oh man I remember the days of converting gamespy.com's IP to octal to get around the school's firewall block thing
Hell I even made a counter-strike map of the campus and surrounding suburban downtown where the terrorists bomb the school's proxy server so the students can have unrestricted internet!
Man that would have gone over so well nowadays...
edit: or the time I got around their EXE blocking by changing a bunch of strings in UnrealTournament.exe to look like Norton Anti-virus. Got a couple weeks' suspension for that!
The network admin (a friend of mine) told me he gauged his skill as an admin by how quickly I was able to break past whatever blocks he had in place.