Rufus Wainwright - "The Art Teacher" (2004)
Originally released as part of a four song EP Between Wainwright's Want One and Want Two entitled Waiting for a Want.
Really interesting song. It's a man singing as a woman telling a story about her days as a high school girl. It doesn't have a chorus, or even verses really, just a stream of conscious story. The vamping on the piano before he starts a line actually makes it sound like he is sitting in a parlor, telling you this story, deciding if he wants to tell you the next part. He breathes in a long drag of a cigarette connected to a long elegant cigarette holder; then takes a sip of the pinot grigio, before finally finishing the thought. I found very few liner notes about the album, but I did find a uncited source claiming that the song was recorded live for the album. Every version I found online that says it was the album version had the people cheering at the end, but that doesn't prove it, just makes it more likely. The book agrees, but there's no documentation I found.
The song is one of the simplest forms of music: a story told by one person, with one backing instrument. The only break to this is the horn that comes in at the middle of the piece. Performed by Isobel Griffiths, the same source that claims it was recorded live (in Montreal) also claims that the horn was added later in the studio. It's a tragic sad story, told beautifully.