For many, The Office is background music. The beloved series still plays on a loop across streaming services and cable providers in homes around the world. It’s the ensemble cast, their relatable stories, and familiar setting that make it all so comforting. Rarely, if ever, has there been a program that reached into the hearts of viewers and made them relate to so many different characters at once. The diverse cast may have been its most popular attribute, but not for the reasons many might think. It was often these attributes and the misplaced attempts by Michael Scott to “accept” them that made them so vital to the story. In many ways, the tales from Scranton centered less around the financial growth of Dunder Mifflin and more about the personal growth of Scott himself.
Steve Carell’s main character wasn’t bigoted like Archie Bunker in the All in the Family sense, just misguided. His wide-eyed approach to anyone different from him resulted in some hilarious memories. These memories, however, might be a bit outdated by today’s standards. As Mindy Kaling, The Office’s Kelly Kapoor and writer on the program, told Good Morning America, much of The Office wouldn’t fly today. Many people couldn’t believe it, but a look at our favorite moments prove that, well, she kind of has a point.
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6 Goodbye Toby — Season 4, Episode 14
NBC
This episode celebrated Michael Scott’s biggest triumph: the (unknowingly temporary) departure of his nemesis in human resources. It was also where he found Holly, his eventual wife. It was a beautiful love story with the typical teeth-clenching Michael moments behind it. It’s also one of the few where the boss isn’t the centerpiece of cringing controversy.
MOVIEWEB VIDEO OF THE DAY
MOVIEWEB VIDEO OF THE DAY
MOVIEWEB VIDEO OF THE DAY
In this episode, it’s Dwight Schrute. In an act of hazing, he tells Holly that the perpetually sloth-like Kevin Malone is “special.” His hiring, Dwight explains, is an act of charity. It causes Holly to baby the child-like accountant and show him extra attention. Kevin’s response to the camera, “I am totally going to bang Holly.”
The episode, similar to Arrested Development’s season three storyline, was one that was hilarious at the time. In hindsight, it is even fun to watch. It is, however, difficult to imagine a program today getting away with it. In cases like this, it’s the cherished memory of these characters that makes moments epic where another cast would be scrutinized.
5 Women’s Appreciation — Season 3, Episode 21
NBC Universal
When Phyllis is flashed in the parking lot, Michael asks, “Why Phyllis? Did he even see Pam? Or Karen from behind?” He also puts his finger through the fly of his pants and runs around wagging his tongue. This may be the reason why Michael Scott spent seven seasons searching for love. The fact that he ever found it shows that there’s hope for anyone.
Then again, he did take the women of Dunder Mifflin out for a shopping trip at the mall in celebration of Women’s Appreciation Day. That’s nice. He even treated them all to lingerie at Victoria’s Secret. That part’s a little weird.
4 Gay Witch Hunt — Season 3, Episode 1
The most unbelievable part about this episode? It isn’t Michael and Dwight going around “hunting” the gay office employee that makes it so offensive. It was Michael forcing Oscar, the gay employee, to kiss him on the mouth in front of the entire staff despite his muttering pleas of “No, please don’t” that makes it so offensive. Granted, Oscar was given a settlement by the company for this insanity, but still, yikes.
In one of the most amazing demonstrations of Michael’s poor decision-making, we watch as the boss decides that a forced kiss will prove his love of a gay man in the workplace. It’s almost too wild to comprehend, but once you understand Michael, you can almost see his warped reasoning. Live at the Paleyfest in 2007 (via The Futon Critic), Carell said of this episode, “It spoke to the fact that Michael is not a homophobe; he just doesn’t understand the world.”
3 A Benihana Christmas — Season 3, Episode 10
One of the first episodes to receive upturned eyebrows long after it aired was “A Benihana Christmas.” This festive special featured Michael heading to the traditional Japanese restaurant for a night of fun. It ends with him and Andy taking two of the waitresses to the Christmas party back at the office. Realizing he can’t tell the two women apart, Michael marks one with a sharpie. It’s a bit, um, “out of touch” on a number of levels. On The Office Ladies podcast with Jenna Fischer and Angela Kinsley, the two admitted that they cringed when rewatching the episode.
Years later, Kat Ahn, one of the two waitresses, expressed unhappiness with her appearance. In a TikTok video and in speaking with USA Today, she stated, “The storyline with myself and the other Asian American actress is that we were the uglier versions of the actresses at the Benihana. Also that all Asian people look alike. We’re one big monolith and just one big walking stereotype without any personality or any individuality, which is problematic. The whole joke was that all Asians look alike and that’s why Michael Scott couldn’t tell us apart.”
2 Product Recall — Season 3, Episode 21
What is it about this one? Could it be the obscene watermark accidentally printed on reams of paper showing a duck and a mouse being intimate? Nope. Could it be Creed, responsible for quality assurance, getting a random woman fired for his own mistake? Nope. Instead, it was Andy Bernard finding out that he was dating a girl in high school. That’s it.
The shocking reveal happened when the 30-something salesman found himself on location to speak with school administrators about the paper error. While walking the hallways with Jim “Big Tuna” Halpert, he spotted his love interest at her locker. It results in a very uncomfortable exchange that sees Nard Dog neutered. There aren’t too many shows today about adult men discovering that they accidentally dated an underage girl. Then again, there aren’t a lot of shows like The Office.
1 Diversity Day — Season 1, Episode 2
Perhaps the best example of Michael’s clueless nature was Diversity Day. This dumpster-fire idea was carried out Michael’s resentful response to a corporately-mandated diversity seminar. The reason they held the seminar: his retelling of a Chris Rock standup act rife with racial slurs. Still, that’s not the reason this episode is at the top of the list.
To counteract this seminar, which Michael insists he learned “nothing” from, he holds a meeting of his own. Each member of the staff wears an ethnicity on their head and needs to guess who they are by how they are treated. Needless to say, this one hits everyone. Whatever color, religion, or nationality you can think of, they tried to work it in.
Written by B.J. “Ryan Howard” Novak, this episode has one of the most shocking and poignant moments in the show’s history. In a frenzied state and unhappy about the lack of participation, Michael tries to demonstrate the game to Kelly, who is walking into the meeting late from a phone call. He approaches the Indian actress and puts on an exaggerated Indian accent. He then says to her, verbatim: “Kelly! How are you! Oh, welcome to my convenience store. Would you like some cookie cookie? I have some very delicious cookie cookie. Only 99 cents plus tax! Try my cookie-cookie! Try my cookie-cookie! Try my cookie-cookie! Try my…” And she slaps him.
Kelly’s face as she watches this confusingly racist display, the sting of her slap, and Michael’s attempt to fight back tears afterward speaks volumes for all the actors involved. The moment demonstrated all of Michael’s naivety about true diversity and his obliviousness to appropriate behavior. Some might not understand why he’s so beloved by the generations that came up watching him. When it comes to Michael Scott, you just had to be there.
