Early on, Giles tells Buffy that Halloween is actually supposed to be a supernaturally quiet night. Clearly that’s not the case in Sunnydale.
Season Two’s “Halloween” (which first aired on October 27, 1997) introduced us to Giles’ chaos-obsessed former pal Ethan Rayne (RIP Robin Sachs), who sells the Scoobies costumes that turn them into what they’re dressed as. There are great character moments in the costumes they choose. Willow initially dresses as a prostitute, bare mid-rift and all, but ultimately settles on ghost, no skin in sight. Xander’s camo’d out as a military dude. Buffy wants to dress like one of the girls Angel would’ve dated when he was human, an 18th century maiden. Willow is in the best and worst position once the spell starts: she knows who she is, but unfortunately is an incorporeal version of herself and cannot really affect much. Xander’s best moment is right when the magic kicks in. Nicholas Brendan’s switch from goofy teenage boy to take-charge soldier is pretty excellent—and it’s a good costume for this scenario as it gives him some tactical knowledge he might not otherwise have (and which he seems to retain in later episodes). Buffy…well, her costume choice does not lend itself well here and she is basically helpless. Cordy is a cat…but she’s not, because thankfully she bought her costume elsewhere. It’s the Buffyverse, so the stakes aren’t the only things that are pointed; the traditions of the holiday are used to great effect to build on these characters we’ve been falling in love with for the previous 17 episodes.
Season Four’s “Fear Itself” (which first aired on October 26, 1999) is probably the best ‘Ween celebration. Buffy and the gang attend a Halloween throw down at a frat house where panic and fear are the order of the night. And when told to dress as what scares her the most, Anya shows up dressed like a bunny. Classic. In this ep, Oz accidentally cuts himself and bleeds on a demonic symbol painted on the floor of the frat house, summoning a fear demon known as Gachnar. The house is locked down and the partygoers fears are manifested inside.
The season six “All the Way” episode (which originally aired on October 30, 2001) is in ways a fun distraction from the darker tone of the season, and it focuses on Dawn and her friend (Amber Tamblyn) hanging out with cute boys who turn out to be vampires. As ever, October 31st is used to establish deeper themes than candy corn and jack o’ lanterns. So many (pumpkin) seeds are planted this episode: Xander and Anya finally announce their engagement. Tara is getting concerned at Willow’s overuse of magic. Giles is concerned at how much Buffy is relying on him and how it may be stunting her growth, not only as the Slayer but as a functioning adult. We know how grim these stories are by the end of the season, so let’s enjoy the lighter moments while they last.
Buffy’s Halloween eps work so well because when a viewer is immersed in a specific season, the finer points of the plot really enrich and drive forward that arc. At the same time, the story in each episode is a nice one-and-done, where the Halloween mayhem is wrapped up good and tight by the time the credits roll, making any of the episodes perfect to watch on an October night.