Regina Spektor, I've been discovering her stuff over the last few months and I've reached the point where I know roughly all of it. As I think is expected in this thread, all I can really offer here is possibility that blog-reading choices vaguely correlate with musical preferences. Her lyrics are pretty non-inane, especially upon repeated listening. Her variance of musical style is pleasing to me, makes it fun to play and listen to. Nothing especially Less Wrong-y, but I might be forgetting something. Though I don't think I know any composer at all who's (consistently) Less Wrong-y. She has a wild imagination and has written songs about being robots. She's one of those artists whose discography is a tapestry of varied and wonderful worlds that I can never really appreciate unless I'm in the process of listening to it, always a process of both rediscovery and familiarity. (She often writes in the first-person as non-Regina people, from fiction, the bible, or anonymous people; more than half of her songs are probably from the perspective of a different person). There are also lots of moments in her various songs that strike me in the right way, that capture some complex emotion I had never put into words, which gives her songs a sense of salience and intelligence. Some especially enjoyable songs: Us very uplifting, makes you think; Call Them Brothers the man singing is her husband, I like the eeriness; The Party, uplifting, pretty; All the Rowboats, she makes cute noises, quite fast. Back of a Truck, from her unusually jazzy first album.

Disclosure: I play and especially like piano so appear to be skewed towards liking such artists.