Scary Movie is a classic for people my generation and since it has a rather juvenile style of comedy, the franchise gave us some good wedgie jokes we can enjoy today. Two female wedgies and one male.
Scary Movie 2 wedgies:
When Cindy decided she wanted Buddy to be just a friend, she never realized what being a "friend" meant to a young male. He immediately pranked her by giving Cindy a wedgie, grabbing her underwear and yanking it comedically.
The second wedgie is actually one that is given to Buddy by the ghost near the end of the movie.He reunites with the girls but an unknown force pulls him by his tighty whities and a ghost screams "Wedgie!" Buddy is given a hanging wedgie until he is saved by Cindy.
Scary Movie 3:
Only one wedgie is given in Scary Movie 3. At the beginning of the movie, two girls are gossiping and their argument then playfully turns more violent and vicious, until one of the hotties gives the other one a wedgie, yanking her friend's pink panties. The phone rings and the distracted giver lets the panties snap back.
You can see the official clip here at 1:33
Great scenes, two of the most prominent female wedgies in media and quite funny scenes as well!