1. Because he was the cutest athlete of all time.
He played soccer at the College of William & Mary, from which he graduated in 1984.
2. And he even made this haircut look semi-decent.
3. He's a self-made comedian.
After college, Stewart worked as a contingency planner for the New Jersey Department of Human Services, a contract administrator for the City University of New York, a puppeteer for children with disabilities, a soccer coach at Gloucester High School in Virginia, a caterer, a busboy, a shelf stocker at Woolworth's, and a bartender as he honed his comedy act at places like the Comedy Cellar.