The Office's Most Cringe-Worthy Episodes, Ranked

John Krasinski as Jim on The Office
(Image credit: NBC)

I’m not sure I can think of a TV show that’s made me cringe more than The Office. The workplace comedy, which is now one of the shows on NBC’s Peacock streaming service, excels at creating moments that are so hard to watch, you might have to cover your eyes. 

Most of these excruciating moments are thanks to Michael Scott (played by Minions: The Rise of Gru actor Steve Carell), the well-meaning but misguided boss of Dunder Mifflin’s Scranton branch. While the regional manager has some moments of brilliance that suggest he’s actually a good boss, those are outweighed by moments of sheer insanity.

Here are the top 10 episodes from the NBC show that were so cringey they were actually painful to watch.

Michael (Steve Carell) dressed up as "Prison Mike:

(Image credit: NBC)

10. “The Convict” (Season 3, Episode 9)

After learning that one of his new employees, Martin, is a former white-collar criminal, Michael decides to demonstrate the harsh realities of prison to his staff via one of his many personas: Prison Mike.

In an effort to convince everyone that Martin’s time in prison wasn’t better than working at Dunder Mifflin, Michael puts on a bandana and begins a “scared-straight” style presentation in the conference room. Michael obviously doesn’t know anything about prison though, so Prison Mike includes details like “gruel sandwiches” and Dementors (yeah, like the ones from the Harry Potter movies).

The presentation ends with Michael locking all of his employees in the conference room so they can “experience prison.” Martin obviously quits, because he found the entire situation as absurd and uncomfortable as we do.

Steve Carell as Michael Scott on The Office

(Image credit: NBC)

9. “Take Your Daughter To Work Day” (Season 2, Episode 18)

To entertain the kids on Take Your Daughter to Work Day, Michael busts out a VHS tape of his time on the local children’s program, Fundle Bundle. Little Michael’s segment with a puppet named Edward R. Meow ends up making everyone in the room uncomfortable, especially this comment about what he wants to be when he grows up:

I want to be married and have a hundred kids so I can have a hundred friends, and no one can say no to being my friend.

The look on the puppet’s face says it all.

The cringe-worthy episode also includes an outraged Stanley yelling at Ryan for talking to his daughter, as well as Michael’s creation of an online dating account with the unfortunate name “Little Kid Lover.” This episode definitely makes the list.

Andy (Ed Helms) and his fellow cast members in Sweeney Todd

(Image credit: NBC)

8. “Andy’s Play” (Season 7, Episode 3)

As if Andy’s constant singing isn’t cringey enough, his performance in a local production of Sweeney Todd takes the cake for Andy’s most unbearable moment and one of the most uncomfortable episodes of all time.

After forgetting to silence his phone before going onstage, Andy (Ed Helms) checks his notifications in the middle of the scene and attempts to go off-book to repair his mistake. He ruins the scene, committing a major slip-up when he calls Sweeney Todd a murderer, something his character wouldn’t have known.

To make matters worse, Michael has a vendetta against the actor playing Sweeney Todd since he himself tried out for the role with a monologue of an entire episode of Law & Order. Michael also lets a wine bottle roll loudly across the theater floor and accidentally pops a bunch of balloons, both of which interrupt the performance. For the cherry on top, Michael loudly boos Sweeney Todd during the curtain call.

Dwight (Rainn Wilson) and Michael (Steve Carell) stake out a rival paper company in their car

(Image credit: NBC)

7. “Prince Family Paper” (Season 5, Episode 13)

This painful episode centers around Michael and Dwight’s plan to take down a rival paper company from the inside. With Michael posing as a potential client and Dwight (Rainn Wilson) posing as a man looking for a job, the two spend time with the Prince family to get top-secret information about their business operations.

The plan goes well, and the pair leave with a list of Prince Family Paper’s clients—but while leaving the parking lot (in the same car, despite stating earlier that they were strangers), Michael damages his car, preventing a smooth getaway.

The entire Prince family bands together to help Michael and Dwight fix their car, causing Michael to feel guilty about possibly ruining the family’s business. He gives the client list to David Wallace anyway, calling the moment “bittersweet” (bitter because he ruined the nice family’s life, and sweet because his boss was happy with him).

Meanwhile, the rest of the office debates whether or not Hilary Swank is hot, which, if you can believe it, is the least cringey part of this entire mortifying episode.

Michael (Steve Carell) with a band-aid over his cold sore

(Image credit: NBC)

6. “Sex Ed” (Season 7, Episode 4)

In this Season 7 episode, Michael learns that what he believes to be a cold sore on his lip is actually a form of herpes. Without receiving a diagnosis from a doctor, Michael begins the daunting task of calling all his former lovers to let them know he has an STD. First up is Donna, and Michael reveals the name of his STD by spelling it out for her: H…I…R…P…E…E…S.

All of Michael’s past girlfriends have choice words for him, but the most awkward of these encounters occurs when he visits Jan, his former girlfriend and boss, whose young daughter is in the room when Michael spills the news. The only thing that could have made this episode more uncomfortable would be if Michael actually had herpes (he doesn't. It's an ingrown hair).

Andy also holds a sex education seminar, where he demonstrates how to put a condom on a pencil.

John Krasinski and Jenna Fischer as Jim and Pam on The Office

(Image credit: NBC)

5. “Diversity Day” (Season 1, Episode 2)

The Office came out swinging with their second-ever episode, “Diversity Day.” To combat Michael’s constant quoting of a certain Chris Rock comedy routine, corporate decides to send a representative to engage the Scranton branch in a diversity seminar. 

Michael is pretty sure he could do a better job of putting on Diversity Day, so he organizes an activity in which everyone will tape an index card to their forehead with the name of a race or ethnicity. The employees then have to interact with each other based on how they’d treat a person of that race. Michael’s card of course says “Martin Luther King Jr.”

The chaos culminates in Michael’s super racist impression of an Indian person, and Kelly (played by one of The Office's writers, Mindy Kaling) slaps him across the face. It’s deserved, and it makes for one of the worst Michael moments of the entire series.

Michael (Steve Carell) and Oscar (Oscar Nunez) share an uncomfortable kiss

(Image credit: NBC)

4. “Gay Witch Hunt” (Season 3, Episode 1)

After accidentally outing Oscar (Oscar Nuñez) to the entire office, Michael tries to make amends by holding a homosexuality seminar.

Oscar finds the whole thing pretty offensive, and threatens to quit—so in an attempt to demonstrate his tolerance for gay people, Michael forces him into a kiss in front of the entire office.

The moment actually wasn’t even scripted—Steve Carell made the decision to kiss Oscar Nuñez in the middle of shooting the scene. Nuñez revealed the secret in “Gay Witch Hunt w/ Oscar Nuñez”, an episode of the Office Ladies podcast hosted by Jenna Fischer and Angela Kinsey.

It’s not all bad for Oscar, though. After suffering through one of the most awkward Office encounters of all time, he gets three months paid vacation and a company car to make up for Michael’s behavior.

A pizza delivery boy (Kevin McHale) held hostage in the conference room

(Image credit: NBC)

3. “Launch Party” (Season 4, Episodes 5 & 6)

This episode is disastrous from start to finish. It begins with news of a launch party for Dunder Mifflin’s new website, Dunder Mifflin Infinity. Michael receives an invitation to the party and happily makes his way to New York, only to find out that the invitation was really a link to a virtual party.

Michael tries to make the Scranton branch party better than the party he wasn’t invited to by ordering a boatload of pizzas, which he plans to pay for with a half-off coupon. The teenage delivery driver can’t accept the coupon, so Michael and Dwight do what any reasonable adult would do in that situation: kidnap him and hold him hostage.

This unbearable episode would crack the top 3 based on the kidnapping alone, but it also includes Andy’s conference call performance of “Take A Chance on Me” by ABBA.

Jan (Melora Hardin) shows off a CD made by her former assistant, Hunter

(Image credit: NBC)

2. “Dinner Party” (Season 4, Episode 13)

After coercing his coworkers into attending a dinner party at his condo, Michael and his girlfriend Jan (Melora Hardin) host the most uncomfortable social event of all time.

During the course of the evening, we learn that Michael sleeps on a small bench at the foot of Jan’s bed, his prized possession is a tiny plasma TV, and Michael has gotten three vasectomies to appease Jan.

The night continues to devolve into wackiness, with Jan attempting to convince everyone to invest in her candle-making business and ultimately sharing a suggestive song written by her former assistant, Hunter, seen at the beginning of this clip:

The night ends with a broken TV, a broken Dundie, and cops at the front door. It’s incredibly uncomfortable to watch, but probably not as uncomfortable as sleeping on Michael’s bench. It's hard to imagine an episode that could cause more second-hand embarrassment than "Dinner Party."

Michael Scott (Steve Carell) cries while visiting students in the episode "Scott's Tots"

(Image credit: NBC)

1. “Scott’s Tots” (Season 6, Episode 12)

No surprise here: The number one episode on our list is “Scott’s Tots,” the episode where Michael must come face to face with a promise he made 10 years prior to pay for the college educations of a local 3rd grade class of underprivileged children. Michael shares his thoughts on Scott’s Tots before visiting the school:

I’ve made some empty promises in my life, but hands down that was the most generous.

Michael made the promise on the assumption that he would one day be extremely wealthy, but that hasn’t panned out—so he has to tell the now-high school seniors, who greet him with song, dance, and applause, that he actually won’t be paying their tuition after all.

The biggest cringe from “Scott’s Tots” is the performance the students put on for Michael before he comes clean, complete with the rousing lyrics, “Hey Mr. Scott, whatcha gonna do, whatcha gonna do, make our dreams come true.”

Michael tries to cover up his mistake by gifting all the students with laptop batteries instead. It’s an episode you won’t be able to watch without occasionally face-palming.

A Ben Franklin impersonator flirts with Pam (Jenna Fischer)

(Image credit: NBC)

Honorable Mention For These Super Cringey Moments

Plenty of episodes of The Office aren’t quite as cringe-worthy as the ones on our list, but that doesn’t mean they aren’t full of uncomfortable scenes. Here are some honorable mentions for moments that will make you wince with second-hand embarrassment.

  • Michael proposes to Carol after 9 dates (Season 3, “Diwali”)
  • The Ben Franklin impersonator hits on Pam (Season 3, “Ben Franklin”)
  • Michael cleaning pumpkin off his windshield after firing Devon (Season 2, “Halloween”)
  • Michael and Dwight’s karate battle (Season 2, “The Fight”)
  • Stanley disrespects Michael, who responds later by pretending to fire him. (Season 4, “Did I Stutter?”)
  • Michael burns his foot on a George Foreman grill (Season 2, “The Injury”)
  • Angela grooming her cats (Season 5, “Lecture Circuit: Part 2)
  • Dwight destroys Jan’s expensive stroller (Season 5, “Baby Shower”)

Episodes of The Office are available to stream with a Peacock subscription.

Emily Marek

She/her. Lover of female-led comedies, Saturday Night Live, and THAT scene in Fleabag. Will probably get up halfway through the movie to add more butter to the popcorn.