I do play the same stuff a lot, but I do try be less repetitive. Lucinda Williams, Fiona Apple and Tuneyards lately. Also a lot of jazz – Miles Davis, Anita O’Day and Nina Simone.
I have a large iTunes library, so to stay out of a rut I pick one song and choose Start Genius. That creates a playlist that always includes songs I’ve been neglecting.
Also I listen to a low-power FM station in the car. They rarely play anything familiar to me.
AndI listen to the KCRW Eclectic 24 a lot Internet stream for more unfamiliar music.