When Rolling Stone Senior Editor David Fricke published a list of The 100 Greatest Guitarists of All Time, some readers might have been surprised to see someone called Zoot Horn Rollo outranking Eddie Van Halen, Johnny Winter, and Mick Ronson — not to mention pioneers like Lightnin’ Hopkins and Link Wray, bona fide rock stars like Neil Young, “player’s players” like the white-hot Danny Gatton, and dozens more. Zoot ... um, huh? What did one of America’s most respected rock critics know that legions of music fans didn’t?

He knew that in 1968 an intellectually curious teenage guitar player in the L.A. avant-garde had joined up with Don Van Vliet, a.k.a. Capt. Beefheart, to record one of the most outrageous and eclectic albums of all time. It was released in June, 1969. Zoot was 20 years old. With a name like Trout Mask Replica and a cover photo at once comical and nightmarish, the record fairly screamed “We’re not normal” before its vinyl was gouged by needles. It was too weird for mass consumption, and it failed to chart. And yet a quarter-century later, when Rolling Stone published its list of The 500 Greatest Albums of All Time, Trout Mask outranked 440 of them.

The sonic mayhem of the Beefheart collaboration took its toll not only on the ears and psyches of listeners unprepared to have their heads unscrewed and handed to them but also on the sensibilities of the band members. ZHR stuck it out with the difficult Van Vliet until ’74, when he walked away, reclaimed his real name — Bill Harkleroad — and set about figuring out the rest of his life.

I mentioned to a group of aspiring music journalists one time that the first thing we heard about Bob Dylan was that there was some guy on the radio who couldn’t sing. People hadn’t begun to feel the impact of his art; all they knew was, he wasn’t the sort of pop crooner they were used to. His earliest work was so challenging that it took a while to take hold. About 30 minutes after my comment a young woman raised her hand and said, “It occurs to me that every record that ever meant anything to me was challenging at first and took some getting used to.” I thought it was an important insight. Breaking ground is inherently disruptive. Subversion takes guts.

For guitar players and other listeners who grew up on what Michael Bloomfield called the “simple sonorities” of folk, rock and roll and even surf music, it came as a surprise to learn that the Beefheart alchemist behind all of that so-called psychedelic-era guitar wackiness was enamored of those same musics. When Bloomfield walked away from the rock star life, he cited the rootsy eclecticism of Ry Cooder as an inspiration. “I thought, here is a man who had his eye on a certain sparrow,” he told me, “making record after record and constantly refining his diamond ….”

The music Bill Harkleroad has created in recent years somehow evokes the earthiness and passion that made rock and roll so sensual in, say, 1956, and made surf music so irresistibly catchy in 1963, and turned 3-chord country standards into some of the most heartbreaking poetry ever to seep out of a roadhouse jukebox. His music would never be mistaken for vintage rock or surf or country, but it shares a soul connection with those styles, even while, like the music of Jimi Hendrix, it takes us not only to new places but to places we didn’t even know existed.

Combining pelvic-tilting raw energy with stratospheric improvisation sounds impossible, but that’s what virtuosos do. They make it look easy. How does he do it? Who’s to say? Maybe even Bill himself couldn’t explain it. He teaches guitar and has a unique and effective take on learning the instrument (I once told him the money I paid for my first lesson was the best 35 bucks I ever spent; whatever he charges these days is worth it). But when it comes to his own music, explaining what he does isn’t his job. His job is to make art, and he does, and like the music of Beefheart and Dylan and Hendrix, it’s new and inspiring.

Bill Harkleroad has covered a lot of ground since listeners were challenged, intrigued and provoked by Zoot Horn Rollo and his fellow revolutionaries, but the teenager’s passion and the restless creativity have never left him. He continues to chart his own course, his music heartfelt with a twist, his eye on a certain sparrow, refining his diamond.