I couldn't really put these in strict hierarchical order, but I might be able to group them in some sort of coherent fashion. So the breaks represent steps in quality (from highest to lower); within each group, the albums are simply alpha by artist:

The Flaming Lips: The Soft Bulletin

Macha See it Another Way

The Magnetic Fields 69 Love Songs

Those Bastard Souls Debt & Departure

XTC Apple Venus Vol. 1

Notable to me is that three of these are incredibly ambitious efforts (the Lips, Magnetic Fields, and XTC) - and all three pay off handsomely. Neither Macha nor TBS are slouches in the ambition department either...

Next:

Anton Barbeau A Splendid Tray

The Hang Ups Second Story

The Rock*a*Teens Golden Time

Sparklehorse Good Morning Spider

Wilco Summerteeth

Hmm... looks like the more songwritery stuff is registering just a tad lower, with my preference leaning toward the more colorfully arranged releases and the more emotionally intense as well.

These next are all excellent, but for various reasons didn't cohere or impress quite as much as the above did:

Jason Falkner Can You Still Feel, Guided by Voices Do the Collapse, Lilys The 3-Way, Low Secret Name, The Olivia Tremor Control Black Foliage, Stereolab Cobra and Phases Group Play Voltage in the Milky Night, David Sylvian Dead Bees on a Cake

Some stuff I haven't noticed being mentioned in others' lists (which should be):

Bows Blush, The Fly Seville Carousel, Labradford E Luxo So, Sunset Valley Boyscout Superheroes

Honorable Mention:

Aden Black Cow, Frank Black & the Catholics Pistolero, Joe Henry Fuse, Kristin Hersh Sky Motel, Robyn Hitchcock Jewels for Sophia, Yuji Oniki Orange, Tobin Sprout Let's Welcome the Circus People, Richard Thompson Mock Tudor

And actually, there are probably 5-10 more that I listen to quite a bit - or wish I had time for! (That's the biggest trend in '99 for me - not enough time to really enjoy what I like!)

stuff of impeccable reputation I haven't heard yet:

most recent by Robert Pollard, Superchunk, Quasi, Tom Waits, and probably a zillion others I'm completely overlooking at the moment.

Trend I most want to see die in 2000:

Asshole rap-metal (and its fratboy fans). I don't suppose I'll get too much disagreement on that here...

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