I have a friend from highschool who won the 168 Hour Film Festival's award for Best Original Score last year. Another film (Ctrl Z) she scored is a finalist in the Sundance Film Festival 2008 Delta Fly-In Movies Competition. That's pretty cool IMHO.
In a related vein, I recently saw Dan in Real Life. While I wasn't aware of it until the end, the entire film was essentially scored by Sondre Lerche ... whose music I've been falling in love with for some time now. If you haven't heard of him, you should have a listen.
Other music currently on repeat:
Vienna Teng ... pianist and singer/songwriter from Cali
Brett Dennen ... singer/songwriter who toured with John Mayer this summer
Paolo Nutini ... actually Scottish not Italian (& what could be better than a song with your own name in it)
And of course, I'm dusting off some classic Gordon Lightfoot and Joni Mitchell too. Wouldn't want to neglect some great Canadiana now, would we?
(If you want a great song for the holidays, find Sarah McLauchlan's cover of Lightfoot's Song for a Winter's Night.)