Tyrannosaurus Rex - Unicorn
Nick Drake - Bryter Layter
Harry Nilsson - Nilsson Sings Newman
Henry Mancini's Sunflower soundtrack

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While I generally prefer instrumental stuff for sleeping, I just remembered this one is nice to play, as it's very peaceful.

Grizzly Bear - Veckatimest

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Good call on Grizzly Bear
Ocean Rain-Echo & The Bunnymen

gotta say i'm pleasantly surprised that i can still turn people onto Boards of Canada now hehe

a few others i like passing out to

Tortoise - Beacons of Ancestorship (it's been my pass out soundtrack since i got it in July)
Air - Moon Safari (although their most recent album Love2 might be just as good, only heard it once but it renewed my interest in the band after a few lackluster releases. Pocket Symphony was weak.)
Esthero - Breath from Another (late 90s Canadian trip hop, more eclectic than dark, most definitely a late night album)

Good choice, would you recommend anything else by her?

I think I'd have trouble sleeping to this one as I find it more abrasive than their others.

Esthero is kind of hit and miss. her debut turned out to be a one-shot with her producer Doc. either way, her newer stuff is a bit more eclectic, mostly bordering on modern 'r&b'. actually haven't heard her last full length, only the single and ep that came out ahead of its much delayed release.

as for Tortoise i find the newest one to be a significantly different listening experience when i have it cranked through headphones and when it's at sleep volume through speakers. a lot of the layers get lost at a lower volume and the tracks become stripped down to their core elements which makes for a more ambient listening experience.

Ah yes. Well you see I'm a Tool addict, so I usually listen to tool anyway, fall asleep, and start dreaming about strange creatures with transparent skin and unusual body organ placement.

I can't recommend a specific album necessarily, but I often like to drift off to sleep to something with folksy guitars and a nice mellow voice...like Jose Gonzalez or John Martyn. Or some instrumental blues album. The rhythm of the guitars does it for me I think.