The 25 Best Moments From ‘The Office’

The term “cringe humor” was first introduced to many people as The Office was taking off, and there are countless cringey moments on the show that still sting after several re-watches. But none of them compare to this infamous Season Six episode, written by the brilliant duo of Gene Stupnitsky and Lee Eisenberg. (Their episodes often presented Michael in the most pathetic fashion possible.) It revolves around a promise Michael made years ago to pay for the college tuition of an entire class of underprivileged third graders. They’re about to graduate, and Michael needs to tell them he can’t honor the deal. The big reveal comes after they perform an elaborate song and dance routine for him, praising his extreme generosity. It’s hilarious in the most agonizing of ways.Best Line: “Hey, Mr. Scott, whatcha gonna do? Whatcha gonna do to make our dreams come true?”

It feels absolutely ludicrous that Michael Scott was placed in charge of the Dunder Mifflin branch in Scranton until you realize that he has one very important skill: He’s an excellent salesman. “To me, it’s all a comment on what I’ve seen at real places,” said writer Paul Lieberstein, who also played Toby. “They will make every excuse in the book for someone who’s bringing in a lot of money.” This idea first becomes clear in the “The Client,” when Michael seems to be blowing a very important meeting with a representative for Lackawanna County, played by Tim Meadows, until he puts in the hard sell after establishing a bond with him. A flummoxed Jan is stunned, and she drives off with him at the end.It was the beginning of their doomed relationship. Best Line: “Here’s the thing about those discount suppliers. They don’t care. They come in, they undercut everything, and they run us out of business, and then, once we’re all gone, they jack up the prices.”

Years ago, Office writer Jen Celotta’s parents had a Honda Odyssey Minivan. She looked through the GPS manual one day and read, “No matter what your GPS tells you to do, do not drive into a body of water.” She thought to herself, “Who the fuck would drive into a body of water?” The idea hit her all at once: “Michael Scott would drive into a body of water!” It inspired a great scene where Michael misunderstands GPS directions and drives right into Lake Scranton with Dwight in the passenger seat. (Any Scranton native will tell you that driving a car into Lake Scranton isn’t technically possible.)Best Line: “This is the lake! This is the lake! No, there’s no road here!”

There are many aspects of Dwight Schrute that don’t quite go together. He’s a quasi-Amish beet farmer, a science fiction and fantasy buff, a heavy metal fan, and an irresistible ladies man. (Rainn Wilson somehow makes all of these aspects of the character believable, no matter how incongruous.) Most importantly for the show, he is also a gifted salesman. In the Season Two episode “Dwight’s Speech,” he’s given the Northeastern Pennsylvania Salesman of the Year award. He doesn’t know what to say until Jim gives him the text of a speech by Benito Mussolini, which he unwittingly delivers to thunderous applause.Best Line: “Blood alone moves the wheels of history!”

This could easily be a list of the 25 best pranks that Jim plays on Dwight, but we’re going to limit ourselves to only a handful of the very best ones. That has to include Asian Jim, especially since moments from the painfully inert Michael Scott-free Seasons Eight and Nine are going to be very scarce on this list. It’s a relatively simple one where guest actor Randall Park shows up to work in Jim’s place, and freaks the hell out of Dwight by pretending to be him. There’s even a framed, Photoshopped image of Park with Pam and their supposed kids on Jim’s desk. This is after nearly a decade of absurd pranks, and Dwight somehow still buys it. (Just last year, Park revived his Asian Jim bit alongside Ryan Reynolds in a promotional video for John Krasinksi’s movie If.)Best Line: “You seriously never noticed? Hats off to you for not seeing race.”

We first learn that Michael Scott has written the screenplay for a spy movie called Threat Level Midnight in the Season Two episode “The Client.” But we don’t find out he actually spent years shooting it with the Dunder Mifflin crew until this episode, written by B.J. Novak. Predictably, the story is a crazy amalgamation of all sorts of bad movies, complete with a scene where Agent Michael Scarn does his signature dance routine the Scarn at a bar with a bunch of locals, including, for some reason, an Opie-like boy in overalls. “A big problem was people laughing,” said Office producer Steve Burgess, “when they weren’t supposed to be because it was just so funny.” Years later, “the Scarn” got a second life when Office superfan Billie Eilish sampled some of the dialogue in her song “My Strange Addiction.”Best Line: “Well, my name’s Michael Scarn and I’m here to say/I’m about to do the Scarn in a major way.”

According to the scientific principle of impenetrability, two objects of matter cannot occupy the same space at the same time. That’s why the U.K. Office team never visited the Scranton branch of Dunder Mifflin. It would have made no sense for Tim and Dawn to meet Jim and Pam and realize they’d lived almost identical lives on opposite sides of the Atlantic. But near the end of Steve Carell’s tenure on the show, the writers simply couldn’t resist cooking up a brief moment by an elevator bank where Michael Scott finally encounters Ricky Gervais’ David Brent. In the course of a single minute, they break out dueling racist Asian characters, and explain why people shouldn’t be offended by such things. “People don’t understand,” says Scott. “It has nothing to do with making fun of a different nationality.” It was smart to keep this blessed moment brief, but we’re all grateful it happened. And somehow, it didn’t create a rift in the space-time continuum and wipe out all life on the planet.Best Line: “Comedy is a place where the mind goes to tickle itself…That’s what she said.”

In one of the key climactic scenes of the U.K. Office, Tim confesses his feelings for Dawn in a conference room without their mics on. The audience never hears what he actually says, but we see a serious conversation through blinds that ends with them hugging. He goes back to his desk, picks up his mic, and says “She said no, by the way.” This was nearly repeated on the U.S. Office, when Jim proposes to Pam in the Season Five episode “Weight Loss,” but showrunner Greg Daniels decided at the last minute that audiences deserved to hear the moment. At the end of the season, however, they did kill the audio when Jim and Pam learn they’re having a baby in “Company Picnic.” We can tell what happened by the joyful looks on their faces, and the actual dialogue is left to our imaginations.Best Line: “Hey, Dwight. Uh… send in the subs.”

As all true Office fans know, Creed Bratton isn’t just the weird old man in the corner who smells like mung beans. He also played guitar in the Sixties folk-rock band the Grass Roots, both in real life and in the reality of the show. (The scene where he revealed this in “Booze Cruise” was cut but still canonical.) Bratton’s musical gifts were mostly hidden on The Office, but in the last episode he was allowed to sing his original song “All the Faces” in the show’s closing minutes. It’s very hard to hear it today and not feel the emotion of that moment.Best Line: “I saw a friend today, it had been a while/And we forgot each other’s names/But it didn’t matter because deep inside/The feeling still remained the same.”

After years of disastrous relationships, the perfect woman for Michael finally entered his life when temporary human resources director Holly Flax (Amy Ryan) came to Scranton to sub in for Toby. She shared Michael’s juvenile sense of humor, boundless love for conference room meetings, and even had her own bad impersonations of Yoda and the Terminator. It took two seasons for them to come together at the right moment, culminating in a candlelight proposal in front of the entire office that sets off the sprinkler system. Even in this moment, Michael can’t resist breaking out his Kermit the Frog impression.Best Line: “Holly Flax, marrying me, will you be?”

The Office was nearly cancelled after the first season because audience members had a hard time connecting to Michael Scott. In those early days, he was an unlikeable jerk who laughed at Pam’s tears after he pretended to fire her. So, at the start of the second season, the writers were tasked with giving Michael heart. They had to show that his outlandish behavior was an outgrowth of a desperate need for friends and acceptance — and they pulled it off in the premiere episode, when a group of fratty dudes at a bar pummel Michael with rags as he’s hosting an awards show for the office. He’s humiliated and wants to stop the ceremony, but a drunken Pam rallies everyone behind him. He beams with joys as he hands out awards like Bushiest Beaver to Phyllis. (It was supposed to read Busiest Beaver.) This was a major turning point for the character, and the kickoff of the show’s greatest season. Best Line: “I feel God in this Chili’s tonight.”

A quick Google search shows at least 100 different unofficial Office T-shirts for sale printed with just four words: “Bears Beets Battlestar Galactica.” As nearly all Office die-hards know, that refers to a classic Season Three Jim prank where he comes to work dressed up exactly like Dwight, down to his calculator watch and mustard yellow tie. Within a period of about 15 seconds, Dwight’s reaction goes from indifference to confusion to calmness and finally rage. “Identity theft is not a joke, Jim,” he says. “Millions of families suffer every year.”Best Line: “Michael!”

Scratchy finally got revenge against Itchy on one episode of The Simpsons after years of torture. And in Season Seven of The Office, Dwight finally got revenge against Jim after years of elaborate pranks. It starts when Jim throws a single snowball at Dwight in the office, and refuses to apologize. Dwight retaliates by pummeling Jim bloody with a bag of snowballs, and eventually scares the living shit out of him in the parking lot by setting up a bunch of spooky snowmen in a scene straight out of an Alfred Hitchcock movie. Good for Dwight. He finally got to win something.Best Line: “I have no feeling in my fingers or penis, but I think it was worth it.”

After Kelly tampers with the results of a customer survey and convinces Michael that Jim and Dwight’s clients are unhappy, Dwight is forced to hold a mock sales call with Jim to improve his performance. Dwight and Michael take it very seriously. Jim does not. And after introducing himself as Bill Buttlicker, he puts Dwight on hold to take another mock call. “I’m just on the phone with this stupid salesman,” Jim says. “He’s so dumb. Probably going to keep him on the line forever and not buy anything.” What sells the scene is Steve Carell’s stone-faced commitment to the bit, and his genuine joy when William M. Buttlicker buys a million dollars of paper products. Best Line: “Buttlicker! Our prices have never been lower!”

In the second season of The Office, Jim is madly in love with Pam and can’t do a thing about it since she has a fiancé. The formula is flipped in the third season, when a now-single Pam pines after Jim, who returns to Scranton with a girlfriend. In the penultimate episode of the season, Michael forces the team to compete in a series of beach games for a promotion. Near the end, Pam gathers up the courage to walk across hot coals — and vents her frustrations with Jim in front of the entire office. “Jim, I called off my wedding because of you,” she says. “And now we’re not even friends. And things are just, like, weird between us, and that sucks. And I miss you.” It was a moment of honesty that set the stage for them to finally get together.Best Line: “There were a lot of reasons to call off my wedding. But the truth is, I didn’t care about any of those reasons until I met you.” @peyton_mackenzie love pam here #theoffice #pambeesly #jimhalpert ♬ original sound – Peyton ⭐️🎶🎬

The truncated first season of The Office is a pretty mixed bag, because it had yet to fully separate itself from the U.K. show. The Michael Scott character was still highly unsympathetic, and he had a slicked-back haircut that was oddly distracting. But they managed to make one timeless episode with “Diversity Day,” where the gang goes through diversity training and eventually winds up wearing signs on their foreheads that read things like Jewish, Jamaican, Italian, and Black. This goes about as disastrously as it sounds, and it culminates with Michael speaking to Kelly in an absurdly stereotypical Indian accent before she slaps him in disgust.Best Line: “You’ll notice I didn’t have anybody being Arab. I thought that would be too explosive. No pun intended. But I just thought, ‘Too soon for Arabs.’ Maybe next year. Um… You know, the ball’s in their court.”

All that Michael wanted in life was a loving wife, kids, a house with a white picket fence, and the occasional backyard ketchup fight. He eventually gets there by the end of the series, but it was a long journey filled with many wrong turns. He hit a low point during his long, horrid relationship with his onetime boss, Jan Levinson (Melora Hardin). She moves into his condo after losing her job, and we finally see their home life together in “The Dinner Party.” Early in the episode, Michael takes Jim and Pam around the house and reveals way more about the misery of his life than he intends. We see Jan’s office, her candle studio, Michael’s tiny plasma television, and the tiny bench where Michael sleeps at the foot of their king size bed. (This isn’t a ranking of the best Office episodes, though if we ever do that, spoiler alert… “The Dinner Party” is going to win. Click here for an extremely deep dive into the episode.)Best Line: “Sometimes, I will just stand here and watch television for hours.”

When the third season of The Office came around, actor Oscar Nuñez, who played Oscar Martínez, needed a bit of time off to work on another project. To pull this off, the writers came up with an episode where Michael learns Oscar is gay, kisses him on the lips in front of the entire office, and Oscar winds up with a three-month leave of absence in exchange for an agreement to not sue the company. Amazingly, the kiss wasn’t in the original script. Carell simply went for it after four boring takes where they merely hugged. “Thank God Oscar is a genius and he had improv training,” said writer Jen Celotta. “He did not break, but we had to work to find a reaction where everyone wasn’t breaking since this wasn’t supposed to happen.” Best Line: “I did it. See, I’m still here. We’re all still here.”

Michael Scott moved out of Scranton near the end of Season Seven to live with Holly in Boulder, Colorado, and was rarely referenced again. As the series started to wind down in Season Nine, speculation was rampant that Michael would return for the grand finale. The cast and crew denied this was going to happen over and over, but Carell did come back for two quick scenes at Dwight’s marriage to Angela. Michael landed a “that’s what she said” joke, of course, but the focus remained on the other characters. “I didn’t want it to be a big thing,” said Carell. “I did it out of respect for the show and the actors.” It also gave the fans a final glimpse of Michael, finally living the life he always wanted to live.Best Line: “I feel like all my kids grew up, and then they married each other. It’s every parent’s dream.”

Midway through its fifth season, NBC gave The Office a chance to run an episode immediately following the Super Bowl. This was an opportunity to expose the show to a massive audience, and the creative team wanted to start with a huge moment to stop people from turning off their TVs. After much debate, they went with Dwight throwing the office into absolute chaos by staging a mock fire. Kevin raids the candy machine, Oscar climbs up into the ceiling, Stanley suffers a heart attack, and Angela reveals that her cat Bandit has secretly been living in a drawer. She throws him up to Oscar, but he falls right back down and ricochets hard off a desk. The Bandit moment lasts only about three seconds, but required two stunt cats, an animal trainer, and the creation of a $12,000 stuffed replica of Bandit they didn’t even wind up using. It was worth all the hard work. Nearly 23 million people watched the episode, and it won an Emmy for Outstanding Directing for a Comedy Series.Best Line: “I only weigh 82 pounds!”

For reasons that are hard to understand, Steve Carell never won an Emmy for his portrayal of Michael Scott. In a just world, he’d have a shelf full of them. One early moment that sums up his award-worthiness is the monologue he delivers in “The Injury,” where he explains how he accidentally barbecued his foot on a George Foreman grill. It’s an act so preposterously stupid — involving waking up in the morning, setting bacon strips on a Foreman near his bed, and returning to sleep so he could wake up to the smell of cooked bacon — that few actors would be able to sell it as something that really happened. Yet Carell pulled it off with ease. (Mindy Kaling deserves a lot of credit for writing the monologue.)Best Line: “I like waking up to the smell of bacon, sue me. And since I don’t have a butler, I have to do it myself.”

Steve Carell’s final episode was a highly emotional shoot for the cast and crew of The Office. This transferred well onto the screen, since the actors were saying goodbye to their colleague as much as Dunder Mifflin employees were saying goodbye to their boss. Michael has a little moment with nearly all of them, but Pam skips work to attend a screening of The King’s Speech, thinking Michael still has one more day. When she learns the truth, she runs to the airport, somehow gets past security, gives him a hug, and whispers something into his ear the audience can’t hear. When we first saw them together in the pilot, Pam had little patience for Michael’s antics, and was furious when he pretended to fire her. But their relationship grew and matured over the years, and she was genuinely crushed to see him go. “I told him all the ways I was going to miss him when he left our show,” Jenna Fischer said years later. “Those were real tears and a real goodbye.”Best Line: “Hey, will you guys let me know if this ever airs?”

Michael Scott had many great alter-egos, including Michael Klump, Blind Guy McSqueezy, Date Mike, Mykonos, and Michael Scarn. (It’s best to pretend Ping wasn’t a thing.) But his most hilarious character was Prison Mike, who came out midway through the third season after Scranton’s Dunder Mifflin team learned one of their new colleagues had briefly served time. Like most of Michael’s characters, Prison Mike was based on loose caricatures Michael had seen in bad movies and TV shows over the years. “The worst thing about prison was the Dementors,” Prison Mike tells the crew, confusing prison with the magical world of Harry Potter. “They were flying all over the place, and they were scary, and they came down and sucked the soul out of your body.”Best Line: “Do you really expect me not to push you up against the wall, biatch?”

There’s a lot happening in the first two seasons of The Office, but the central storyline is Jim’s desperate crush on Pam. She clearly has feelings for him, too, but can’t act on them because she’s engaged to Roy, a warehouse worker who’s painfully wrong for her. At the end of the Season Two finale, Jim gathers up the nerve to tell Pam how he feels when they’re alone in the parking lot following a night of casino games in the warehouse. “I was just… I’m in love with you,” he says. “I’m really sorry if that’s weird for you to hear, but I needed you to hear it. Probably not good timing, I know that…I just needed you to know, once.” She doesn’t know how to respond or even feel, but tells him she’s sorry if he “misinterpreted things.” He walks away with tears in his eyes, but reemerges in the office when she’s calling her mother and kisses her, wrapping up one of the greatest seasons in television history.Best Line: “I don’t know, Mom. He’s my best friend.”

It was extremely hard (that’s what she said) to pick the singular greatest moment in the history of The Office. We weighed various Jim and Pam moments, key scenes where Michael Scott showed real growth, or even the best Jim and Dwight pranks. But in the end, we went with Kevin spilling chili all over the floor. The cold open lasts a mere 36 seconds, has nothing to do with the episode, and Kevin Malone (Brian Baumgartner) is the only character we see. But the contrast between the audio of him explaining how he cooks his delicious chili and footage of him spilling it on the floor and caking it all over himself as he pathetically tries to scoop it back in never stops being funny. It would have been funny in a silent movie from 1902. It’ll be funny 500 years from now. And Brian Baumgartner executes the scene flawlessly. It’s such a beloved moment that he wrote his own chili cookbook a few years back. (Office trivia: Aaron Shure wrote the scene, which was originally a bit longer and included a moment where Jim and Andy show up and wonder why the office smells like chili. Read the original draft here.)Best Line: “The trick is to undercook the onions. Everybody is going to get to know each other in the pot.”