The Office Halloween Episodes: A Definitive Ranking

If you have only watched The Office in reruns (we see you, Gen Z), you might not even know that “Koi Pond” is a Halloween episode. That’s because all the Halloween stuff comes in the cold open, which subsequent airings have tried to avoid. The reason? Michael Scott’s inappropriate humor was too inappropriate for audiences. During a children’s tour of Dunder Mifflin’s “Haunted Warehouse,” Michael (who is dressed as the characters from the 2009 SNL digital short “D*ck in a Box”) decides the best way to scare kids is to pretend to be dying by suicide, ending the dramatic display with a PSA about how “suicide is never the answer.”

It’s also never funny, so... despite Jim’s clever “Facebook” non-costume, and the deadpan humor of Darryl joylessly taking kids on the tour, we’re putting this at the bottom of the list.

In this last Office Halloween episode, Andy is now the boss at Dunder Mifflin and reigns over the Halloween party festivities. Andy being Andy — a man who hinges his personality on the fact that he went to Cornell and did a cappella there — he has accomplished this by inviting the latest incarnation of his Cornell a cappella group, Here Comes Trebel, to sing. The whole ploy is a way not only to relive his glory days, but to get to sing the lead part in a rendition of George Michael’s “Faith.” It doesn’t pan out, despite the fact that Andy has, naturally, dressed up as the legendary singer to drive the point home.

While Halloween is the backdrop for this episode, the plot doesn’t exactly hinge on the Halloween-ess of it all. But we love Andy’s inability to grow set against Erin, his girlfriend at this point, starting to... and also Dwight getting his head stuck in a jack-o-lantern is just *chef’s kiss*.

As with “Koi Pond,” the Halloween aspects of this episode are all set within the cold open. Pam, living in New York as she attends art school, finds herself out of place in Dunder Mifflin’s corporate office where no one else has dressed up. She notes that she can’t wash off her mustache, as she put it on with grease paint. “I can’t even take off my hat,” she deadpans, demonstrating “because then I’m Hitler.”

We also love Creed, Kevin, and Dwight all show up as Heath Ledger’s Joker and Kelly needing physical support to walk on the high heels she wears as part of her Carrie Bradshaw costume.

In this episode, Steve Carrell’s last Halloween episode of the series, the whole office is competing in a costume contest to win a glorious prize the “$15,000” Coupon Book for local businesses. (Oscar seems to be the only one who realizes the book is actually worth maybe $40 despite being advertised as holding $15,000 worth of savings.)

Everyone trying to get Stanley to notice literally anything makes for some great laughs, as do the groups frequent costume changes throughout the episode. We also really liked that Jim, who always considered himself “too old” for costumes, even when he was a kid, puts his cool kid persona aside and puts on the Popeye costume to coordinate with Pam’s Olive Oyl costume. (He even gets Cece in a Sweetpea costume.)

A lot of people think of Halloween costumes as a way to see how people see themselves, and in “Halloween,” the first ever Office Halloween episode we surely do get to see Michael Scott at his Michael Scottiest. Jan has told him that he has to let go of someone on the team by the end of the month... he has chosen to wait until the very last minute, which also happens to coincide with the office Halloween party.

It’s a premise — demonstrated by several failed firing attempts — that perfectly captures Michael’s ineptitude and the fact that he’s motivated almost entirely be a desperate desire to be loved and not make anyone upset. Also, the incongruity of interpersonal conflict in Halloween costumes is comedy in its purest form (for another example of this, see also Dick Van Dyke’s guest spot on Golden Girls as a clown-lawyer).

We’d also be lying if we didn’t admit the end scene, in which a dejected Michael gleefully hands out candy to adoring trick-or-treaters is simultaneously heartwarming, poignant, and melancholy.

In this episode, Erin has been tasked with planning the Halloween party. It’s nerve-wracking enough to try to put together a celebration that will impress Andy, whom she has feelings for, but company CEO Robert California is coming with his son, too. In short order, Erin’s party is deemed too childish, prompting her to try to come up with a “scary and sexy” Halloween.

There’s a lot going on in this episode that’s really funny. Jim and Pam’s ongoing arguing about the existence of ghosts. Gabe’s “Cinema of the Unsettling” movie — an avant garde film genre with unsettling images and no plot... which for some reason includes shots of Oscar’s grandma and Stanley getting into his car. Erin’s earnest but naive attempts at making a more “adult” party (hint: pornography is involved); Bert California’s bizarre antagonistic friendship with Dwight; and, of course, Robert California’s spooky story ending with the classic line “I’m fine, b*tch. I’m fine.”