TOP FIFTY ALBUMS OF THE '90s: # 40-31

40. Liz Phair – EXILE IN GUYVILLE
No longer crossing my fingers for a middle-aged masterpiece from this woman given her recent dubious exploits, I’m still thankful I’ll always have this brash, clever, bratty song cycle to return to: a raw, arresting, unapologetic blow-jobs-and-all account of a 26-year-old woman in a male-centric world.



39. Cibo Matto – VIVA! LA WOMAN
If Yoko Ono had collaborated with the Beastie Boys, this sample-heavy concept album about food might have materialized. Goofy, surreal and occasionally menacing (all at once on “Birthday Cake”), it makes me nostalgic for a time when MTV would air something so deranged, even if it was only on 120 Minutes.



38. Ani DiFranco – LIVING IN CLIP
Since her many, many studio albums only sporadically nail down her onstage energy and presence, this double live album remains an essential overview, even more so for capturing the spontaneous, intimate, mesmeric vibe of being there like few other live albums.



37. Jill Sobule – JILL SOBULE
The original, way better “I Kissed a Girl” is only an entry point into an enchanting world of sketchy boyfriends, mysterious co-workers, daydreamers and other lovingly drawn winning losers - it's a shame her Major Record Label didn't help her much in becoming more than a novelty one-hit wonder.



36. Sam Phillips – CRUEL INVENTIONS
A more introspective and acidic Phillips emerges on her second secular album. Like ever-shifting puzzles, the songs simmer with both lyrical and musical intricacies, but they never obscure such olive branches as a gorgeous Van Dyke Parks string arrangement or a declaration like “If I told myself I believed in love and that’s enough, I’d be lying.”



35. Ivy – REALISTIC
On their full-length debut, this French female-fronted trio comes off less like the pop sophisticates they would evolve into and more like Mazzy Star at a slightly quicker tempo…which proves a brilliant idea once the actual songs emerge from the overall heavenly, atmospheric gauze, hitting their targets with gentle aplomb.



34. Suzanne Vega – NINE OBJECTS OF DESIRE
Many fans loathe her two ‘90s albums produced by now ex-husband Mitchell Froom, but I love how his elaborate, quirky settings occasionally scrape against her clean, unfussy vocals. Here, her lyrics seem particularly inventive as they craft unique metaphors out of such standard subjects as sexual attraction (of various shades) and maternal love.



33. Jen Trynin – GUN SHY TRIGGER HAPPY
Witter and wiser than most alt-rock chicks of her time, Boston-based Trynin deserves to be more than a footnote. Her second (and final) album crosses Chrissie Hynde (at her most self-assured) with Joni Mitchell (at her most confessional). It actually rocks while projecting vulnerability and subtlety, which perhaps is why it has aged so well.



32. Massive Attack – MEZZANINE
Their first two albums invented and perfected trip-hop, but their third proved far more prescient. Suffused with an encroaching dread verging on decay, it negated any feel-good optimism of its time, instead anticipating the darker days ahead. And yet, it’s all so seductive and alluring—not for nothing did “Teardrop” become a TV show theme song.



31. K.D. Lang – INGENUE
Never a genre conformist, Lang’s shift from country to torchy adult pop still radiates bravery in an environment where far too many artists allow themselves to be boxed into neat, identifiable packages; it also succinctly creates a special, singular space for her nuanced, dramatic voice.