Songfacts®:

• In this song, the Philadelphia singer Kurt Vile looks in the mirror and doesn't recognize the man he sees, although he thinks the clothes he's wearing are "pretty pimpin."
  
  When you're startled by the man in the mirror, it's usually a pretty bad sign and often an effective wake-up call. In many cases, addiction or insanity is the problem, but it seems Vile just needs some rest. "I was just mentally exhausted," he told Rolling Stone. "I think most people feel like that at times."
  
  Vile says that the song is based on a true story.
• Daniel Henry directed the video, which finds multiple images of Vile sharing the screen, representing the different likenesses he imagines. Other videos by Henry include "High Ball Stepper" by Jack White and "The Garden" by Yumi And The System.
• "Pretty Pimpin" is Kurt Vile's best-known song. Unless you were a music critic or had eclectic taste, you probably hadn't heard of him when the song emerged. Vile did time in the band The War on Drugs before putting out his first solo album in 2008. His 2011 album Smoke Ring For My Halo got the attention of publications like Pitchfork, which put it on their list of the Top 20 albums of that year. "Pretty Pimpin" comes from his 2015 album B'lieve I'm Goin Down.... The song became Kurt Vile's first to make a chart impact: it went to #1 on Billboard's Adult Alternative Songs tally in March 2016.