After multiple re-watches, you come to a simple realization: The Office is a show that is surprisingly filled with awful people. But who is the worst? For this article, I'm limiting our contestants to anybody from the original main cast. That means notable malcontents like Robert California and Nellie Bertram don't factor into consideration. That also eliminates Andy Bernard from the discussion, which is a tough call, but ultimately the right decision.
I've also decided to set aside any characters that work for corporate, as it wouldn't be fair to hold them to the same moral standards after being tainted by the corrupting power of an executive position at a mid-level paper supply chain. So goodbye to the plenty evil Jan Levinson and goodbye to any case that could be made for David Wallace, or Ryan during his corporate stint.
I've narrowed down the field to who I believe would be the top three, but I'd like to define what I mean by "the worst person" as it's a distinction that is unavoidably subjective. We can't correct for all of that subjectivity, as even our own view of the show is filtered through a narrative the documentary producers gave us. We'll do our best and try to imagine it as "the worst person according to an unseen moral observer who is not the camera crew." Think of it as the worst person through the eyes of God or through the eyes of a jury or through the eyes of that annoying owl from The Ocarina of Time, whatever works best for you. With all that said ...
The Case For Jim
Here we have our least likely, yet most likely candidate. The mainstream Office fan recognizes Jim as not only the grounding force of the show but as the platonic ideal for the modern man. Every other Hinge profile reads, "just a Pam looking for her Jim," and, yet, I dare to label this witty, well-spoken, compassionate man as a bad guy? Well, I wish I could take the credit for this, but that Jim is an asshole isn't even that new of a take.
First of all, Jim takes pranking Dwight to sociopathic levels. At first, Jim's pranks seemed somewhat reasonable as some sort of slight always justified them, and what's the real harm putting a stapler inside of some jello? But eventually, those slights became flimsier, and the pranks became much harsher.
There are also Jim's perplexing relationships with women. He takes Amy Adam's character on the office booze cruise, only to callously dump her with a single word. Then, in season 3, he strings Rashida Jones' character on for months, letting her follow him to Scranton and again unceremoniously dumps her in favor of Pam. And of course, most famously, he pursued Pam in seasons 1 and 2 while she was still engaged. I'm not saying that you're not allowed to dump someone or that you shouldn't follow your heart, but damn, Jim, you crushed Amy Adams' heart like Dwight falling through wrapping paper.
Even with Pam, Jim has trouble thinking outside himself. It's why in the later seasons, he bought a house without consulting her, invested $10,000 in a sports company without consulting her, and then told everyone in the office he was leaving to go to Philly without consulting her. This is a bad enough husband move, but considering they have a child at this point, it's damn near unforgivable.
The Case For Angela
If we're going to give Jim shit for pursuing Pam while she was engaged and stringing people along, then we have to give Angela (and Dwight) shit for carrying on an affair while she was engaged to Andy. There are a few reasons why I nominate Angela over Dwight, but the main one is I feel Angela's actions carry more intention. Dwight is the George Bush to Angela's Dick Cheney. He might be misguided, but Angela's prime directive is evil.
Take, for example, in the episode "Business Ethics," where Angela reveals that she once reported Oscar to immigration. Or consider how as head of The Party Planning Committee, she lords whatever little power she has over others. When Pam suggests decorating in orange for "Benihana Christmas," Angela quickly shuts her down, saying, "orange is whorish."
Angela is flat-out mean, and even once admitted, "I normally don't enjoy making people laugh." What she does enjoy, though, is the displeasure of others, and it's why you can see her give a rare, agreeable nod upon allowing Andy and Dwight to duel over her. It is later revealed that she has been the object of affection of, not one, but two sets of men choosing to duel over her.
Does Angela have redeeming qualities? I guess she does in the way that a sack of excrement could be used as beet manure. Angela does soften up as the series goes on, and there at times seems to be genuine respect between her and Oscar. However, her treatment of certain characters like Pam, Phyllis, Andy, and sometimes even Dwight, makes her a horrible person even amongst the lowly standards of a TV sitcom.
The Case For Toby
Surely Michael would claim that Toby is the worst, and has done so in about every episode, but the TV narrative is that Toby is a swell guy. He's the HR rep, and as such, functions as a foil to Michael and his many PC blunders. But Toby's effectiveness as an HR rep is only surface level because, in reality, Toby takes a sloppy shit all over the HR mattress in any of the ways that actually matter.
For starters, Toby outs Oscar for being gay in "Gay Witch Hunt." Michael takes the heat for this, but it's Toby who's the one that tells Michael, and considering that Toby acknowledges how deeply personal a moment coming out is supposed to be, you'd think he'd be more sensitive about spreading that information.
Toby also has a weird thing with race. He buys a "Princess Unicorn" for his daughter last minute (minus points for bad parenting as well) and is visibly disappointed to see that the doll is black.
Later, in season 6, Toby drives by Darryl's home and confusing his sister Gwyneth for him, shouts out, "asshole!" It's not becoming of an HR rep to ever shout obscenities at employees of a company, but it's also not a great look that he misgenders a black woman.
But Toby's most egregious offense has to be how creepy he is towards Pam. He hounds her to get a photo between the two of them during the episode "Goodbye Toby," and in the episode "Night Out," he puts his hand on Pam's knee. Again, Toby's the HR rep. He's supposed to be defending against that type of behavior. It's like if a food inspector went around a restaurant and pissed in the deep fryers.
Roy - He almost assaults Jim and smashes a bar to pieces. He was also a lousy fiance for Pam. Again, he'd also be higher, but Roy's transgressions are all id and out in the open. To me, "the worst person' is someone who's more secretly insidious like my big three.
Michael -Finally, we have the star of the show. Michael is the worst boss imaginable (at least according to NBC's AGENDA!) and, on paper, might also be "the worst person." But he's also so naive and congenial in nature that it's hard to judge him too harshly. Meanwhile, Toby, Jim, and Angela all know when they're being dicks.
And as Who Is The Worst: The Office Edition comes to a close: My personal feeling is that Michael got it right from the beginning. Toby is the worst; it just took ten years of intense scrutiny for me to see it.
Support Dan on Twitter and he will talk about his life with you in lieu of getting a therapist.
Top Image: The Office