Album: Ani DiFranco (1990); Not So Soft (1991)
Description: DiFranco's unorthodox, Muppet-with-a-conscience vocal contortions and lyrics address everything from abortion to the evils of corporations to the softness of a lover's body.
Sample Lyric: "Oh, no don't close your eyes/ I am writing/Graffiti on your body/I am drawing the story of/How hard we tried."
Typical Fan: Radical teenage feminists who shave their heads, stomp around in combat boots, and bemoan the stifling nature of their middle-class suburban existence.
Album: Imperfectly (1992)
Description: Most notable for its endless uncertainties: DiFranco's conflict between her perceived tough-girl persona and actual inner marshmallow ("I'm No Heroine"); why some women settle for jerks ("Fixing Her Hair"); and the pain of not fitting into a Susie Homemaker niche ("In or Out").
Sample Lyric: "I've got no criteria for sex or race/I just want to hear your voice/I just want to see your face."
Typical Fan: Bisexual-until-graduation hippie chicks who refuse to shave their armpits and refer to themselves as "womyn" or "hir" in drum circles and campfire sing-alongs.
Album: Puddle Dive (1993)
Description: A road-obsessed album that sounds as tossed-off as its stopgap, Livejournal-level "poetry."
Sample Lyric: "How come I can pick my ears/But not my nose/Who made up that rule anyway?"
Typical Fan: Disillusioned twentysomethings who disavow cubicle jobs in favor of following jam bands around and living off the earth's natural resources.
Album: Out of Range (1994)
Description: Occasional horn and accordion bursts break up the monotony of this uneven, little-considered disc.
Sample Lyrics: "You are a china shop/And I am a bull/You are really good food/And I am full."
Typical Fan: Those who purchased the album in 1994 and have it collecting dust on their record shelves next to discs by Arrested Development and Hootie & the Blowfish.
Album: Not a Pretty Girl (1995)
Description: Head-bobbing acoustic strums that allow DiFranco's best, most soul-searching words to rise to the fore.
Sample Lyric: "And God help you if you are an ugly girl/'Course too pretty is also your doom/'Cause everyone harbors a secret hatred/For the prettiest girl in the room."
Typical Fan: Ugly ducklings who need external reassurance that it's what's beneath their subpar mugs that really counts.
Album: Dilate (1996)
Description: A cathartic album detailing the recovery process from a breakup made all the more poignant by DiFranco's evocative, rocker-chick-styled guitar picking.
Sample Lyric: "I found religion in the greeting card aisle/Now I know Hallmark was right."
Typical Fan: Buttoned-up types who find DiFranco safe to listen to now that she's also writing about sleeping with men.
Album: Little Plastic Castle (1998)
Description: The last essential DiFranco disc, Castle throws urgent bits of orchestration over her sparest soul-baring moments.
Sample Lyric: "They say goldfish have no memory/I guess their lives are much like mine."
Typical Fan: Grunge ex-pats who caught the Lilith Fair bug.
Album: Up Up Up Up Up Up (1999)
Description: The bluesy dark sheep in her oeuvre. Here, she tones down past self-absorption in favor of intriguing character sketches and political diatribes.
Sample Lyric: "Up up up up up up/Points the spire of the steeple/But God's work isn't done by God/It's done by people."
Typical Fan: Newbie Ani obsessives who wore out their copies of Little Plastic Castle.
Album: To the Teeth (1999); Reveling: Reckoning (2001)
Description: Teeth is an ambitious album liberated by flutes, pedal steel, and saxophones. The genre-skipping, double-disc R:R, in contrast, feels like the overindulgent senior thesis of a brown-nosing music student.
Sample Lyric: "The sand is grey/And the ocean is grey/And I feel right at home/In this stunning monochrome."
Typical Fan: Starbucks-swilling professionals who want to embrace nonthreatening multiculturalism alongside their chai lattés and pressed khakis.
Album: Evolve (2003)
Description: Mellow and languid, Evolve delves into smooth jazz and funk-folk suitable for quiet winter nights at home in front of a roaring fire.
Sample Lyric: "'Cause when I look at you I squint/You are that beautiful/And my pussy is a tractor/And this is a tractor pull."
Typical Fan: Diehard granola lesbians who buy Ani records out of sheer habit and blind loyalty.
Album: Educated Guess (2004); Knuckle Down (2005)
Description: Basically higher fidelity versions of her earlier acoustic work. Guess earns demerits for pretentious spoken-word introductions.
Sample Lyric: "You're my seeing eye dog and I am blind/You take me there every time/With that winning combination of loyal and kind."
Typical Fan: Lapsed fans combing used-record stores for bargains, who happen to pick these discs up for old time's sake.