Billy Madison (1995)

Adam Sandler stars as Billy Madison in the outrageous comedy where the subject is always fun. 27-year-old Billy Madison must repeat all 12 grades of school - in just 24 weeks - to earn his father's respect and prove he has what it takes to run the family's multi-million dollar empire. Along the way, Billy falls for his 3rd grade teacher (Bridgette Wilson), gets kicked out of school and must face-off with his nemesis…not to mention a pesky penguin.