Facts and Bob Dylan have always made for strange companions. As a teenager, Bob Dylan claimed that playing with Little Richard was his life goal—though he might have been joking. In 1960, before either Bob Dylan or the Smothers Brothers were well-known entities, the two acts performed together at a Denver club. A Columbia executive gave Bob Dylan a record deal … even though he didn’t have the authority to give Bob Dylan a record deal. Artist Suze Rotolo dated Dylan’s from 1961 to 1964, and she’s the woman pictured with Dylan on the cover of The Freewheelin’ Bob Dylan.