The Office is built on watching its cast live through painfully embarrassing moments, and no character better personifies the series' uncomfortable underpinnings than Michael Scott. Across his seven seasons on the show, Michael proves himself inept, quick to anger, kind of dumb, and just all around awful. Somehow, he embodies all these negative traits while still having a heart of gold.
In the most awkward Office episodes, however, Michael leans into his worst qualities without ever trying to redeem himself. While funny, these moments don’t offer viewers a sense of narrative atonement; it just looks like Michael is a bad person. Thankfully, Michael is played by Steve Carell, who loads the character with enough sweetness to make you want to binge the show until you pass out - but you may be passing out from rage.
It’s always a wedding or a party that brings out Michael Scott’s urgent need for attention. Throughout the episode, he impedes on Phyllis’s ceremony; he’s then thrown out of the reception by Bob Vance for giving a truly horrific toast.
Michael’s behavior is so abhorrent even Dwight won’t let him back in the wedding. Unfortunately, this isn’t the last wedding Michael ruins.
Not only does Michael unintentionally out Oscar as being gay in this episode, but he does so by using a bigoted epithet. Throughout the episode, his ignorance will shake you to your core, but that’s hardly the most uncomfortable part of the show.
While apologizing to Oscar in an office-wide meeting (where else?), Michael kisses him without his consent - then Dwight tries to follow suit.
After dating Pam’s mom for a few episodes, Michael books a reservation at a restaurant Pam loves for a double date with her and Jim to celebrate her mother’s birthday. While on the date, Michael realizes that at the age of 58, Pam’s mom doesn’t share his same interests - specifically, traveling and “white water rafting.”
Michael breaks up with her right there, ensuring no one in Pam’s family will ever forget her mother’s birthday.
There are few better - or more upsetting - episodes of The Office than “Dinner Party.” After ruining Jan’s scheme to sue Dunder Mifflin, Michael and Jan are completely at odds. They invite Jim, Pam, Andy, and Erin to a dinner that’s more like a tense, two-person Off-Broadway play. Over the course of the evening, it’s revealed Michael sleeps on an ottoman at the foot of Jan’s bed and he’s helping her get customers for her failing candle business.
At the end of the night, Michael and Jan get into such a big fight that she breaks his tiny TV. The cops are called and Michael goes off to stay the night with Dwight.