need name of old pc game!?

I used to play this game on pc about 10 years ago, it was about this kid name William or willy or something like that. he was a brunette with a yellow shirt and I remember the game starts where you're in school and you have to make choices and if you're too bad then you go to the military and they shave your head. and you travel around via a skateboard. does anybody know what i'm talking about?