19. The Red Badge of Gayness (Season 3, Episode 14)I'll be honest. I'm not sure that this episode would be featured in my Top 25 list if it wasn't for my own connection to Charleston, South Carolina.
I think that some of the previous episodes on my list are funnier and probably stronger overall, but at the end of the day, The Red Badge of Gayness takes this spot. Aside from having both lived in and frequently visited Charleston before, I grew up with a pretty decent personal education on the American Civil War from my dad.
While there are plenty of other episodes that show Cartman's genius ability to manipulate others to fulfill his own selfish desires, I've always enjoyed this one because of its historical connections and satire. The idea of resurrecting the Civil War via drunken Confederate re-enactors is
genius to me. I especially love the moment when Cartman and Co. invade Fort Sumter (which is located in Charleston) and reinforcements come to Cartman's aid via the South Carolina Militia. As someone who has interacted with a lot of rednecks and country boys, I can't help but picture a lot of familiar faces participating in such a charge.
Oh and this episode has one of my personal favorite Kenny deaths. It's simple, but hilariously effective.