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Creaky Boards’ 2008 sophomore release Brooklyn Is Love wasn’t marketed as a concept album, but its songs center heavily on two themes from songwriter Andrew Hoepfner’s life: his relationships with women and his relationship with his own art. Opener “The Songs I Didn’t Write” (yes, the one with the silly YouTube video about Coldplay) concerns both, narrating an internal struggle between the great musician Hoepfner wants to be and the caring partner his beloved deserves. By the time Track 2 rolls around, the artist has won and the girl is gone, leaving Hoepfner to confront his own demons of doubt and regret. And yet, “Now I’m in the City” is amongst the album’s brightest, bounciest numbers, full of rousing choruses, pogo-worthy breaks, and wide-eyed enthusiasm for what’s to come. When you think you might have just made the biggest mistake of your life, a sunny outlook goes a long way.

Jeffrey Lewis, “Williamsburg Will Oldham Horror”
(City & Eastern Songs, 2005)

Hoepfner shares a peculiar gift with Jeffrey Lewis: both frequently focus on their own insecurities and fears, and yet both do so with striking confidence and eloquence. This paradox pops up in about half of Lewis’s songs, but “Williamsburg Will Oldham Horror” is  perhaps the most perfectly realized example. It’s his own “Like a Rolling Stone” in a way, looping the same three notes over the same three chords for six minutes, and yet keeping listeners on the edge of their seats with a spiraling stream-of-consciousness monologue on the bemusing nature of success.