The Office stands out as one of the best sitcoms of all time, but there are a handful of episodes that were genuinely uncomfortable to watch. Michael Scott and the rest of the team at Dunder Mifflin came together to create one of the funniest shows in The Office. From the very beginning in 2005, the show took a concept from a British sitcom of the same name by Ricky Gervais, and positioned it in an American setting with a whole new cast, and while some regional adaptations don't hit the mark, this one really hit the mark.

In large part, this was down to the incredible casting, with standout performances from Steve Carell, John Krasinski, and Rainn Wilson from season 1 onwards. But even the ing cast added essential layers to the show that took the quality to new heights with incredible chemistry and an authentic sense of people thrown together in an office. However, the show did have some moments that failed to resonate, either due to being so awkward and tense, or making beloved characters into something unrecognizable.

8 Gay Witch Hunt

The Office Season 3, Episode 1

Early in the show's run, there were moments when Michael Scott majorly crossed the line from quirky, silly boss man, to actually harassing employees. While he was always prone to throwing out inappropriate jokes, and he failed to see when his words made others feel uncomfortable, things were taken to another level in "Gay Witch Hunt." As Michael so often does, he made inappropriate remarks, and instead of apologizing and moving on, he made things a lot worse.

After Michael uses an offensive homosexual slur towards Oscar, Toby, as the HR rep, advises Michael not to do so again. Of course, Michael is reluctant to follow any of Toby's advice, but when he learns Oscar is actually gay, and is upset by Michael's use of the word, Michael tries to make amends in his own way. But unfortunately, this leads to Michael forcing Oscar to come out to his colleagues against his will, and Michael tries to kiss him, thus increasing the intensity of the harassment.

7 Moving On

The Office Season 9, Episode 16

The last season of The Office had some bright spots, but one of the biggest betrayals of the show also came with the fall of Andy Bernard. Andy was always a goofball, but in the final season of The Office, he was an outright jerk. This is particularly clear when, after abandoning the team for an extended period to have a secret vacation from work (while still being paid), Andy returns to find out his ex-girlfriend, Erin, is dating one of the new hires, Pete.

The entire episode is a hard watch, as the best of the cast are at their worst.

In an extra petty move, Andy hires both Erin and Pete's exes to work at Dunder Mifflin out of spite. Adding further to the awkwardness, there is a subplot where everyone's favorite couple, Jim and Pam, are at odds when Jim's aspirations to move to Philadelphia conflict with his wife's goals. The entire episode is a hard watch, as the best of the cast are at their worst.

6 The Duel

The Office Season 5, Episode 12

About halfway through the show's run, Any experienced even more bad luck when his fiancée, Angela, was cheating on him for months with Dwight. Dwight and Angela's affair was a huge betrayal, with Angela leading him on and Andy being made a complete fool. However, things got infinitely worse when the entire office caught wind of the affair, and Andy was left as the last person to find out.

Michael was the one to bite the bullet and reveal the truth, though he did so while driving away to avoid the ensuing drama. Then, when Andy confronts Dwight and Angela, instead of being remorseful or feeling ashamed, Dwight challenges Andy to a duel, much to Angela's delight. This horrific scene plays out with a positive ending, but the ordeal that leads to that outcome is painful to endure.

5 The Convict

The Office Season 3, Episode 9

While some of the most awkward and cringey episodes in The Office have a rare few funny moments to carry the audience through, "The Convict" is one of the rare few that is both hilarious and deeply problematic. In an effort to build team unity, Michael looks to the team for advice and guidance on what they can do. When Angela sarcastically implies that she s helping criminals, Michael runs with the idea, and Prison Mike is born.

As Michael delivers a presentation to the group, attempting to build morale and unity in the office, he switches to a character he has called Prison Mike. Prison Mike is more aggressive, rude, and problematic than Michael, and the baseline was already not at an appropriate level. The result is an awkward battery of weird activities that Prison Mike forces on the employees in one of the wackiest and most unusual displays from the quirky Michael Scott.

4 Sexual Harassment

The Office Season 2, Episode 2

As is suggested by the name, this episode is built on a foundation that is grounded in awkward and uncomfortable subject matter. This episode, early in the show's run, leans heavily into the source material of the British show that inspired it, and after Todd Packer made numerous appearances by phone in season 1, he makes his on-screen debut here. And as becomes clear very quickly, Packer is not a good guy.

Unfortunately, Michael adores Packer, and believes he is one of the funniest, most successful, and suave individuals he has ever met. This leads to Todd Packer bullying Michael, and influencing him to participate in numerous inappropriate actions. This episode crosses the line at several points, and it's just a generally uncomfortable outing that did not live up to the standards the show was capable of.

3 Todd Packer

The Office Season 7, Episode 17

Fortunately, Michael does learn his lesson with Todd, but it takes a long time. In fact, it isn't until season 7, when Todd asks a favor of Michael to give him a cushy desk job rather than keeping him as a travelling salesman, that Michael sees Todd's true colors. Todd res the office, and everyone is less than enthusiastic about his presence there.

However, Michael is naively excited, and cant wait for his girlfriend, Holly Flax, to meet the man he considers to be his best friend.

But when Todd arrives, he is his typical self, who is a complete jerk. Todd belittles others, and constantly makes people feel uncomfortable. Holly tells Michael to get him under control because he is causing problems, and when Todd makes a nasty comment about Holly, Michael has had enough. Todd leaves, and it's a happy ending, but his presence throughout the episode made things incredibly uncomfortable.

2 Scott's Tots

The Office Season 6, Episode 12

A legendary episode of The Office, "Scott's Tots," is infamous for being deeply uncomfortable. The episode reveals that when Michael was early on in his career, he found himself deeply moved by a group of young students who were in a less privileged area. As a gesture of kindness, and convinced that he would eventually be a millionaire, Michael promised to pay for these kids' college educations if they studied hard and stayed in school.

However, Michael's dreams of wealth did not come to fruition, and as a result, he had the monumental task of informing the kids that he couldn't deliver on his promise. The entire episode is deeply uncomfortable, and while Michael was acting out of a place of love and hope, he destroyed these kids' faith in him. There were again positives to come out of the episode, but it's not an easy watch.

1 Dinner Party

The Office Season 4, Episode 13

Finally, one of the most disturbing and insane episodes ever to come out of The Office, "Dinner Party" was a wild ride as Michael and Jan invite Jim and Pam over for dinner. Jan worked as Michael's boss from the start of the show, but the pair eventually sparked up a romantic relationship. Then, when Jan got fired, she also got really weird.

Jan is abusive towards Michael, belittling him, and clearly displaying interest in other men in front of him. This is made all the more uncomfortable as Jim and Pam, a happy, healthy couple, are forced to watch their boss and his ex-boss in an incredibly toxic relationship. It's so uncomfortable, and Jan is incredibly creepy throughout. However, it does highlight the incredible and versatile talent of the actors involved in The Office to make such a creepy storyline work.