On subsequent records, DiFranco would add electric guitar, horns, band members and guest musicians, but on Not a Pretty Girl she was accompanied by Andy Stochansky's percussion alone.

According to AllMusic, "Light of Some Kind" is a "deeply felt portrait...in which the singer seems to be confessing to a man that she has been unfaithful to him with a woman".

[1] Released on Living in Clip, the track "Shy" earned DiFranco a 1997 Grammy Award nomination for Best Female Rock Vocal Performance.

[6] "Shy" off the album is notable for being quoted by Matt Skiba of Alkaline Trio during live performances of the song "Ninety-Seven".

[citation needed] The CD 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.