In 25 years, Wynn has released at least that many albums and has seen over 300 of his songs recorded. He has played over 2000 shows in more than 25 countries. His songs have been recorded and/or performed by REM, Luna, Concrete Blonde, The Black Crowes, Yo La Tengo and Eleventh Dream Day, among others; his "That's Why I Wear Black" became the #1 single of 1993 in Norway as the leadoff track from the debut album by Somebody's Darling. He has been prominently featured in Rolling Stone, Mojo, Uncut, Entertainment Weekly, People, The Los Angeles Times, New York Times and countless other publications all over the world.