"Goodbye Little Boy" was the first single released in March 1989 by Australian folk rock group The Triffids ahead of their album The Black Swan. Lead vocals are provided by Jill Birt, their keyboardist, instead of David McComb, the group's usual lead singer. Birt is also featured on the single's front cover.
"Goodbye Little Boy" was produced by Stephen Street (The Smiths, Morrissey), and was co-written by McComb and Adam Peters. The B-Side "Go Home Eddie" was written by McComb and produced by Street. The songs were recorded between September and October 1988 at The Justice Room, Cathanger, Somerset. "Shell of the Man" was written and produced by McComb. The single was released as a 7", 10", 12" and CD single versions.
"Goodbye Little Boy" reached No. 81 on the Australian Kent Music Report Singles Chart in April 1989.