Principal Takes a Holiday (1998)

A rowdy high school senior risks losing a $10,000 gift his parents promise him for graduation if he can complete the year without getting in trouble by getting caught by the principal in a prank. However, when an accident befalls the current principal, the senior goes and finds a drifter to show up at the school as the new principal to get his records erased.

The movie Principal Takes a Holiday, released in 1998, features 1 song from Mark Mothersbaugh.