When I lived in Boston as a college student, I used to go to this high end placed called "John Delaria" (sp?). It was on par with a Vidal Sassoon salon. I paid $20 for a great cut, always looked good, and only had to cut my hair about three times over a 9-month period. It was expensive for a starving college student, but hey, it made it easier to get laid.
Now I go to a $10 Supercuts kinda place and rarely do I get a decent haircut. But there isn't anyplace around here that does a great job for even $20. You are looking at $75 minimum of the kind of haircut I got back in Boston.