20. Buddy Holly
Band: The Crickets; Buddy Holly
The guy made thick framed glasses cool. Every nerd who lived after Buddy Holly pioneered both rock 'n roll and rockstardom needs to thank the ghost of the man who saved them from countless wedgies. Touted as the greatest influence on classic and modern rock, he was also definitely a style influence on the musicians who came after his late '50s success. His death was known as the day the music died, but luckily his style legacy carried on.