I have a minor obsession with challenging, complex music. The genres of progressive rock and jazz fusion are good starting points for this type of music. Bands and artists I think are really amazing include:
Frank Zappa, Mike Keneally, Ruins (or nearly anything else Tatsuya Yoshida does -in fact I think Koenjihyakkei is the greatest thing going right now), Django Bates, Miriodor, Interference Sardines, and Sleepytime Gorilla Museum.
Since I started working at Berkeley, I've found the BayProg website to be a great resource. One of the guys I work with is Matt Lebofksy, and he's a musician with prog tendencies too. You should also check out Heavy Ethics, a band that combines jazz and prog into something really great. My friend Chris Norman is the bassist/guitarist in that band.
I have a page on the Ruins Prog Rock Medley that appears on their albums, Refusal Fossil and Pallaschtom.To see what's in my current collection, click here.
If you want to find out about concerts, check Pollstar.
I'm not a movie nut as much as I am a music nut, but I use the Internet Movie Database a fair amount.
If you want to try something really fun, go to Star Links and see what the shortest route between two movies stars is.