"Freak Strike"
Season 6, Episode 3

We've already applauded Stewie Griffin's cross-dressing exploits in Family Guy, so of course we have to do the same with Cartman. Unlike Stewie, Cartman wasn't exploring his preferences or pushing boundaries when it came to gender, but was trying to act outrageous enough to "win" a prize on the Maury show. Still though, props for the leopard top and trendy "pixie" cut à la Amber Rose.