And after that, believe it or not, I FINALLY agree with Scott Colvin about the genius of "Why Can't I?" However, he already talked about that song. And it still isn't my favorite of hers.
My favorite Liz Phair song remains to this day to be song #17 on her landmark Exile in Guyville album. Some have described this song, her second single, to be some of the greatest words ever put together, and I cannot disagree with that. The analogies between life and a movie throughout the song are creative and somewhat uplifting. Plus, any reference to the great Galaxie 500 is an added bonus.
It might sound strange, but I think my SECOND favorite Liz Phair song is also "Stratford-on-Guy". As some of you may know, she got her start by self-recording a few cassettes marketed as Girlysounds. Many of the Girlysounds songs ended up being rewritten and used on her first three albums, mostly with revised lyrics.
In many interviews, it has been implied that Exile in Guyville was a call-and-answer response to each track on The Rolling Stones' Exile on Main Street. This would make "Stratford-on-Guy" a response to "Shine a Light" (and I will happily go track by track through both at some point to prove that it's a decent concept). She didn't sit down and write songs expressly for this purpose. She used material she already had and lifted the Jagger/Richards album structure, because she didn't know how to construct an album.
Luckily, she rewrote this song a bit to fit the theme. In its Girlysound version (actually titled "Bomb"), it's a much darker song. And ends with a plane crash. It still maintains the excellent analogies, though.