Even though The Office is no longer available to binge on Netflix, the show still stands as one of the most hilarious mockumentary-style TV shows in existence. A huge reason why The Office is still so beloved to this day is because its excellent cast of characters was always willing to act out hilariously cringeworthy scenes.
With Steve Carell playing the role of Michael Scott, a socially awkward manager with a desperate desire to be liked by his peers, there was really no way this show could fail. Rainn Wilson as Dwight Schrute and John Krasinski as Jim Halpert made each episode even more enjoyable. These guys, along with the rest of The Office actors, didn’t mind starring in some of the cringiest episodes of the show, and in the end, they knew that the level of comedy they were achieving would be worth it.
Here are the most cringeworthy episodes of The Office.
“Diversity Day” – Season 1, Episode 2
With the first few episodes of The Office, the show creators were pushing every possible boundary. This was especially proven in “Diversity Day,” the second episode of season one, which shines a lot of light on Michael’s childlike ignorance when it comes to racial sensitivity. When his Chris Rock routine riddled with racial slurs gets him in trouble with corporate, a third-party speaker arrives at the office to help him better understand his behavior. Instead of learning any valuable lessons, Michael decides to host his own version of a diversity seminar. He tapes labels with different ethnicities, cultures, and historical figures’ names on the foreheads of his employees for a highly inappropriate guessing game filled with plenty of cringiness.
“Prince Family Paper” – Season 5, Episode 13
Michael’s guilty conscience nearly gets the better of him in an episode titled “Prince Family Paper” from the fifth season. David Wallace enlists his help in getting information about Prince Family Paper so that Dunder Mifflin might have a better chance of squashing out the company. Some messed-up undercover work done by Michael and Dwight helps them uncover the family-owned paper business’ personal client list. Michael goes back and forth in his mind about whether or not it’s right to share the information with David after learning just how sweet and kind the Prince family really is. To make matters worse, the family even offers to fix Michael’s car after he has a minor crash in their parking lot.
“Nepotism” – Season 7, Episode 1
Starting off season seven of The Office with an episode like “Nepotism” was a bold move for the show creators, but time and time again, they proved that they knew what they were doing. There were a handful of highly cringeworthy moments to consider in this episode, but the highlight of them all came when Michael bent his super annoying nephew over Andy’s desk to spank him as a form of corporal punishment. Fortunately for Michael, his nephew didn’t return to work. Unfortunately for Michael, he ended up getting stuck with anger management classes from Toby Flenderson.
“The Chair Model” – Season 4, Episode 14
Michael’s pursuit of love never really died down until he finally moved to Colorado with Holly Flax. Before meeting her on his romantic journey, which was filled with many highs and lows, he spent a small period of time daydreaming about a chair model from a furniture magazine. It was beyond cringeworthy that he found himself falling in love with a woman he’d never met in real life, but it was even worse when Dwight revealed to him that she’d passed away in a car accident while under the influence. It got even worse when Michael forced his employees to help him meet a new girlfriend before learning about the chair model’s death. Pam regrettably set him up with her landlady and he royally offended the poor woman during their coffee date.
“Company Picnic” – Season 5, Episode 28
There was nothing more cringeworthy than watching everyone enjoy their company picnic before finding out that a group of employees there were going to be fired. That’s exactly what happened in “Company Picnic” from season five, when Michael let it slip that the Buffalo branch would be shutting down during his skit with Holly on stage. Instead of a nice ending to the company picnic, things got pretty dramatic from there.
“Michael’s Birthday” – Season 2, Episode 19
Michael is definitely an attention-seeker, and that fact was proven in “Michael’s Birthday” from the second season of the show. He was pretty unhappy that Kevin’s possible cancer diagnosis was overshadowing his birthday festivities, and while the rest of the office was worried about Kevin’s health and wellbeing, Michael was worried about his own party.
“Diwali” – Season 3, Episode 6
“Diwali” should have been an awesome celebratory episode for Kelly Kapoor and her Indian culture, but instead, Michael found a way to turn it into one of the most cringeworthy events of the series. He proposed to his girlfriend, Carol, who he barely knew at that point, in front of a huge crowd of strangers. To make matters worse, he told her it was a costume party and she showed up wearing a cheerleader uniform.
“Secret Santa” – Season 6, Episode 13
Michael prefers for things to go his way, and when things don’t, it’s very possible that he’ll throw a fit. In “Secret Santa,” he finds himself angry to learn that Phyllis gets to dress up as Santa for Christmas that year. In an attempt to rival her Santa costume, he shows up at the office dressed as none other than Jesus Christ.
“Dinner Party” – Season 4, Episode 13
The relationship between Michael and Jan was always toxic, but the toxicity of their love wasn’t put on full display until “Dinner Party.” During the episode, it becomes abundantly clear that the relationship is emotionally abusive, with Jan acting as the abuser. The cringeworthy moments flow freely throughout this episode, from Jan listening to a love song written by her former assistant Hunter to Dwight showing up with his old babysitter-turned-lover as his date. It all hits the fan when Jan shatters Michael’s miniature plasma TV with one of his Dundie Awards.
“Scott’s Tots” – Season 6, Episode 12
One of the worst things Michael probably ever did in his lifetime was promising a classroom of third graders that he would pay their college tuitions. He made a promise he couldn’t keep because he assumed that he’d be rich enough by the time the third graders reached the age of 18. At the beginning of the “Scott’s Tots” episode, Michael does his best to avoid responsibility entirely. By the end of the episode, after he’s been serenaded with a catchy rap song by the young and hopeful students, he reveals the fact that he won’t be paying their college tuition. Anyone who hasn’t seen this episode yet should know ahead of time that it’s truly as cringeworthy as it sounds.
You can watch these cringey episodes along with every other episode of The Office right now on Peacock.
