Bully (PS2)

Hint - Dunce Hat
Go to the boys locker room and turn on the showers for a free dunce hat. You could also try... Nah, better leave that alone.

Hint - Easy Gym Challenge
Beat all the challenges in the gym, and once you've done this, you'll be able to challenge everyone at anytime. The key to the easy money is to go up to the line every time, press Circle to jump, and while in mid-air, press X to throw. It's a devastating thrown that'll smash 'em over every time.