Billy Madison (1995) / Happy Gilmore (1996)
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. Adam Sandler stars as Happy Gilmore in the over-the-top comedy that scores a hole in one for hilarity. After his dream of stardom on the hockey ice melts, Happy Gilmore discovers he has a gift that could bring him glory on the greens. Trouble is, with his hot head and hard-hitting drives, Happy doesn't just play golf - he destroys it. With the help of a retired golfer (Carl Weathers) and hot publicist (Julie Bowen), can Happy perfect his game and tame his temper to win the tournament prize money?