Not A Pretty Girl is the sixth studio album released by singer-songwriter Ani DiFranco on her own record label, Righteous Babe Records. Cited by many fans as her finest work, the 1995 album extended the punk-edged folksinger's early formula of acoustic guitar and drums to a passionate crescendo. On subsequent records, DiFranco would add electric guitar, horns, band members and guest musicians, but on Not A Pretty Girl she belts out her guitar licks and her political-yet-personal lyrics accompanied most often by Andy Stochansky's fitful and emotional percussion alone.

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 brief yet powerful spoken-word track "Tiptoe", 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.

The track "Shy" earned DiFranco a 1997 Grammy Award nomination for Rock Folk Vocalist.