1. "Tropic Thunder"
Ben Stiller not only convinced Robert Downey Jr., the most bankable star in Hollywood, to wear blackface in his 2008 film Tropic Thunder, but he got Tom Cruise to put on a fat suit, a bald cap and and play a profane, stereotypically Jewish film executive. Both of those could have been career-ending decisions, but Tropic Thunder is so damn hilarious that few criticized those details. It's about a group of privileged actors shooting a movie about the Vietnam War that find themselves in the middle of an actual war, sort of like Galaxy Quest in the jungle. The movie was so popular that this poll received multiple votes for Simple Jack, the fake movie within the world of Tropic Thunder, in which Ben Stiller played a mentally challenged child name Jack. The few clips we see of Simple Jack in Tropic Thunder are some of the funniest parts of the movie, and they manage to make the movie somehow even more wonderfully anti-PC and offensive.