Songfacts®:

• There is no official soundtrack to the Judd Apatow movie Knocked Up, which Loudon provided a number of songs for, but Strange Weirdos is described as "Music from and inspired by the film Knocked Up" and there's a live version of this song featured as an "Extra" on the DVD to the movie. Loudon appeared in the movie as Dr. Howard.
• This song describes a long-lasting relationship where the singer freely admits that he was not always comfortable with the idea of being in love, but his partner knows him better than he thinks: "The stain of love's a smudge upon my brow, but you see through me." >>>

  Suggestion credit:
  Robert Campion - Galway, Ireland, for above 2
• "You Can't Fail Me Know" was co-written and co-produced by Joe Henry (an acclaimed singer/producer who wrote "Don't Tell Me") and is featured on his album Civilians. NPR music reviewer Allison L. Stewart compares Henry's version to Loudon Wainwright's: "Formerly a slow, hookless strings-and-guitar ballad, it's now more sparse, more morose (assuming that's possible) and even lovelier."
  
  Henry probably wouldn't agree, considering he is a huge Loudon Wainwright fan; he even calls the singer a hero and a mentor. After the two worked together on "You Can't Fail Me Now" and several other songs for the Knocked Up soundtrack, Henry could barely keep from gushing about the singer in an LAist interview: "No he's not just a regular guy. I mean he's a good friend, but I don't hold him in any less high esteem. I think he is one of the most underrated songwriters considering his influence."