"Setting Me Up" is a song written by Mark Knopfler. It was originally recorded by British rock group Dire Straits on their self-titled debut album but not released as a single. Ken Tucker in Rolling Stone described the song as a "heavenly number" combining humor with bitterness, despite having a typical messed-up romance theme. Tucker noted that the song's impact is enhanced by the growling tone in Knofler's singing voice and by the song's country music-style guitar solo. Carly Darling in Billboard Magazine praised the song's rockabilly guitar but criticizes the lyrics.
"Setting Me Up" is one of five songs that Knopfler's publisher made country demos of without the songwriter's approval, leading to a number of country covers of this and other songs. American country music group Highway 101 covered the song for their 1988 album Highway 101² and released it as the album's third single in January 1989. The song reached #7 on the BillboardHot Country Singles chart in April 1989.