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Join the room"A Bad Goodbye" is a song written by American country music artist Clint Black, and recorded by him as a duet with fellow country music artist Wynonna Judd. The song was recorded after the two toured together during their "Black and Wy" tour in 1993. It was released in May 1993 as the first single from Black's album No Time to Kill. It peaked at number 2 on the Billboard Hot Country Singles & Tracks chart, behind "Chattahoochee" by Alan Jackson. In addition, it was Black's first appearance on the Billboard Hot 100, peaking at number 43 there.