Belle & Sebastian - If You're Feeling Sinister
Any of the first three (four? all?) Belle & Sebastian records could have made it onto my list, but Sinister represents the most well-rounded collection of their songs and possibly the strongest articulation of the band's unique magic. Perfectly capturing the brightest moment of a fresh spring day in the life of a neurotic youth, this album is essential.
Liz Phair - Exile in Guyville
Grainy, half-remembered rock & roll reveries wrapped up with brazenly strong lyrics and endless hooks. This album paved the way (no pun intended) for the same kind of late-night, city scene energy that filled Pavement's Crooked Rain, Crooked Rain and would later inform artists like the Yeah Yeah Yeahs and Cat Power.
DJ Shadow - Endtroducing...
This pastiche of sample-based instrumental hip-hop had a more uniquely colorful and daringly piecemeal perspective than anything that came before it. It opened doors for hip-hop producers and indie experimentalists alike. Without its kitchen-sink palette of sounds, things might have been different for the J Dillas and Madlibs of the world, and a whole later wave of sample-happy indie acts.
Panda Bear - Person Pitch
Animal Collective were on the brink of breaking through into enormous mass appeal but still delivering nervous and static-y albums like Strawberry Jam when bandmember Noah Lennox broke the doors down on 2007 with this solo album of '60s chamber pop samples and meditative harmonies. This album single-handedly (for better or worse) inspired entire subgenres of beachy, reverb-crusted indie sounds, and still serves as a gold standard for any and all bedroom collage-pop that followed it.
Smashing Pumpkins - Siamese Dream
With the Pixies' Doolittle and Nirvana's Nevermind both released a few years outside the constraints of this list, Siamese Dream gets the prize of most important mainstream alternative guitar rock gate-crasher here.
Beck - Sea Change
Making a perfect breakup record without wallowing in the torture of it all requires a lot of restraint and precision, all of which happened on this lushly heartbroken album by one of the most shape-shifting superstars of the last 20 years.
Björk - Vespertine
Crystallized perfection more human than the mechanical beats of Homogenic and more even-tempered than the wild fires of Post.
OutKast - Speakerboxxx/The Love Below
I actually only like Andre 3000's half. But not just "Hey Ya!"!!!!
Black Dice - Beaches & Canyons
A silently definitive album by what I predict will be viewed in hindsight, as one of the most influential bands of my time. A huge shift from the group's noise and thrash beginnings into a multicolored nature trip that bands are just now getting around to ripping off ten-odd years later.
Squarepusher - Feed Me Weird Things
Glacial IDM rhythms competing with hectic funk basslines didn't keep Squarepusher's debut from feeling musical, melodic, and even a little bit emotionally venerable in a strung-out kinda way.
Guided by Voices - Bee Thousand
The sonic equivalent of drinking a six pack of cheap beer on an empty stomach at a Memorial Day barbecue while listening to The White Album, only remembering the first 30 seconds of any given song (and feeling great about it!).
Boards of Canada - Music Has the Right to Children
A perfect album in the electronic category, partially responsible for the current over-use of the word "gauzy" in music journalism.
The Notorious B.I.G. - Ready to Die
A classic, era-defining moment for hip-hop, with unparalleled attitude, flow, and storytelling flair.
The Strokes - Is This It
Room on Fire is great, too!!
The Microphones - The Glow, Pt. 2
This album achieved some strange, impossible balance between the sprawling epic feel of Sonic Youth's Daydream Nation and the hushed in-one's-own-head pop of its Pacific Northwestern indie cultural backdrop.
Joanna Newsom - The Milk-Eyed Mender
Almost as if out of thin air this album appeared in 2004; trembling and soft yet unquestionably powerful songs dense with lyrics of pure poetry, all flowing out of a single harp and this lady with a mesmerizingly strange voice.
Wu-Tang Clan - Enter the Wu-Tang (36 Chambers)
Still one of the most energetic albums ever made, hip-hop or otherwise. The electricity and hunger on every rhyme are matched only by the innovation of the beats.
PJ Harvey - Rid of Me
Housed in Harvey's crushingly raw songs of desperation, obsession, sex, and betrayal was enough emotional dynamism to inspire a generation.
Jawbreaker - 24 Hour Revenge Therapy
A masterpiece of literary punk, this album finds unlikely beauty in the midway point between the drunken ruminations of the Beat Poets and the studs and mohawks of the mid-'90s Gilman Street punk scene.
The White Stripes - De Stijl
While most lists will point to Elephant as the Stripes' brightest moment, I think a factor of the duo's immense success that often goes unmentioned is just how freakishly weird they were. Conceptually, sonically, in performance and as people, Meg & Jack were genuinely a little bit not right, and no more honest an expression of their somewhat ill-fitting perfect cool was made than De Stijl. Recorded at home by the band, the songs are among the most lasting and most introspective, with more personality and guts than any of their other records managed.