Asked by American Songwriter magazine in 2015 if there is a song of his that he is most most proud of, Colin Melroy replied naming this track from The Decemberist's second record. He explained: "It's kind of a statement to the world. I think it worked well."
"It was such a funny song to play live when we were playing little clubs," Melroy continued. "There was an irony to it that now is almost completely lost. Once you start playing big theaters, the tragedy of it flips and suddenly it loses some of its shimmer. I still love that song a lot, but I loved it most in 2004 or 2005."
"Piano Man" was inspired by Billy Joel's time playing at a piano bar in Los Angeles. The "real estate novelist" was a guy who always talked about writing a book, but spent all his spare time in the bar.