We had the janitor dress up in an ugly shirt, skirt, over his janitor clothes, add an ugly purse and wig. Then we have Mrs. ___ hand out the popcorn, soda, etc. We advertise it as a "classroom party delivered by a Special Guest". Everyone laughs a lot!
I've never been a fan of anything that disrespects an adult role model in a school. I think it's the wrong message to send to the kids.
Instead, consider positive rewards like, "Principal for a Day" or getting to eat a special lunch with the principal or the teacher in the office conference room, the teacher's lounge, or as a picnic outside. Getting taken to the movies (The "Meatball" movie is out now!) by the teacher or principal.
We are looking for a reward type of activity to follow our fundraiser. I know many have done the pie in the face, kiss a pig, or sleep on the roof routine. What other ideas are out there?