It is no exaggeration to call Little Walter the Jimi Hendrix of the electric harp: he redefined what the instrument was and what it could do, pushing the instrument so far into the future that his music still sounds modern decades after it was recorded. Little Walter wasn't the first musician to amplify the harmonica but he arguably was the first to make the harp sound electric, twisting twitching, vibrant runs out of his instrument; nearly stealing the show from Muddy Waters on his earliest Chess recordings; and so impressing Leonard Chess that he made Muddy keep Walter as his harpist even after Waters broke up his band. Chess also made Walter into his studio's house harpist and started to release Little Walter solo records with the instrumental "Juke" in 1952. "Juke" became a smash hit and turned Little Walter into a star, making him a steady presence on the '50s R&B charts.
Road Runner, the second volume of Hip-O Select's ongoing chronicle of Bo Diddley's complete Chess/Checker master recordings, covers roughly one calendar year whereas its predecessor, I'm a Man, spanned four — a good indication that 1959 was an eventful year for Bo. During this one year, he had his biggest pop hit in the jive-talking "Say Man" and had another sizable R&B hit with "Crackin' Up," but both these sides were cut in 1958 and released as a single in 1959.