Songfacts®:

• This song is about a twisted crazy love affair, as evidenced by the lyrics, "I loved her, she loved me, we shared a needle a couple of times" and "I warn you, if cornered, I'll scratch my way out of the pen." >>

  Suggestion credit:
  John - Los Angeles, CA
• "What Jail Is Like" is a haunting and deeply introspective exploration of guilt, redemption, and the search for meaning in life. Greg Dulli's lyrics use vivid and often disturbing imagery to paint a picture of his struggles to come to terms with his own moral failings and the consequences of his actions.
• This was the first song Dulli wrote for Gentleman. He penned it overseas while touring the Afghan Whigs' 1990 album Up in It.
  
  "I don't remember the circumstances, but I remember I had become frustrated trying to make a phone call to the United States and not getting through and I was highly agitated," Dulli recalled to Spin magazine. "When you're sad or angry or things aren't going well in your life, and in your mind you're looking for blame placement and shooting all the rounds at everybody else - that's a slippery moment. That song is blaming other people for my problems, and I had yet to examine my own culpability, and full-stop examined it on that one."