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Among early rock and rollers, Buddy Holly was an anomaly.

Tall, bespectacled, with a gawkiness he never lived to outgrow, he was no Elvis Presley, at least in terms of dangerous sex appeal. But Holly was a true rock and roll star, the first cool geek, opening the door for generations of glasses-wearing rockers like John Lennon, Roy Orbison, Elton John, Elvis Costello and Rivers Cuomo.

He was also a trailblazing innovator whose remarkably short career—he spent just 18 months at the top—left a legacy that endures to this day.

While Elvis and other stars of the era had their hits penned by professional tunesmiths, Holly wrote his own material. With his band the Crickets, he pioneered the two guitar, bass, drums and vocals format for rock bands that would be adopted by the British beat groups and is still in use today.

He was also the first high-profile rock and roller to adopt the Fender Stratocaster as his guitar of choice.

Holly got his first Strat in 1955, at Adair Music in his hometown of Lubbock, TX after his older brother Larry loaned him the money. At the time, Strats were more popular with country musicians; which may have been part of what attracted Holly to the guitar, as his fingerpicking and twangy lead style owed a debt to his country-and-western musical roots.

With his band the Crickets, Holly pioneered a distinct guitar style that deftly merged rhythm with lead, and at times, seemed to parrot his hiccupping vocals.

He used techniques like sweep picking—using a downward pick stroke to push through three strings and an upstroke for the fourth note—and would muffle his strings or toggle his pickups to create the exciting dynamics that made his records leap out of the speakers.

If there was one thing that really distinguished Holly’s playing, it was his unconventional strumming technique. He used down strokes exclusively, keeping his wrist locked to achieve the furious, driving rhythm heard on early Crickets recordings. While he was a capable soloist, he often spurned the incendiary lead style deployed by the likes of Chuck Berry in favor of rhythmic, chord-based solos like the one on “Peggy Sue.”

With his Stratocaster plugged into Magnatone Custom 280 and later a Fender Bassman, Holly’s guitar sound was stripped down and simple. But it was louder than most at the time, with the Strat’s full sound lending itself to the chunky rhythms that drove Holly’s recordings.

Along with his thick-framed black glasses, the Stratocaster was also an enormous component of Holly’s image, particularly in England, where few (if any) Fender Strats had been seen before.

As Frank Allen, guitarist of the Searchers told the Independent, “While we were skiffling away trying to find a fourth chord, Buddy was giving us the opening bars of ‘That’ll Be the Day,’ with unbelievable expertise and on an instrument that was the equivalent of a bullet-finned ’59 Cadillac. He looked gangly and geekish with those glasses but that guitar made him unbelievably cool.”

While he was a major star at home, Holly resonated with English audiences in a way few of his contemporaries, perhaps not even Elvis, managed to do. It’s telling that the Beatles adopted their moniker because they wanted an insect name like the Crickets, and that the Stones’ first top 10 hit was a cover of Holly’s “Not Fade Away.”

“Listen to the songs on the first three Beatles albums,” said John Mellencamp to Rolling Stone. “Take their voices off and it’s Buddy Holly.”

Holly’s untimely death in the plane crash that also claimed the lives of Ritchie Valens and the Big Bopper—known colloquially as "The Day the Music Died"— was a tragedy on a great many levels. Mainly the loss to his wife, Maria Elena Santiago, who was so stricken she couldn’t attend her husband’s funeral.

But putting personal tragedy aside, it’s tantalizing to imagine what Buddy Holly might have achieved had he survived into the ‘60s. Rock and roll’s first real singer/songwriter/guitarist, Holly was living in Greenwich Village at the time of his death, exploring recording techniques and had spoken to his wife about opening a studio in London.

Holly was always an unlikely figure for a ‘50s rock star. But the ‘60s would seemingly have suited him. His guitar chops, songwriting ability and curiosity about the recording process suggest he would’ve weathered the turn of the decade better than many his early rock and roll contemporaries did. He would also have looked cool with Dylan hair and Lennon specs.

Although his career was short, as the first major artist to play a Fender Strat, Holly had a massive influence on future guitar gods like George Harrison, Eric Clapton and Jeff Beck. Even today, the Texas rocker’s influence persists and is unlikely to fade away any time soon.

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