According to Aimee Mann in a 1985 interview with music video station V66, director D.J. Webster obtained the establishing shot of Carnegie Hall "illegally".
The song's lyrics, written by the band's front-woman Aimee Mann, portray a lover in an affair, and were originally written and sung as if to a woman, but changed due to Epic Records' pressure.
The song was inspired by Mann's breakup with 'Til Tuesday drummer, Michael Hausman.
The accompanying music video, directed by D.J. Webster, received wide exposure on MTV, positive reactions from critics, was nominated for numerous awards, and is thought to be the reason behind the song's success.
The song was released in North America in March 1985.