The Office’s most uncomfortable episodes recapture the cringe humor of the original British show. Season 4, episode 13, “Dinner Party,” perfectly encapsulates what it’s like to spend a tense evening with a toxic couple constantly sniping at each other. It might be tough to watch, but it’s a masterpiece nonetheless.
But there are some episodes of The Office that are excruciating to sit through, like when Michael made Phyllis’ wedding all about himself. There’s an entire half-hour episode of brazenly objectifying Hilary Swank. There’s an episode where Jim and Pam get into a bitter argument that ends in tears. The Office is a great show, with plenty of really great episodes, but it doesn’t have a perfect track record.
5 Prince Family Paper
Season 5, Episode 13
Michael and Dwight con a local business run by a sweet, loving family in season 5’s “Prince Family Paper.” Under the guise of a harmless business meeting, they get their hands on the Prince family’s entire client list, with the ulterior motive to poach their customers. A few episodes later, it’s revealed that Michael and Dwight’s antics ultimately put Prince Family Paper out of business. It’s horrible to see this adorable, unsuspecting family get destroyed.
But the B-plot in “Prince Family Paper” is painful for a totally different reason.
Usually, in an episode with such an agonizing A-plot, the B-plot provides some much-needed respite. But the B-plot in “Prince Family Paper” is painful for a totally different reason. It sees the entire office debating whether or not Hilary Swank is hot. Not only is it not very funny; it’s uncomfortable to see a real person objectified for an entire episode.
4 Customer Loyalty
Season 9, Episode 12
Season 9’s “Customer Loyalty” introduced one of The Office’s most hated characters: Brian the boom operator. Brian steps on camera to console Pam when she breaks down crying after a heated argument with Jim. This whole final-season storyline of a rough patch in Jim and Pam’s marriage was difficult to get through — especially since the early seasons were built on their love story coming together — but that difficulty peaked in “Customer Loyalty.”
It seemed really out of character for Jim to lash out at Pam for something as trivial as filming a school performance he should’ve been at. The needless marital melodrama felt more like a soap opera than a sitcom. And Brian’s introduction made the show way too meta.
3 Phyllis' Wedding
Season 3, Episode 16
Michael never has much social awareness, and his behavior is often beyond the pale, but even by his standards, he acts like a petulant jerk at Phyllis’ wedding. At every single turn, Michael makes Phyllis and Bob’s wedding all about him. He makes a scene partway down the aisle, he prematurely announces them man and wife in the middle of the ceremony, and he gives a long, meandering, wildly offensive speech that has to be cut off by force.
Wedding episodes are usually the most feel-good installments of a sitcom; they’re a celebration of love on the happiest day of a popular character’s life.
But “Phyllis’ Wedding” is really tough to sit through, because Michael can’t just yield the spotlight to the bride and groom. Plus, it’s hard to watch Pam make the misguided decision to get back with Roy.
2 Vandalism
Season 9, Episode 14
Brian the boom operator came back in season 9’s “Vandalism,” but that’s not what makes the episode so difficult to watch. The Office’s final season finally brought back Pam’s artistic ambitions as Nellie commissioned her to paint a mural in the warehouse. But things took a dark turn when one of the warehouse workers, Frank, defaced the mural.
Pam’s investigation into the vandalism is a lot of fun — and brings back fan-favorite Nate — and Pam and Dwight’s revenge, vandalizing Frank’s truck, is satisfying to see. But in the episode’s final moments, Frank confronts Pam in the parking lot and tries to violently attack her before being stopped by Brian. The Office is usually a comfort show, but it’s actually scary to see Pam being physically threatened.
1 Scott's Tots
Season 6, Episode 12
Easily the hardest episode of The Office to watch — and one that a lot of people skip on rewatches — is season 6, episode 12, “Scott’s Tots.” The term “cringe humor” doesn’t even begin to describe how painful “Scott’s Tots” is. The episode reveals that Michael promised to pay for an entire third-grade class’ college tuition, and now, they’re all about to graduate and he has to stand in front of them and tell them he can’t afford to keep his promise.
The genius of this premise is that Michael did something awful, but he had good intentions.
But unlike some of the other entries on this list, “Scott’s Tots” is difficult to watch in the best way. The genius of this premise is that Michael did something awful, but he had good intentions. The Office’s most excruciating episode is a masterpiece of cringe comedy.
The Office
- Release Date
- 2005 - 2013-00-00
- Network
- NBC
- Showrunner
- Greg Daniels
Cast
Michael Scott
Dwight Schrute
WHERE TO WATCH
- Directors
- Greg Daniels, Paul Lieberstein, Paul Feig, Randall Einhorn, Ken Kwapis
- Writers
- Ricky Gervais, Greg Daniels, B.J. Novak
- Franchise(s)
- The Office
- Creator(s)
- Greg Daniels
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