Right now in my sleepy-time playlist I've got some Ben Harper, some Old Crow Medicine Show, Elliot Smith, Beck, The Seatbelts, Tom Waits... multiple songs by one artist usually.
The Chemical Bros, Ephriam Lewis' "Skin" album and NIN's calmer songs like "A Warm Place" and "The Frail"
I don't fall asleep to music much anymore but when I do I like the following: Ozric Tentacles Mediaeval Baebes Dead Can Dance Peter Gabriel - Passion (Last Temptation of Christ soundtrack) Gong Fields of the Nephilim - Elizium
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