[3] "Cherry Bomb" is a nostalgic song that reflects on Mellencamp's teenage years hanging out at the Last Exit Teen Club.

[4][5] The single was released in the United States in October 1987, backed with the B-side "Shama Lama Ding Dong".

The music video for the song features a couple dancing intimately with one another near a jukebox while Mellencamp dances by himself, switching to Mellencamp and his band playing the song on a beach, interspersed with vintage video clips.

"Cherry Bomb" features a female voice (Mellencamp background singer Crystal Taliefero) and two other male voices (band members Toby Myers and Mike Wanchic) in addition to Mellencamp's on the second verse.

Mellencamp told GQ magazine in 2022 what inspired him to have voices other than his own take turns singing lead: "Sly and the Family Stone.