I've gone to Jason since I moved to Madison almost 5 years ago. I even have moved to Milwaukee temporarily, and I still come back just for his haircuts. Here's why:
Whatever I have him do with my hair, it looks good, and I get tons of compliments from people I don't even know.
He is good at identifying problem areas with your hair (e.g. cowlicks) and knows exactly how to cut them to fix them.
He works really well with my hair - long, slightly wavy. AND he works really well with my needs: I don't like to style my hair or even dry it after I shower. He cuts my hair to accommodate my casual approach to hair-care.
I can give Jason a lot of direction, or very little ("do whatever you feel like...just let me know first", or "what are the cool kids doing these days") and he always makes it look good.
And, he knows all the cool kids' haircuts.
Good relaxed conversation in the meantime.
Worth every penny.