37. Billy Madison (1995)
Director: Tamra Davis
Stars: Adam Sandler, Darren McGavin, Bridgette Wilson, Bradley Whitford, Josh Mostel, Norm Macdonald, Steve Buscemi, Chris Farley, Jim Downey, Theresa Merritt
Grown-ass grade schooler Billy Madison (Adam Sandler) is basically retarded in this movie, but that's not why it's offensive. His horny, obese black maid, who would service his every need, from lunch to, um, other stuff ("Ah thought AH was yo' snack pack, Billy!") still has Hattie McDaniel turning in her grave.