There are many signature DiFranco moments on this album: the title track's solemn chords and feminist message; the unapologetic physical cravings of "Shy" and "Light of Some Kind"; the lambasting of the music industry on "The Million You Never Made"; the joyous tranquility of "32 Flavors"; and the political activism of "Crime for Crime" and "Coming Up."
Not A Pretty Girl stands as a watershed album for DiFranco. It also intensified the word-of-mouth buzz and the occasional nod from alternative media, which are the predominant modes of publicity for DiFranco, who shuns the corporate music industry and as a result gets little airplay on commercial radio.
As a small rebellion in CD design, the case of Not A Pretty Girl is designed to be looked at 'the wrong way round', with the spine on the right hand side rather than the left.