hahah. My high school, couple years back, had this webfilter named Bess. It worked soo well that teachers couldn't even get to the websites that they wanted. It would effect alot of classrooms where teachers went to go display something they had looked up from home and they weren't able to access it. I used anonymizer.ru and was one of the only people who surfed freely in my school. Most of the kids knew what I could do. It gained me a mini-rep. So when I saw so many teachers getting frusterated in class I would kindly offer them my help instead. Behind closed doors of course.
They enjoyed that and I offered my services widely. Sometimes being pulled out of a class to go help a teacher across the hall.
Ohh...naive school IT guy, you didn't like me much did you?
Reminds me of another time I installed a keylogger on all the computers in the labs and found a backdoor out to email the collections to a secure email address everyday. Pretty much a quarter of the school used those computers after school and I had quite a collection...I didn't ever do anything too malicious with the info tho. Just kick people off their own AIMs and laugh at them, and only if we were friends =)