It’s time to head back to The Office. On March 24, 2005, NBC aired the pilot episode of the iconic workplace mockumentary chronicling the inner workings of the Dunder Mifflin Paper Company’s branch in Scranton, Pennsylvania, as its employees faced downsizing by corporate. “What is the most important thing for a company? Is it the cash flow? Is it the inventory?” asked Regional Manager Michael Scott (Steve Carell), the obnoxious but self-declared “World’s Best Boss.” “Nuh-uh. It’s the people.”
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The people person’s paper people like salesman and Assistant to the Regional Manager Dwight Schrute (Rainn Wilson), camera-mugging prankster Jim Halpert (John Krasinski), long-suffering receptionist Pam Beesly (Jenna Fischer), and new temp Ryan Howard (B.J. Novak).
Nine seasons and 201 hilariously awkward or downright cringeworthy episodes later, The Office continues to leave fans satisfied and smiling. We’ve thought about it long and hard (that’s what she said), and these are the 20 best episodes of The Office most deserving of a Dundie:
20. Scott’s Tots (Season 6, Episode 12)
The infamously cringe-inducing “Scott’s Tots” episode of The Office is emblematic of how the well-meaning Michael Scott desperately wants to be liked, to the point of pledging to pay the college tuition of an entire class of third graders dubbed “Scott’s Tots.” A cackling Stanley (Leslie David Baker) gleefully reminds Michael that 10 years have passed, and it’s time to settle up.
Michael — who sincerely believed he’d be a millionaire by the time he was 30, and then 40, but by then “had less money than when I was 30” — is forced to visit the school with Erin (Ellie Kemper) and admit the truth. After sitting through a session where Scott’s Tots literally sing his praises (“Hey, Mr. Scott! What you gonna do? What you gonna do, make our dreams come true!”), Michael confesses he won’t be paying for their tuition. Although he offers to compensate Scott’s Tots with lithium laptop batteries in lieu of tuition, Michael is left with the knowledge that he “destroyed 15 young lives.” Ooof.
“I’ve made some empty promises in my life, but hands down, that was the most generous.”
— Michael Scott
19. Murder (Season 6, Episode 10)
When it’s discovered that Dunder Mifflin is about to declare bankruptcy, sending the office into a panic, co-managers Michael and Jim clash over Michael’s decision to declare (with a Southern twang) that “there’s been a mur-dah in Savannah.” As a distraction, Michael prompts a game of Belles, Bourbon, and Bullets: A Murder Mystery Dinner Party Game, a whodunnit with a molasses-mouthed Andy (Ed Helms) trying to decipher if he asked out Erin or her roleplay character, “Naughty Nellie.”
The best moment of the episode comes when accountant Oscar (Oscar Nunez), who has been keeping tabs on Dunder Mifflin rather than playing the game, is forced to relay an announcement about the company’s liquidity in-character with a high-pitched southern accent: “This plantation, we’re running low on greenbacks. We’re having problems paying the people who give us the seeds and the dirt. We can’t pay!”
Plus, Creed (Creed Bratton) shows up late and promptly flees when Michael, speaking as playboy Caleb Crawdad, tells him that “there has been a murder, and you are a suspect.”
“Now do the Swedish Chef.”
“Uh, not familiar. What province is he from?”
“He lives on Sesame Street, dumbass.”
— Kevin and Andy
18. Money (Season 4, Episodes 7-8)
After three seasons of Will They/Won’t They, “Money” sends new couple Jim and Pam to Dwight’s Schrute Farms for an overnight stay (which Dwight insists is “agrotourism,” not a bed and breakfast). Meanwhile, Michael quite literally declares bankruptcy before running away, rather than tell lover Jan (Melora Hardin) about his financial struggles (due in part to Jan’s spending and mounting credit card debt from frivolous purchases like The Muppet Show DVDs and the Core Blaster Extreme).
The (ahem) core of the episode, however, is a tender moment in the typically antagonistic relationship between Jim and Dwight. With Andy successfully wooing Dwight’s ex Angela (Angela Kinsey), Jim commiserates with Dwight when he recalls leaving Scranton because of Pam’s relationship with her former fiancé Roy (David Denman). “It was awful. It was something that I wouldn’t wish on my worst enemy,” Jim says, “and that includes you.”
“I… DECLARE… BANKRUPTCY!”
“Hey, I just wanted you to know you can’t just say the word ‘bankruptcy’ and expect anything to happen.”
“I didn’t say it, I declared it.”
— Michael and Oscar
17. Diversity Day (Season 1, Episode 2)
After Michael recites a Chris Rock routine, corporate brings in diversity sensitivity trainer Mr. Brown (Larry Wilmore) for a seminar that quickly becomes uncomfortable. Michael is bleeped while doing his Chris Rock impression, and in another instance of secondhand embarrassment, insists the office is “very advanced in terms of racial awareness” as he refuses to sign a form pledging he learned something about offending his coworkers in the workplace.
Michael mounts his own program, “Diversity Tomorrow (because today is almost over),” and misappropriates an Abraham Lincoln quote before prompting an offensive exercise: a race guessing game. Michael being Michael, he takes it too far when he’s slapped by Kelly (Mindy Kaling) for his impression of an Indian person. (“Now she knows what it’s like to be a minority,” Michael, on the verge of tears, says of Kelly, who is Indian.)
“This is an environment of welcoming and you should just get the hell out of here.”
— Michael to Toby
16. Email Surveillance (Season 2, Episode 9)
By taking the employees out of the office, “Email Surveillance” gets into the interpersonal relationships: Jim’s crush on the engaged Pam; Pam’s suspicions that Dwight and Angela are dating; and Michael’s hurt feelings over not being invited to a BBQ at Jim’s apartment. After Michael is left behind by his improv class (who are fed up with his finger-gunned FBI Detective Michael Scarn), he uncomfortably crashes the party despite not being invited.
As obnoxious and offensive as he can be, it’s heartbreaking watching a rejected Michael — who considers his coworkers to be family — be left out because he’s obnoxious and offensive. And that’s why it’s heartwarming when Jim joins Michael in a karaoke duet of “Islands in the Stream.”
“I think one of the greatest things about modern America is the computerization of medical records. As a volunteer sheriff, I can look up anyone’s psychiatric records or surgical histories. Yeast infections. There are a huge number of yeast infections in this county. Probably because we are down river from that old bread factory.”
— Dwight
15. Niagara (Season 6, Episodes 4-5)
One called-off engagement, two weddings, and six seasons later, The Office‘s fan-favorite couple became officially official as Jim and Pam married at Niagara Falls. Of course, this being a two-part wedding episode, there’s Michael-isms (“I’ll see you in Viagara Falls”), mishaps (Andy’s scrotum-puncturing splits), and mental pictures (Jim and Pam’s way of mentally documenting the high points).
After sneaking away to get married aboard the Maid of the Mist before their church ceremony, Jim and Pam — with a cut tie and torn veil — snap mental shots as their friends and family dance down the aisle in a sequence recreating the viral YouTube video “JK Wedding Entrance Dance.”
“I bought those tickets the day I saw that YouTube video. I knew we’d need a backup plan. The boat was actually Plan C, the church was Plan B, and Plan A was marrying her a long, long time ago. Pretty much the day I met her.”
— Jim
14. Goodbye, Toby (Season 4, Episodes 18-19)
Michael sends off his archnemesis — “His Horribleness,” Human Resources rep Toby Flenderson (Paul Lieberstein) — with a going away party. Tasking Phyllis (Phyllis Smith) with heading the party-planning committee (and the impossible task of finding an anti-gravity machine), Michael then takes it upon himself to haze Toby’s replacement: Holly Flax (Amy Ryan).
When Michael finds himself falling for the “female Toby” despite his prejudice against HR — “My job is to make the office fun, your job is to make the office lame,” he explains — it’s too late to rein in Dwight, who convinces Holly that dim-witted accountant Kevin (Brian Baumgartner) is “slow.” Meanwhile, Andy accidentally thwarts Jim’s proposal plans when he usurps Toby’s going away party to propose to Angela (who Phyllis catches having an affair with Dwight), Michael finds out his ex, Jan, is pregnant, and in another shakeup to the status quo, Ryan (then VP of Northeastern Sales) is arrested for fraud to end season 4.
“Toby is going away forever, and we need to do something very, very special. In some cultures, when somebody leaves, like New Orleans culture, they have a parade and they have a band and people party in the streets.”
“Do you mean ‘leaves’ as in dies? You want us to throw Toby a New Orleans funeral?”
“If the Devil were to explode, and evil were gone forever, what sort of party would you have?”
— Michael and Pam
13. The Negotiation (Season 3, Episode 19)
While Jim tries to repay Dwight for defending him from an enraged Roy (who found out in the previous episode that Jim kissed Pam), Michael uses the list of negotiation tactics he downloaded on Wikipedia when warehouse foreman Darryl (Craig Robinson) comes to him to negotiate a raise.
Darryl convinces Michael to ask for his first raise in 14 years, so they head to Dunder Mifflin Corporate, where Michael recounts the events of the day to Jan: “I accidentally cross-dressed, and then Darryl made me feel bad for not making any money, and then I had to ride up here with stupid Toby, and then your assistant was all young and hot.”
“I remember it was very late at night, like 11, 11:30. Big fella comes in screamin’ about God knows what. I think maybe Halpert had stolen his car. Something like that. So the big fella pulls out a sock filled with nickels. Then Schrute grabs a can of hairspray and a lighter…”
— Creed
12. The Job (Season 3, Episodes 24-25)
The season 3 finale marked the end of the Stamford merger era and Jim’s relationship with Karen (Rashida Jones). As Michael, Jim, and Karen all travel to New York to interview with CFO David Wallace (Andy Buckley) for what turns out to be Jan’s position, Jim has a realization and returns to Scranton.
What prompted this about-face? A yogurt lid with an encouraging message from Pam (a callback to “Office Olympics”), as yogurt had become a recurring theme in the budding Jim-Pam romance (dating back to the pilot, when Jim noted Pam’s favorite flavor of yogurt). After two years and three seasons of Will They/Won’t They, “The Job’s” biggest surprise — besides Ryan getting the corporate job — was Jim finally asking the now-single Pam on a date.
“I am never, ever going to leave. I am going nowhere. This place is like the hospital where I was born, my house, my old age home, and my… graveyard. For my bones.”
— Michael
11. Fun Run (Season 4, Episodes 1-2)
By the time of “Fun Run,” Michael is enjoying “domestic bliss” with the recently laid-off Jan, “PB&J” are dating (in secret), and Ryan is working at corporate. The season 4 opener is best known for distracted driver Michael hitting Meredith (Kate Flannery) with his car in the parking lot, only to then assure the office that “everyone inside the car was fine.”
When Dwight reports to Michael that the hospital is giving Meredith the rabies vaccine following recent animal bites — a bat, a raccoon, and a rat — Michael decides to host a fun run race (Michael Scott’s Dunder Mifflin Scranton Meredith Palmer Memorial Celebrity Rabies Awareness Pro-Am Fun Run Race for the Cure) to raise awareness of the fact there is a cure for rabies.
“Guess what, I have flaws. What are they? Oh, I don’t know. I sing in the shower. Sometimes I spend too much time volunteering. Occasionally I’ll hit somebody with my car. So sue me. No, don’t sue me. That is the opposite of the point that I’m trying to make.”
— Michael
10. Goodbye, Michael (Season 7, Episode 22)
On Michael’s last day at the office before leaving for Colorado with fiancée Holly, he makes the rounds for his goodbyes: bear advice and paintball with Dwight, handmade mittens from Phyllis, gifts for Stanley and Andy (a ball-less felt and the company’s ten most important clients, respectively), a caricature for Kevin, and a crudely made doll for Oscar.
After a tearful goodbye in which Jim calls Michael “the best boss I ever had,” Michael leaves for the airport and almost misses Pam. “This is gonna feel so good, getting this thing off my chest,” Michael says, removing his mic. “That’s what she said.”
“The people that you work with are just, when you get down to it, your very best friends. They say on your deathbed, you never wish you spent more time at the office, but I will. Got to be a lot better than a deathbed. I actually don’t understand deathbeds. I mean, who would buy that?”
— Michael
9. Business School (Season 3, Episode 17)
A heartfelt Michael-Pam hug also ends “Business School,” where Ryan invites Michael to attend his Emerging Enterprises class as a guest speaker, and Pam invites the office to her art show. When a student lets slip that Ryan expects Dunder Mifflin to be obsolete in the next five to ten years due to competition from nationwide chains, Michael leaves the class in a huff — and later sends Ryan to the annex with Kelly.
“A good manager doesn’t fire people. He hires people and inspires people,” Michael says, imparting his final lesson. “People, Ryan. And people will never go out of business.” While Michael may not have been the best boss (despite the mug from Spencer Gifts), he was a good friend to Pam: after Oscar, Michael was the only coworker from the office to attend her art show, where he offered to buy Pam’s portrait of the office. Upon hanging it up on the wall opposite reception, Michael tells the camera: “Without paper, it could not have happened. Unless… you had a camera.”
“There are four kinds of business: Tourism. Food service. Railroads. And sales. And hospitals-slash-manufacturing. And air travel.”
— Michael
8. Booze Cruise (Season 2, Episode 11)
Although Michael may not be the most inspiring speaker, he did impart some advice to Jim during the office’s first quarter camaraderie event: a January booze cruise on Lake Wallenpaupack. “If you like her so much,” Michael told Jim of the long-engaged Pam, “don’t give up. Engaged ain’t married. Never, ever, ever give up.” (Amy Adams’ Katy was already a casualty of Jim’s crush on Pam.)
Taking the staff out of the office and trapping them on a booze cruise also makes for a great gag: while making a motivational analogy, Michael incites a panic when he tells the passengers the ship is sinking (causing one to jump overboard into the frozen lake).
“Last year, Michael’s theme was ‘Bowl over the Competition!’ So guess where we went.”
— Oscar
7. Finale (Season 9, Episodes 24-25)
Although The Office had declined by its Flanderized final season, the series finale (from pilot director Ken Kwapis and pilot writer Greg Daniels) had everything you could want from a final episode. Since the airing of the documentary, there were changes in the office (Kevin and Toby were fired, Stanley retired, a once-fired Devon was rehired). There was a wedding (Regional Manager Dwight marrying Angela at Schrute Farms). There was a big life change (Pam and Jim moving so he could work at Austin-based Athlead). And there were reunions (Michael Scott returning as Dwight’s best man for one last “that’s what she said”).
More emotional than funny, The Office finale ends with heartfelt exchanges before Pam — delivering the final line of the series — takes the painting of the office building down from the wall. “I thought it was weird when you picked us to make a documentary,” Pam says in her final confessional. “But all in all…I think an ordinary paper company like Dunder Mifflin was a great subject for a documentary. There’s a lot of beauty in ordinary things. Isn’t that kind of the point?”
“I wish there was a way to know you’re in the good old days before you’ve actually left them.”
— Andy
6. Casino Night (Season 2, Episode 22)
More romantic than comedic, “Casino Night” finds self-proclaimed “great philanderer” Michael caught between Jan and realtor Carol (Nancy Walls) when the warehouse is turned into a gambling hall for Scranton Business Park’s charity Casino Night. Besides a kleptomaniac Creed cleaning up, poker champion Kevin going all-in on losing to Phyllis, and a hilarious exchange about how Michael will donate the proceeds “to Afghanistanis with AIDS,” the episode includes a jaw-dropping confession:
“I’m in love with you,” Jim tells Pam, before a season-ending kiss leaves them both speechless. As Michael says of his own romantic troubles: “Love triangle. Drama.” Also, it gives us this oft-quoted classic:
“Why are you the way that you are? Honestly, every time I try to do something fun or exciting, you make it not that way. I hate so much about the things that you choose to be.”
— Michael to Toby
5. The Dundies (Season 2, Episode 1)
After its six-episode first season, The Office hit its stride with the Mindy Kaling-penned episode mostly set in a Chili’s. Michael hosts the annual employee awards night that hands out “Dundies” for such superlatives as “Busiest Bushiest Beaver” and “Hottest in the Office.”
During the cringeworthy ceremony, Michael Dundie-izes tracks like Naughty by Nature’s “O.P.P.” (“You down with the Dundies?”) and Elton John’s “Tiny Dancer” (“You have won a tiny Dundie”); Dwight botches his role as MC; and a drunken Pam excitedly kisses Jim when she wins the “Whitest Sneakers” award before being banned from the restaurant chain.
“You know what they say about a car wreck, where it’s so awful you can’t look away? The Dundies are like a car wreck that you want to look away… but you have to stare at it because your boss is making you.”
— Pam
4. Beach Games (Season 3, Episode 23)
The penultimate episode of season 3 is where the plots of the season come to a head: the Pam-Jim-Karen and Pam-Roy-Jim love triangles and the Scranton-Stamford merger, the result of which is Michael hosting a Survivor-style competition to determine his successor as Regional Manager of Dunder Mifflin Scranton.
Michael considers candidates Jim, Dwight, Stanley, and Andy (despite not yet having the corporate position). We get to see the staff battle it out (literally and figuratively) in a series of challenges, from inflatable sumo wrestling to a hotdog eating competition. In the end, an empowered Pam manages to speak up about her coworkers skipping her art show and her feelings for Jim after calling off her wedding to Roy.
“I would rather work for an upturned broom with a bucket for a head than work with somebody else in this office besides myself.”
— Stanley
3. The Injury (Season 2, Episode 12)
“The Injury” is one of the most accessible episodes of The Office. When Michael burns his foot by stepping on his George Foreman Grill, Dwight gets the more serious injury when he crashes his car into a pole while racing to Michael’s aid: a concussion.
Although jealous over the attention Dwight receives for his injury, Michael accompanies Dwight during his CAT scan (and tries to insert his foot in the machine). Plus, a concussed Dwight befriends Pam long before their actual friendship would develop.
“What do I write under ‘reason for visit’?”
“Concussion. What did you write?”
“Nothing. I wrote ‘bringing someone to the hospital.’”
— Michael and Jim
2. Stress Relief (Season 5, Episodes 14-15)
“Stress Relief” has, perhaps, one of the most memorable Office cold opens when safety officer Dwight — scorned over an ignored fire safety talk — sets fire to the office to demonstrate the proper procedure for exiting the building during an emergency.
All hell breaks loose: the trapped and panicked staff slams office equipment into doors and windows, cats are thrown into ceilings, Kevin raids a vending machine. After Dwight announces the simulation was a test of their emergency preparedness, Dwight’s drill leads to Stanley having a heart attack. Michael then takes it upon himself to make the office as peaceful a place as he can — only to cause Stanley even more stress.
“Nobody should have to go to work thinking, ‘Oh, this is the place that I might die today.’ That’s what a hospital is for. An office is for not dying. An office is a place to live life to the fullest, to the max. An office is a place where dreams come true.”
— Michael
1. Dinner Party (Season 4, Episode 13)
The arguably most quotable episode of The Office, babe, is also the cringiest. Michael invites couples Jim and Pam and Angela and Andy to dinner at his condo with Jan, but the night becomes — as Jim puts it — a game of “‘Let’s See How Uncomfortable We Can Make Our Guests.’”
And that goes for the audience: as Michael and Jan hash out their increasingly awkward anger issues during the excruciatingly long wait for dinner, there’s a spat over her candle-making business, Jan’s relationship with her former assistant turned singer-songwriter Hunter, the physical toll of Michael’s three vasectomies, and the death of Michael’s $200 plasma screen TV (appropriately destroyed with a Dundie). If you watch The Office for the awkward comedy, “Dinner Party” wins the Dundie for Cringiest. Episode. Ever.
“I would love to burn your candles!”
“You burn it, you buy it!”
“Oh, good. I’ll be your first customer!”
“You’re hardly my first!”
“THAT’S WHAT SHE SAID!”
— Michael and Jan
