16. The "Rapists And Murderers" Gag
Easily the most risque gag from the fifth season was a dialogue in which George Michael (Michael Cera) and Maeby (Alia Shawkat) discuss their grandma's twisted sayings.
They recite a particularly disturbing one: "They should take all the rapists and murderers and put them together on an island, and all the murderers can be raped and all the rapists can be murdered until you only have either two rapists left or one (raped) murderer, but who cares about him?"
Later, Lucille (Jessica Walter) is talking to her court-appointed therapist, Tobias (David Cross), and she asks him, "Am I horrible for saying these things?" Tobias says, "No, but I was doing the math and I still think you're gonna have a problem with this final raped murderer." Lucille's response? "But who cares about him?"
There's even another random gag along similar lines in the season's third episode, when George Michael visits Wetzel's Pretzels in Mexico and an employee jokes about raping and murdering (possibly a reference to Donald Trump calling Mexicans rapists).
A little overboard? Perhaps. Hilarious? Definitely.