These are just my opinions on the Halloween specials, ranked worst to best. Feel free to share your own ranking! Also, I haven't seen The Scoots or Tegridy Farms Halloween Special so I've left them off the list.
6. Sons a Witches
This one was just kind of boring to me. I get the joke, about witch hunts and all, but it didn't particularly stand out to me. Also, it really frustrated me that Cartman never talked to Heidi about what was bothering him. Being upset about her taking a long time to get ready is not bad thing, but bottling up his emotions and instead trying to get her kidnapped by a witch is obviously very wrong. I just don't care about Cartman being a bad person at this point. It's not funny to me anymore.
5. A Nightmare on Face Time
This episode actually got a few laughs out of me, particularly the scenes where Cartman's costume kept getting mistaken and everyone treating Stan's iPad as though it were a real living being. Basically any time the kids were on screen, I was enjoying myself. However, the scenes with Randy at the Blockbuster were so excruciatingly unfunny that it really dragged the whole episode down. I suppose I found Shelly burning the store down kind of amusing, but other than that I just couldn't care less. Randy isn't an entertaining character to me. Moving on.
4. Hell on Earth 2006
Now here's a Halloween episode I can get behind. I love South Park's depiction of Satan; in fact, I can't think of a single appearance of his that I haven't enjoyed. Butters and Biggie Smalls were also pretty great. This episode wasn't perfect, but there was nothing about it that I strongly disliked.
3. Pinkeye
This episode is truly iconic, and a solid start to South Park's holiday specials. My favorite part was probably Cartman showing up to school dressed as Hitler (and subsequently being turned into a "spooky ghost,") and I absolutely love Chef's parody of Thriller. What else can I say? It's classic South Park. The few problems I have with it are just problems with the early seasons in general, for example the pacing leaves a bit to be desired, but all in all it's a great episode.
2. Korn's Groovy Pirate Ghost Mystery
This episode is a lot of fun, and the more original and interesting story is what puts it above Pinkeye for me. I love that everyone though Korn was satanic and evil when they actually ended up being a wholesome parody of Scooby Doo. (Also the fact that the real members of Korn did the voices is just... so great.) And if I'm being honest, I'm guilty of acting a little bit like Cartman by getting excited for Christmas in October, though at least he has the decency to wait for Halloween.
1.Spookyfish
I'm sure it's someone of an unpopular choice for the number one spot, but this episode just really works with my sense of humor. It's arguably the most original Halloween episode, with little to no references to pop culture or social issues aside from Barbara Streisand's Spookyvision (which I found hilarious.) One scene that always stuck out to me was the "God, I hate you, Kenny." His hatred was just so unadulterated and pure, I love it. And who could forget Evil Cartman's friendship song? (Well, I'm sure a lot of people forgot it, but I didn't!) This is both my favorite Halloween and season 2 episode. It's just one of those episodes that really stuck with me even though I've nearly finished the series.