The British series that NBC’s The Office was based on relied heavily on cringe humor, so the writers of the American remake brought that sensibility across the Atlantic. There are certain episodes of The Office that are so cringeworthy — usually courtesy of the master of social awkwardness, Michael Scott — that fans with a weak stomach will skip them on rewatches; they just can’t stand the cringe.
But to other fans, the cringe-filled installments are the show’s best because the actors revel in it brilliantly, and these fans intentionally seek out the cringe. So, here are the 10 cringiest episodes of The Office, ranked.
Nepotism (Season 7, Episode 1)
In the Season 7 premiere “Nepotism,” everyone in the office encourages Michael to fire the new intern, Luke (played brilliantly as an unbearable jerk by guest star Evan Peters). Michael is reluctant to fire Luke, and it’s later revealed that he’s Luke’s uncle.
The episode finds its peak of cringe as Luke interrupts a meeting in the conference room and he ignores Michael until Michael snaps, bends him over Andy’s desk, and spanks him.
Garden Party (Season 8, Episode 4)
Andy puts on the titular event in Season 8’s “Garden Party” entirely to impress his difficult-to-please father. Andy's younger brother (and his parents’ favorite child) threw his own garden party and shared a duet with his dad, and a video of it went viral online — to which Andy did little to hide his jealousy.
When Andy’s parents arrive at his garden party — a shallow attempt to replicate his brother’s party and earn their approval — they’re just stopping by on their way to see Moneyball. And when Andy tries to organize a father-son duet, his dad shuts him down, takes his guitar, and hijacks the performance.
Secret Santa (Season 6, Episode 13)
When Michael doesn’t get his way, he has a tendency to ruin everybody’s fun. He’s the office Santa every year, but one year, Phyllis wants to be the Santa, and Jim — back when he was the co-manager of the Scranton branch — is happy to let her.
Michael, on the other hand, isn’t happy, and spends the rest of the episode as Jesus, using the karaoke microphone to step on Phyllis’ short-lived career as Santa.
Diversity Day (Season 1, Episode 2)
In the second ever episode of The Office, a speaker is brought in to talk to the Scranton branch about diversity as a corporate response to Michael reciting a slur-ridden Chris Rock routine verbatim to his employees.
Michael interrupts and ignores the speaker until he finally loses patience and leaves, at which point he decides to put on his own diversity seminar. The cringiest moment in the episode is Michael yelling, “Try my cookie-cookie!” at Kelly in an Indian accent until she slaps him across the face.
Diwali (Season 3, Episode 6)
Season 3’s “Diwali” has a quick succession of two of The Office’s cringiest moments. After meeting a couple at Kelly’s Diwali celebration who only met once before getting married, Michael is inspired to propose to Carol — who is dressed as a cheerleader, because Michael told her it was a costume party — after just a handful of dates, in front of the whole party.
After she turns down his proposal, Michael is comforted by Pam, and drastically misreads the situation and leans in to kiss her.
Prince Family Paper (Season 5, Episode 13)
David Wallace sends Michael and Dwight to get some information about a local family-owned paper business’ client base, because they’re not a public company and therefore, he can’t get a report on them. Michael pretends to be a lawyer and gets a list of their clients while Dwight pretends to be a salesman looking for a job and learns their sales strategy.
The family turn out to be the nicest people ever, and they even fix Michael’s car when he crashes it in the parking lot. Watching this episode is so uncomfortable because of Michael and Dwight’s true motives. It’s later revealed in the episode “Two Weeks” that Dunder Mifflin succeeded in running the Prince family out of business.
Gay Witch Hunt (Season 3, Episode 1)
In the Season 3 premiere “Gay Witch Hunt,” Oscar was outed as gay to the office when Michael used a homophobic slur against him without realizing it was a slur. Throughout the episode, Michael tries to prove to Oscar that he’s okay with his sexuality, but of course, he just makes things worse.
The cringiest moment in this episode is Michael awkwardly kissing Oscar in front of all his co-workers in the conference room and then, with a tear in his eye, saying, “I did it.”
Phyllis’ Wedding (Season 3, Episode 16)
When Phyllis married Bob Vance of Vance Refrigeration, she put Michael in the wedding party just so he’d let her have six weeks off for her honeymoon. Naturally, Michael made the whole day about himself. He pushed Phyllis’ dad down the aisle, and when he stood out of his wheelchair to walk her up to the altar, inspiring everyone in attendance, Michael turned to the camera and said, “This is bullsh*t.”
He also prematurely announced the couple as husband and wife in the middle of the ceremony, gave a long, unwieldy speech until Bob finally had to take the mic from him, and made himself a third wheel when the newlyweds were cutting the cake.
Dinner Party (Season 4, Episode 13)
Widely regarded to be the best episode of the entire series, “Dinner Party” sees Michael and Jan hosting Jim and Pam, Andy and Angela, and later Dwight and his old babysitter at their condo.
From Michael asking Jim and Andy to invest in Jan’s candle business to Jan thinking Pam is secretly in love with Michael to a tour of the house revealing a video camera set up in the bedroom, “Dinner Party” is filled with insufferably cringeworthy moments that dare you to look away.
Scott’s Tots (Season 6, Episode 12)
Without a doubt, Season 6’s “Scott’s Tots” is the cringiest episode of The Office. A class of third-graders that Michael pledged to put through college when he assumed he’d become a millionaire are now about to graduate, and he has to go down to the school and tell them that he won’t be able to pay for their education. Pam makes Erin go with Michael to ensure that he tells the truth.
Upon arrival at the school, Michael is praised with a catchy song and some inspirational speeches, and then he has to stand in front of the kids and deliver the bad news. Instead of college education, he offers them laptop batteries. It goes about as horribly as one would expect.