How Much It Hurts

Warren wanted a Beach Boys thing for this one, and Carl Wilson and Billy Hinsche came in, with Carl arranging the vocal parts. The other harmony vocalists (credited as the "Gentlemen Boys") were Jackson Browne, J.D. Souther, Zevon's longtime backers Waddy Wachtel and Jorge Calderon, and Linda Rondstadt/Stone Poneys guitarist Kenny Edwards.

He certainly did earn that reputation.

Like a lot of the other comments are saying, I think this mainly about voyeurism. If the song was about his girlfriend, then why would he use the word spy. If you are a spy it means you shouldn't be caught, that is kind of the whole point, and if you are a voyeur, the whole point of the pleasure you get from it, is the fact that the other people don't know you are watching them. See a bit of a connection there?

This song is def a twin to "Unfair" (a song she has been quoted as saying is about falling in love with someone who is already in a relationship) so it is presumably about the same person. Given the references to buying an apartment and not being able to see her love interest "after tonight," it's most likely that she's moving away and she'll "wait a day to break the bad news" (i.e. notifying him that she's leaving once she's already gone). And, of course, the fact that she sees in him a fellow "idealist" and "dreamer" (terms commonly given to people with the INFP personality on the Myers–Briggs Type Indicator (MBTI)) portends that she'll always be left wondering if they would've been perfect together.

This is a hauntingly beautiful song about introspection, specifically about looking back at a relationship that started bad and ended so poorly, that the narrator wants to go back to the very beginning and tell himself to not even travel down that road. I believe that the relationship started poorly because of the lines: "Take me back to the night we met:When the night was full of terrors: And your eyes were filled with tears: When you had not touched me yet" So, the first night was not a great start, but the narrator pursued the relationship and eventually both overcame the rough start to fall in love with each other: "I had all and then most of you" Like many relationships that turn sour, it was not a quick decline, but a gradual one where the narrator and their partner fall out of love and gradually grow apart "Some and now none of you" Losing someone who was once everything in your world, who you could confide in, tell your secrets to, share all the most intimate parts of your life, to being strangers with that person is probably one of the most painful experiences a person can go through. So Painful, the narrator wants to go back in time and tell himself to not even pursue the relationship. This was the perfect song for "13 Reasons Why"