The Most Cringeworthy Episodes of The Office

Comedy Lists The Office
Share Tweet Submit Pin
The Most Cringeworthy Episodes of <i>The Office</i>

Despite what everyone’s dating app profile will tell you, liking The Office is not a personality. Nor is hating it, of course. People love to jump on any chance they get to quote the show or tell you why you’re an idiot for liking it. It’s almost like you can’t get to 200 episodes without annoying the hell out of a lot of people. While the sitcom is too prominent in the zeitgeist to call it polarizing, the show’s many detractors have a very common gripe with it, one that this fan cannot fault them for.

The show has often been criticized for being too cringey. Imbued with dry humor throughout and led by an irritating moron of a character, the show has a penchant for playing off uncomfortable moments for comedy. When done well, like season four’s “Dinner Party,” the uncomfortableness is lifted to a level of absurdity and foolishness that soothes over the awkwardness. When done poorly, though, it’s just nauseating, with one particular episode earning an infamous reputation for being unwatchable.

The Office got a lot right, earning it multiple binge watches. However, there’s still a few episodes we’d rather skip than sit through again.

Pilot (Season 1)

the_office_cringe_pilot.JPG

More often than not, the pilot is the least favorite episode of a TV series. They are tasked with establishing a new world before all the pieces are fully in place. The first episode of The Office isn’t that especially high on the cringe meter but it’s certainly not entertaining in the least. Every character but Michael Scott is trying their hardest to do the least, which honestly describes the entire hard to watch first season. However, unlike later episodes, the pilot is more irritating than it is boring. Following its British predecessor, the show’s humor is so dry it shrivels up the fun with many of the jokes actually just textbook examples of sexual harassment. The episode provides exactly one laugh, the infamous stapler in jello moment, in between Michael doing a million sad uncle bits that are more eye-roll inducing than goofy. In the first two episodes, Michael gets slapped and tearfully called a jerk by his employees and both are justifiable responses which go against the spirit of the show we’d later come to love. Instead of elevating the relatable work culture quirks and drawing out the absurdity that lies within the day-to-day mundanity of an office, it feels more like a crash course experience of what it’s like at a run-of-the-mill terrible job. Even ugly characters have to be somewhat likeable and the Michael on display here isn’t.


“Michael’s Birthday” (Season 2)

the_office_cringe_birthday.JPG

Many sitcoms have punching bag characters that are never allowed to win, but that tension has to be eased every once in a while for audience’s sake (and to prevent the writing from being too predictable). In season two, Michael’s misfortunes go from punching bag to beating a dead horse. A lot of Michael’s awfulness as a person and as a boss comes from a place of naivety and a lack of self-awareness. He’s more pitiful than outright ghoulish which makes “Michael’s Birthday’’ cross the line of schadenfreude territory into just a sad viewing experience. Watching him try so incredibly hard to make his birthday special and press his coworkers to feign even an ounce of care feels cruel. The sublot of Kevin’s looming skin cancer diagnosis is supposed to throw a wrench in the festivities (Angela goes so far as to tell Michael directly, “Nobody cares about your birthday”) but it’s clear that The Office’s disinterest would still be there without it. Even in a fictional world, it’s hard to see someone’s birthday, of all days, be a showcase of loneliness.


“The Chair Model” (Season 4)

the_office_cringe_chair_model.JPG

One of, if not the best, episodes of the entire series is followed by an easily skippable one. While not the most painful, the third act of “Chair Model” features a scene that’s too uncomfortable even for a comedy. Following Michael and Jan’s fallout from “Dinner Party,” Michael enlists The Office in a matchmaking campaign to find him a rebound. Naturally, this leads to a lot of insensitive remarks about women from Michael which culminates in one of the worst blind dates ever captured on film. Watching Michael treat Pam’s landlady like some undesirable mess is not worth watching and him treating her like she’s wildly beneath him is one of the most damning things he’s done on the show. I can’t even call it an awkward interaction, it’s just mean.


“Christening” (Season 7)

the_office_cringe_christening.JPG

For some reason (it’s stated in the episode but isn’t remotely satisfying), the entire office attends the christening of Jim and Pam’s baby. Nobody’s personality traits are highlighted (except for Angela) as everyone exists as one collective blob. It’s boring, and yes, very cringe. Why are they there? “Well, it’s a TV show, girl,” but no, seriously, why! Even by TV measures, it makes no sense these work acquaintances would get together on a weekend morning to go to a church none of them are members of. They clearly do not want to be there and neither do I. Everybody, church members and Dunder Mifflin staff, are extra awful this morning and despite a scolding speech from Michael, any message the writers thought they were making by having the outcast point out their flaws just falls flat (and is kinda undone later on). None of the jokes really land nor are they particularly prominent (Dwight’s attempt to sell paper during church service was better done by the “Mr. Plow” episode of The Simpsons). It’s just 30 minutes of people being nasty in an uninteresting way. Making fun of church is nothing new, it’s pretty easy fodder in fact, but everybody’s presence feels like an incursion rather than a creative critique. We don’t see much of the main cast’s lives outside of The Office and this one felt unnecessary and uncharacteristic of the group (whereas “Viewing Party” actually does this well). There’s just no joy to be gleaned from these all bark and no bite 30 minutes of TV and it doesn’t feel like it was made with any. Skip it and spend one minute on Nextdoor if you want the experience.

But none of these episodes can hold a putrid candle to…


“Scott’s Tots” (Season 6)

the_office_cringe_scotts_tots.JPG

Why? Why was this made? Why was this done to us? Six seasons into what had been cemented as one of the most popular sitcoms ever and they drop an episode so unwatchable it’s become the stuff memes are made of. It’s one thing for Michael to fail to deliver on meager promises made to his coworkers; it’s another to watch him force his delusions of grandeur onto a room of POC grade school students whose college tuition he stupidly promised to pay for. It goes beyond second hand embarrassment and into second hand nausea. It doesn’t play with tension, it suffocates you with it. It’s a skin crawling episode so overbearing in it’s cringeyness that no B story can make a lot of people watch it again.


Olivia Cathcart is a comedian and writer.

Also in Comedy