Songfacts®:

• "The Man Who Couldn't Cry" begins like a twisted nursery rhyme which, of course, is the best kind:
  
  There once was a man who just couldn't cry
  He hadn't cried for years and years
  Napalmed babies and the movie Love Story
  For instance could not produce tears.
  
  The movie Love Story (1970) was a maudlin tearjerker starring Ryan O'Neal as a wealthy college student in love with the cancer-stricken Ali MacGraw. Napalmed babies (a reference to the Vietnam War) are one thing, but can't cry at Love Story? Unthinkable!
• Wainwright spoke of the song's genesis, and legacy, in an interview with the A.V. Club: "That's a kind of strange, long, allegorical song. I just kind of made that one up about somebody, although the idea of not being able to cry is an interesting one, particularly for men. The exciting thing about that one is that Johnny Cash recorded it, which was a huge thrill, to have somebody of his stature think it was good enough to record. I always think of that when I think of that song."
  
  Cash recorded the song during a live performance at the Viper Room nightclub in Los Angeles. It was released on his 1994 American Recordings album.