The song begins at a slow pace accompanied by piano, with the narrator explaining that he has no fear of dying, but that he wants to go on being himself after he has died. After the introduction, the tempo increases and the narrator elaborates on his initial point, by stating that he wishes to have his body placed against a jukebox should he die, so that he will still be in a familiar atmosphere after death. The radio edit omits one repetition of the chorus.
In 1999, the song was part of a lawsuit when another songwriter named Everett Ellis attempted to sue the writers of "Prop Me Up Beside the Jukebox", as he thought that the song infringed on a copyright to his own composition, "Lay Me Out by the Jukebox When I Die".
The music video for the song begins with two men smuggling a fully dressed male corpse out of a funeral home. They proceed to take it out for a night on the town. The night of fun ends with the now-abandoned corpse (wearing sunglasses and a party hat) propped up next to the jukebox. Diffie (who plays the song at the bar) walks up to the corpse afterwards, thinking it's a living person, and tells him that, since the bar is closing, he needs to leave... adding "you don't have to go home, but you can't stay here". Diffie then claps the corpse on his shoulder and leaves. The corpse begins to sway and collapses next to the jukebox.