39. Daniel Desario
Show (Air Dates): Freaks and Geeks (1999-2000)
Actor: James Franco
As the leader of the Freaks, the rebellious Daniel Desario dons the sartorial signifiers of any burnout: stocking caps, combat boots, a distressed denim jacket, tees layered over waffle shirts, and a black leather jacket that he scuffed up himself. Add the fact that he plays guitar and he's about as cool as they come in high school.