"Blue Side of Town" is a song written by Paul Kennerley and Hank DeVito, and recorded by American country music artist Patty Loveless. It was released in October 1988 as the first single from her album Honky Tonk Angel. Loveless purchased the recording rights to this song in 1985, a few years before she recorded it but it was not included on her self-titled album, Patty Loveless. The song charted for 22 weeks (her longest to date) on the Billboard Hot Country Singles and Tracks chart, reaching #4 during the week of January 14, 1989.