283. Steve Earle
The trend of artists on this list who struggles to find airplay on radio continues with Steve Earle. With the main exception of Copperhead Road, Earle’s music was too Country for Rock stations, and the songs that sounded Country enough were laden with leftist politics which generally does not fit the traditional Country audience. At his core, he is a basic American Roots Rocker who although the parallels that he gets to Bruce Springsteen are not completely unjustified, he may always struggle to find one tenth of Bruce’s audience.