5 of ‘The Office’ Halloween Episodes, Ranked by Greatness

Ooph, where do we even begin? There are so many subplots to this episode so let’s dive right on in.

The opening is definitely the highlight of the episode as Dwight (Rainn Wilson) wears a jack-o'-lantern on his head to play a prank on his coworkers (the only person he scares is Erin, aka Ellie Kemper, naturally). When Dwight tries to take off the pumpkin, he realizes he's stuck and enlists the help of Jim (John Krasinski)…who demonstrates smashing it off with a baseball bat. Clearly not wanting to go that route, Dwight decides to let the pumpkin rot off, which he estimates will take about a month or so.

As all the other office workers settle into their desks, we get a glimpse at their Halloween costumes. Pam (Jenna Fischer) is dressed as Dr. Cinderella to set a good example for her daughter, while Jim, per usual, isn’t dressed up as he’s meeting with investors for his new job (more on that later). Dunder Mifflin Sabre manager Andy (Ed Helms) is dressed as George Michael because he invited his Cornell University (did you know he went there?) a cappella group, Here Comes Treble, to perform for the office and is trying to act as their mentor. The group shows up and performs Michael’s Faith, one of Andy’s signature songs, and just as he’s about to start on his solo, Broccoli Rob (played by guest-star Stephen Colbert) pops up via webcam to take over. Because Andy is Andy, anger ensues.

Now dressed as a pig, Dwight finds an anti-anxiety pill on the floor and goes on a hunt to find the “madman” who it belongs to. Nellie (Catherine Tate), who’s a “hot version of Toby,” knows the pill is hers but doesn’t want to admit it. She entertains Dwight by joining in on the hunt.

While this is all happening, Jim goes out to lunch with a group of investors for his new job. He insists on putting in $10,000 (much more than he previously agreed to with Pam) even though the investing window has already closed. When Pam finds out, they begin to fight during the Treble performance. (We don’t know about you, but the argumentative plotline between Jim and Pam in the later seasons is such a stretch and we’re not here for it.)

The episode closes with Oscar (Oscar Nunez) (dressed as a crocodile, aka the Electoral College) kissing Angela’s (Angela Kinsey) husband, Senator Robert Lipton (Jack Coleman), behind the office building. He notices the cameras have caught them, gives a regretful guilty look and walks away.

The forced Jim/Pam fighting and lack of Michael Scott are enough to keep this Halloween episode at the back of the pack, with a last place ranking.

The only mention of Halloween in this episode is during its cold open, which is packed with fantastic costumes (and hilarity, of course).

In New York, Pam is the only one in a costume at Corporate. She takes on Charlie Chaplin, grease mustache and all. As if she doesn’t feel silly enough, she’s even more annoyed that she can’t remove her hat because then she resembles Adolf Hitler. (For the record, her version of Chaplin is pretty spot-on.)

Back in Scranton, Kelly (Mindy Kaling) is dressed as Carrie Bradshaw from Sex and the City but can barely walk in her high heels so Ryan (B.J. Novak), dressed as Wall Street’s Gordon Gekko, tries to win her over by helping her keep balance. Meanwhile, Stanley (Leslie David Baker) is only wearing a Creature from the Black Lagoon mask to hide the fact that he’s sleeping at his desk (no surprise there). The award for best costume go to Creed (Creed Bratton), Kevin and Dwight as they are all done up as Heath Ledger’s version of the Joker from The Dark Knight. Creed is by far the creepiest because, well, he’s Creed. Andy has gone all-out in his version of Rum Tum Tugger from Broadway’s Cats, while Jim is wearing normal clothes with a nametag sticker that says “Dave.” Oh, Jim. At least his perfectly timed facial expressions toward the camera make up for his hate of Halloween.

Sure, the cold open is what our Halloween dreams are made of, but the rest of the episode is, dare we say, average.

In the first Halloween episode without Michael Scott, new manager Andy tasks Erin with throwing a party that will impress Sabre CEO Robert California (James Spader). Robert arrives to the office with his son Bert, who says the party is set up for kids rather than adults. Naturally, Andy goes into panic mode and enlists the help of PPC vets (that’s Party Planning Committee for Office, novices) Phyllis (Phyllis Smith) and Angela to re-tailor the party. Erin worries and asks Gabe (Zach Woods) for help in making the party actually scary.

In between Erin’s party planning, Robert goes around the office and talks to each employee in his typical weirdly calm but intimidating fashion. In each of his conversations, he gains a piece of information (or uh, fear) about each employee, which doesn’t make any real sense until the end of the episode when he tells a horrifying ghost story using everyone’s primal fears, like Darryl’s (Craig Robinson) being buried alive or Kelly’s never getting married.

Erin succeeds in making the Halloween party scary, mainly because of Gabe’s ultra-creepy short film that depicts disturbing images with no explanation. Then everyone turns on Gabe when they realize there’s hidden footage of them in his film. Oh, and Pam believes in ghosts, which Jim can’t even wrap his head around.

If this list were based on Halloween parties alone, it would earn the top spot thanks to Erin, but unfortunately, the lack of Michael is really noticeable.

Ah, now we’re getting to the good stuff. “Costume Contest” takes home the second spot for best Halloween episode.

Things start out with quite a few costumes, but not because it’s Halloween. Jim realizes Stanley doesn’t notice anything that’s going on around him because he’s so consumed with his crossword puzzles…and lack of interest in work. To see how much they can get away with, the Dunder Mifflin employees pull out all the stops: Kevin dresses as Phyllis, Andy sits at his desk shirtless, Michael talks about a branch on Jupiter in a meeting where Stanley is sitting the opposite direction of everyone else and Dwight brings in a pony. The only thing Stanley does notice? When the clock turns five and it’s time to go home.

But now onto Halloween. For this year’s costume contest, Pam offers a Scranton-area coupon book worth $15,000 in savings as a prize for the winner. Oscar tries to be the voice of reason, but the rest of the office thinks the book is literally worth $15,000. This still doesn’t convince Jim to dress as Popeye to match Pam’s Olive Oyl. Throughout the episode, several employees change their costumes in hopes of winning the coupon book. Let’s all take a moment to appreciate Angela’s “hot nurse” (she is originally dressed as a penguin) costume and Gabe’s amazing impression of Lady Gaga complete with her signature hair bow and lightning bolt.

Later, Michael finds out Darryl went over his head and spoke to Gabe about a new sales idea (one that Michael previously shot down). He becomes more and more agitated and accuses Darryl of backstabbing him. Michael gets so angry he takes off his MacGruber costume and changes into Darryl’s old warehouse uniform to rally everyone in the office in calling him a backstabber.

We finally see Jim dress up as Popeye (and Cece as Swee’Pea) after he finds out Danny (Timothy Olyphant), the new salesman, didn’t call Pam back after a date four years earlier because he thought she was dorky. In the end, Oscar wins the costume contest (dressed in plain clothes as a “rational consumer”) when it’s revealed in Survivor-style interviews that everyone voted for him as a burn vote.

This episode hits all the notes: Michael being Michael, Oscar trying to prove everyone wrong and Jim finally giving in to wearing a legit costume.