Songfacts®:

• An intermezzo is a piece of music that connects two movements in an opera. This song takes place in Key West, Florida, at the Hotel Flamingo, where Mellencamp is hanging out with a guy named Gypsy Scotty. It's a story song, with Scotty winning the affections of a beautiful woman Mellencamp covets. "I saw you first," he tells her, as if that gives him claim.
  
  By calling the song an intermezzo, Mellencamp implies transition, as if this stopover in Key West leads to a bigger life story.
• Mellencamp wrote this song with George Green, his longtime friend who often worked on songs with him, including "Hurts So Good" and "Crumblin' Down."
• "Key West Intermezzo" was the first single from Mr. Happy Go Lucky, an album titled as a joke because Mellencamp had a reputation for being a bit surly. It came after two major life events: his marriage to Elaine Irwin in 1992, and his heart attack in 1994.
  
  The song got a lot of airplay on pop, rock, and adult contemporary radio, but it was his last Top 40 hit. As Mellencamp got older, he kept making music but found it harder and harder to get on the radio.