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For one thing, his (somewhat) nerdy apperance was a revelation to legions of gawky teenagers with dreams of their own: here was a rocker who didn't look like Elvis. And he was rocking out in a completely unselfconscious way. It's a look that inspired countless geek rockers, from Elvis Costello to Rivers Cuomo, and yet it was utterly uncalculated. He also pioneered the idea of an artist with complete creative control, fighting for the right to produce his own records and write his own songs. The Crickets were rock and roll's first self-contained band, and that's Buddy's real legacy.
The music that band made is equally legendary, of course - a truly innocent and open-hearted (yet not naive) sound that was much more country-oriented than his peers (another nail in the coffin for the myth that rock was just white blues). It also employed non-rock instrumentation and production elements, further ensuring Buddy's status as a true innovator. Buddy released just about forty songs in 18 months before the infamous plane crash that took his life in 1959; the fact that his legacy and fame are the rival of folks like Elvis and Chuck Berry only proves just how powerful those songs were. And are.