1. Season 2, Episode 5: Halloween
As the first halloween episode on the show, this episode embroils us in a tension filled office with rumours of downsizing. Michael deliberates over who he’ll have to give the axe, while Pam and Jim post Dwight’s resume on the internet in an attempt to get him transferred. Personally, this is my favorite Halloween episode of the Office because it encapsulates everything that makes the show funny: its awkwardness.
2. Season 5, Episode 6: Employee Transfer
This episode focuses on Michael dealing with Holly transferring up to Nashua. Pam is working at corporate while balancing art school, and quickly comes to the realization that she’s the only one dressed up for Halloween (as Charlie Chaplin? Or Hitler? Hard to tell). Season 5 is also the height of Andy and Dwight’s rivalry, and we see their hijinks as Dwight dresses up as a Cornell student just to get under Andy’s skin.
3. Season 7, Episode 6: Costume Contest
This is probably my second favorite Halloween episode, and it’s Steve Carrell’s last Halloween episode before his departure later in season 7. There’s just a lot going on– Michael is angry with Darryl for going behind his back to pitch an idea to corporate, Pam plans the Halloween party, and the winner of the costume contest wins a coupon book which creates a lot of buzz and excitement. We see a lot of hilarious costumes, like Gabe as Lady Gaga, Kelly as Nicki Minaj, and, of course, Oscar as the “rational consumer.” Good one! Hot boy Danny Cordray invites everyone to his bar which creates even more tension since Danny and Pam had a (one date) dating history. And as always, we get an adorable Pam-Jim moment when Jim finally caves in and dresses up as Popeye once he realizes how lucky he is to have his “dorky” wife.
4. Season 8, Episode 5: Spooked
Ugh, what a terrible season. Robert California’s presence really irked me and changed the vibe of the show. Robert makes a visit to the office for their Halloween party planned by a very stressed out Erin (in her totally adorable Wendy’s costume). This is at a weird point in Erin and Andy’s relationship where he had a girlfriend but she still had feelings for him. It’s awkward, and creates an uncomfortable power dynamic that is definitely well-portrayed in the show. Robert asks everyone about his/her biggest fears (Kelly’s is dying alone, Meredith’s is Jim) and crafts an elaborate horror story to leave everyone very spooked, indeed.
5. Season 9, Episode 5: Here Comes Treble
Ugh pt. two. Season 9 was such a disgrace to this show, but that’s a story for a different time. This episode is chock-full of tension– Jim spends half of his and Pam’s life savings on his new startup, Andy deals with the fact that he’s not in college anymore, Erin sees some of the deep flaws in her boyfriend, and Dwight chases down a drug user somewhere in the office after finding a pill on the ground. While this episode definitely isn’t anywhere in my top favorites, the a capella is pretty good.