Nobody does cringe humor better than the US version of The Office. Whether it's Michael Scott making a fool out of himself in front of an entire crowd or Kelly Kapoor trying a tad too hard to impress Ryan, this show is absolutely loaded with moments that are bound to make you uncomfortable (but in the best way imaginable).
Most of us can't get enough of these hilariously awkward moments from the show, and in a way, they remind us of exaggerated versions of our own lives. So without further ado, these are the 10 most cringe-worthy moments on the entire series! Warning: You will cringe. Hard.
10 KEVIN SPILLS HIS CHILI EVERYWHERE
One of the most cringeworthy moments on the entire show is also one of the most hilarious moments. Kevin Malone may not be the brightest bulb in the shed, but he sure can make the best chili recipes. The Malone's have had the same famous chili recipe for generations, and Kevin is prepared to bring an entire pot to work.
He manages to carry it up the stairs and is about to share it with the whole office until he spills the whole pot everywhere until he's practically drowning in chili. It is definitely hard to watch, but it is beyond hilarious none the less.
9 KELLY FAKES A PREGNANCY TO KEEP RYAN AROUND
This scene proves just how skilled Mindy Kailing is when it comes to comedic timing. Not only is Kailing one of the head writers on The Office, but she also plays one of the most hilarious characters in the series to date.
Ryan and Kelly have always had an extremely dysfunctional relationship, and their dynamic is easily one of the funniest to watch. They are constantly arguing and being terrible to one another, yet Kelly faking her own pregnancy takes the cake as one of the most cringe-worthy moments.
8 THE ENTIRE "DINNER PARTY" EPISODE
How could we not include "Dinner Party" on this list for most cringe-worthy moments on the show? Jim put it best when he suggested Michael and Jan were playing their own game of who can make their guests the most uncomfortable.
It just proved how awful and dysfunctional Michael and Jan's relationship was, and the cherry on top of it all was when Jan blasted her old assistant Howard's music as she tried to sensually dance with Jim. It was just a total disaster to witness, yet we couldn't seem to look away!
7 EVERY INTERACTION WITH MICHAEL AND OSCAR
One of the most underrated and hilarious relationship dynamics on the show is the unusual bond between Michael and Oscar. It was a strange relationship from the very beginning, dating back to the "Diversity Day" episode when Michael asked Oscar, "Is there a term besides Mexican that you'd prefer?" Could their dynamic possibly get any more cringy?
Unfortunately, the answer is yes. In another episode, Michael wants to prove his loyalty to Oscar so he kisses him on the mouth in front of the entire office. Just thinking about all that awkwardness makes us clench up!
6 MICHAEL AT IMPROV CLASS
Anyone who has ever taken an improv class before knows that one student who is just like Michael Scott. The student who hogs the entire scene and always ends up playing the same obnoxious role over and over again. In improv class, Michael always plays an FBI agent who kills every person in the scene.
He keeps doing this bit repeatedly and no one in the class can stand him. The class gets so fed up with Michael that they don't include him in their plans.
5 JIM AND CHARLES MINER GET OFF ON THE WRONG FOOT
In season 5, Idris Elba comes onto the show to portray Charles Miner, the strict new boss who is basically the opposite of Michael Scott. While Michael was manager, Jim was able to goof around and pull elaborate pranks with Pam as much as possible, yet Elba's character had a totally different idea about how to properly run a workplace.
He instantly disliked Jim, who he deemed as lazy and juvenile. Their entire dynamic was super hard to watch because it was such a heavy transition in comparison to Jim and Michael's relationship.
4 MICHAEL SPEAKS AT RYAN'S BUSINESS CLASS
An unforgettable episode on the show was when Michael went to give a speech at Ryan's business class. We all know how much Michael looks up to Ryan and places him on a pedestal, so he was unimaginably thrilled when Ryan asked him to do this. It was a mandatory assignment that Ryan was secretly dreading, while Michael, on the other hand, was bursting with joy over this opportunity.
He ended up making a fool out of himself during the speech, and he ripped out a student's very expensive textbook pages because he said, "books teach you nothing." It was just all-around hilarious and even more so cringy.
3 THE ENTIRETY OF PHYLLIS'S WEDDING
Phyllis's entire wedding was an absolute cringe-fest from start to finish. For one thing, she kept stealing all of Pam's ideas for her wedding with Roy. Another extremely cringe-worthy aspect was the fact that Kelly wore white to the wedding. Yet one of the cringiest moments by far was Michael Scott's role in the entire wedding when he acted as though Phyllis's special day was actually his special day.
He was so excited to wheel Phyllis's father down the aisle and he kept inappropriately barging into the intimate moments shared between the newlyweds. Let us also not forget when Dwight assumed Phyllis's uncle with dementia was crashing the wedding and he kicked him out onto the street.
2 TOBY GETS A LITTLE TOO FLIRTY WITH PAM
Toby's weird obsession with Pam never seemed to fade away throughout the series, even when the entire office knew she was with Jim. In one scene, the employees at Dunder Mifflin are hanging out together and Toby puts his hand on pam's knee and starts to rub it in an affectionate way.
Everyone watches this encounter in a mixture of shock and horror, and Toby who realizes his mistake quickly announces that he's going to be moving to Costa Rica. This is followed by him running off in horror and jumping the fence. It was easily one of the most awkward encounters on the entire show.
1 SCOTT'S TOTS
And finally, we had to include Scott's Tots on the list as one of the most cringe-worthy moments on the show. Ten years ago from the episode, Michael promised a bunch of third graders that if they were willing to graduate high school, he was willing to pay for their college tuition. He assumed that in ten years from when he made the claim he would be filthy rich and able to afford the payment.
Spoiler alert: he couldn't. He ended up letting down all of those kids who were so excited, telling them that he was unable to make their dreams come true. The entire episode was super cringe-worthy, especially when all the kids did a song and dance for Michael because they were so thrilled. It was quite possibly the hardest episode to watch without cringing throughout the entire thing.
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