Rick Springfield manager Joe Gottfried made a deal with producer Keith Olsen: If Olsen produced two of Springfield's songs, Gottfried would build him a studio. Once the deal was made, Springfield — who had turned to acting in soap operas as his musical career faltered — gave Olsen several demos, and one song stood out. "I never really thought of it as a single," said Springfield. "I thought there were better songs on the album, actually." Though the song is about a guy who falls for his best friend's woman, in real life, "Jessie" was a fellow art class student Springfield didn't know that well.