Songfacts®:

• In this song, John Mellencamp has already shelled out $53 on a date, and he thinks it's going nowhere. But then he gets a very pleasant surprise. She leans over and whispers in his ear, "Get a leg up, boy," a welcome invitation. His night keeps getting better when she invites a friend over, making him "Lucky Pierre" indeed.
• Many of Mellencamp's singles in the late '80s had a significant message behind them - "Jackie Brown" (poverty) and "Pop Singer" (navigating the music industry) among them. But he entered the '90s with "Get A Leg Up," a lively rocker that deals with the pleasures of the flesh. It's not an unfamiliar topic in his songs, as a listen to his early hit "Hurts So Good" will show.
• The line, "You know I ain't that handsome, but you know I ain't shy, shy, shy" is a nod to Bob Seger's "Ramblin' Gamblin' Man," a formative song in Mellencamp's musical upbringing. In that one, Seger sings, "I ain't good looking, but you know I ain't shy."
• Mellencamp's love interest in the video is the supermodel Elaine Irwin, who became his third wife the following year. They met on the set of the video, which doubled as the album cover photo shoot.
  
  Irwin and Mellencamp had two children before splitting up in 2010.
• The video was directed by Jonathan Kaplan, who also directed the 1988 Jodie Foster movie The Accused and Mellencamp's "Rain On The Scarecrow" video.
  
  The paintings in the video are Mellencamp originals; he considered becoming a painter before making music his full-time job. Many of the paintings he made after taking some time off following the release of his Big Daddy album in 1989.
• "Get A Leg Up" was the first single from the Whenever We Wanted album. It went to #1 on Billboard's Album Rock Tracks chart and helped the album sell over a million copies, just as all his '80s albums had.