There have been many television shows over the years that took Halloween more seriously than The Office ever did. From the Halloween Heists of Brooklyn Nine-Nine to the Treehouses of Horror of The Simpsons, Halloween has become a television staple over the years, cementing itself as one of the culture's most popular and beloved holidays.
On The Office, though, Halloween often served as more of a backdrop than anything. There were times when a costume contest took center stage, but it wasn't more important from a story-perspective than a feud between Michael and Darryl (for example). The same is true of The Office's first Halloween, which tasked Michael Scott with firing one of his employees. That being said, no one took the holiday less seriously than salesman Jim Halpert. Over the nine seasons of The Office, the lack of care Jim put into his costumes was always one of the show's most hilarious recurring gags.
6 Chris Bosh
In season eight's "Spooked," the only non-funny Jim Halpert Halloween costume was presented. After a great deal of anticipation for what the latest installment in the lore of Jim's costumes would be, there was a major let down when Jim not only took part in a group costume, but when the show decided to focus on Robert California for humor instead.
Season eight had lots of moments like these. It aired during the 2011-12 TV season, which was also one of the peak years for the Big Three of the Miami Heat. With the other sports fans of the office, Darryl and Kevin, dressed as LeBron James and Dwyane Wade, respectively, Jim donned a Chris Bosh Heat jersey. Yes, it was just the jersey, but it felt like a very deflating moment.
5 One Of The Men in Black Guys
In season nine there was a slight return to form for Jim's Halloween costumes. In "Here Comes Treble," the focus was on Dwight's pumpkin head, Andy's George Michael costume, and an appearance from Stephen Colbert as Broccoli Rob. Yet, there was still a moment that allowed Jim to throw in one last lackadaisical Halloween costume.
With his attention more focused on his new business venture outside of Dunder Mifflin, Jim took a look at his everyday outfit and ascribed himself to be "one of the Men in Black guys." Technically, it works. He does seem like the Tommy Lee Jones type.
4 Facebook
Depending on the version of season six's Halloween episode, "Koi Pond," fans saw, it might not be apparent that Jim ever sported a Halloween costume. Yet, there was still a version of the installment that centered the cold open around a Halloween tour through the warehouse.
There, Jim wrote the word, "book," on his face to go as Facebook for the holiday. Others thought he was "Bookface." While this scene has since become a deleted one, it's still canon to The Office and still an example of the ingenuity Jim could flex whenever he felt so inclined.
3 Dave
Aside from the Jeff Winger-esque dismissal of his Men in Black costume, this season five Halloween costume is surely the one Jim put in the least effort for. In "Employee Transfer," while Ryan went all-in on Gordon Gekko, Kelly committed to Carrie Bradshaw, and three employees immersed themselves in the Joker, Jim was simply Dave.
He became Dave by slapping a sticker on his chest. It was a sticker that read, "Hello, my name is," with a blank space for someone to write their name as an easy greeting. Instead, Jim co-opted it as a Halloween costume and scrawled in Dave. It's very dry, but very amusing.
2 Popeye
Now, considering the appeal of Jim's Halloween costumes is that he put no effort into them, this may seem like an odd inclusion so close to the top of the list. However, it's important to remember the two stages of Jim's Popeye costume in the season seven episode, "Costume Contest."
At first, Jim goes along with Pam's wish for a family Halloween costume (she's dressed as Olive Oyl and their daughter, Cece, is Swee'Pea) by simply putting a corncob pipe in his mouth and shrugging, "I am Popeye." However, when Pam's enthusiasm is later squashed, Jim decides to lift her spirits. He returns home to put on the entire Popeye ensemble and retrieve Cece. Not only was Jim partially careless, but it also resulted in a sweet moment and a quick Popeye dance. It was very heartwarming.
1 Three Hole Punch Jim
While Popeye was undoubtedly Jim's sweetest moment of the Halloween holidays, it was not his funniest costume. That honor goes to the first Halloween costume Jim ever donned on The Office. After all, it's hard to top the first time and that's just what happens in Jim's costume from season two's "Halloween."
At first, Jim struts around the office with three black dots affixed to his shirt. He proclaims himself to be "Three Hole Punch Jim," which is a deviation from "Plain White Jim," apparently. The best moment, however, comes when one of his dots falls off and he becomes "Two Hole Punch Jim." Jim Halpert on Halloween is an undeniable godsend.
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