games. But now that we do have a sizable list of Advanced Geniuses from which to learn, we can look backward at their early careers to find clues for their future Advancement. These clues may make it possible to pick out current artists and others who may one day Advance. I can’t predict how the next generation will Advance, but I can at least identify those who have either achieved enough to qualify or at least show enough promise to think that one day they will qualify.

Unfortunately, many promising artists didn’t live long enough to achieve full Advancement. For instance, Kurt Cobain was conflicted in the way an Advanced Artist never is, wishing he could enjoy rock stardom like Freddy Mercury but still keep his status as a disaffected punk rocker. But I do think that if he had had the courage as an artist to go forward with what he truly believed in, he might still be with us today. He probably would have remained Overt, but I would take a living Kurt Cobain over a dead one any day, no matter how Overt.

Cobain is a member of the 27 Club (rockers who died at the age of 27), which also includes Brian Jones, Jim Morrison, Janis Joplin, and Jimi Hendrix. I don’t think Jones would have ever Advanced, but only because he was an under-the-radar kind of a guy. Morrison was one of the few artists of the late 1960s era to put Woodstock and the hippie movement in general in its proper perspective (it’s just kids having a good time and that’s always good). He certainly had the leather covered, and he sang the blues pretty well for a poet/Lizard King. But one question will always remain for me: If he was such a rebel, why did he show such a slavish devotion to rhymed couplets? Was he just a lazy writer or was this some early sign of Advancement?

I’d really like to think that Janis Joplin would have embraced Advancement. While her music was mostly blues-based rock’n’roll, there were other elements to it that she could have developed. She could have gone cabaret (like Bette Midler, who played a version of her in The Rose!) or country (like k.d. lang?). Perhaps it would have been Joplin who did her interpretation of the American songbook rather than Rod Stewart. Maybe she would have sung with Sting and Bryan Adams. Now that’s a world I would like to live in.

But of all the members of the 27 Club, Jimi Hendrix seems like the one most likely to Advance. All of his contemporaries report that seeing him for the first time was like looking into the future. Brain Eno refers to him as the first proper electronic musician. And while I don’t think Hendrix would have become as preppy as Eric Clapton, it would have been interesting to see what would have happened to him after he ditched the headbands and boas. Might he have given up on the guitar completely for the synthesizer? Would he have played on Paul McCartney solo records instead of Steve Miller? Might he have been in Cream or the Traveling Wilburys? Or would he have written a song for Rob Thomas instead of Carlos Santana? Whatever his path would have been, I feel confident that it would have been Advanced.

Buddy Holly didn’t live long enough to make it into the 27 Club, which is incredible (and unbearably sad), considering what he accomplished. Though he died at the age of 22, he is among the most influential rock musicians of all time. What is so tragic is that he had such Advanced plans for the future: He was going to learn flamenco guitar, collaborate with soul and gospel singers, and he had registered for classes at the Actor’s Studio where James Dean and Marlon Brando studied. The kicker is that he wore dark sunglasses during his wedding. One day I’d like to make a movie about an alternative universe where Buddy Holly decided not to do that last tour and became the most Advanced Artist of all time, more Advanced than Lou Reed, Marlon Brando, and Orson Welles put together. And of course the perfect person to play the role of the older, Super Advanced Holly would be Gary Busey. While I look for funding, I’ll just have to settle for listening to Lou Reed singing “Peggy Sue.”

For more on Advancement, check out Jason’s book The Advanced Genius Theory.