
The concept of a documentary-style series that follows the regional branch of a paper-distribution company in Scranton, Pa., doesn’t sound like it’d amount to one of the most successful comedies of all-time. But fill it with excellently crafted characters, an incredible cast and some of the most intensely uncomfortable moments you’re likely to witness on television, and 15 years later, “The Office” is one of the most popular comedies in history.
At its best, the series manages to strike a balance between the extraordinary levels of awkwardness the workplace can foster, given the right circumstances, and a genuine earnestness about exploring people’s wants and desires. At its worst, it’s just not as iconic as you know it could be.
This list was not easy to compile, but if there’s one thing I learned, it’s that “The Office” absolutely follows the Michael Scott ethos: “Do I need to be liked? Absolutely not. I like to be liked, I enjoy being liked, I have to be liked, but it’s not like this compulsive need to be liked — like my need to be praised.” And let’s be frank, when it comes to this show, there’s more to praise than not.
Safety Training

Season 3, Episode 19
What’s more dangerous: a baler and a forklift or carpal tunnel and depression brought on by years of slogging it out in the hovels of corporate America? Michael Scott’s willing to throw himself off the roof of his office building — with only a bouncy house to break his fall — to prove it’s the latter. A fun episode to kick us off.
Garden Party

Season 8, Episode 4
Season 8 definitely hit some rough spots after Michael’s move to Colorado, but the “Garden Party” episode is a bright spot in the search for its footing. Though many begrudge the attempt to turn Andy into the new Michael, this episode in which he throws a party on Dwight’s farm to impress his parents makes you feel for him. James Spader’s profound speech as Robert California gives us one of the character’s stand-out scenes on the show — though nothing will top his “I’m the fucking lizard king” moment. Plus the one-two punch of Dwight taking his party-throwing cues from a fake book Jim created and Mose playing the valet with parking skills that take him, let’s say, off the beaten path, makes for a solid entry.
The Negotiation

Season 3, Episode 18
Michael learns the “art of negotiating” when he finds out Darryl makes almost as much money as he does. He decides to head to New York to convince Jan to give him a raise. Of course, he does this with zero tact, leveraging sex and his romantic relationship for a bigger paycheck. Ultimately, Jan ends up hand-holding him through the process, and we get another superb Carrell and Hardin scene. Delivering the drama this episode are Jim and Pam. After The Confession at the end of Season 2, it takes almost a full season for us to finally get the Roy and Jim confrontation we knew was coming, and it does not disappoint. When Roy shows up at the office ready to fight, Dwight steps in as the civilian hero and stops him with pepper spray. An enthusiastic “bippity boppity” for this episode.
Local Ad

Season 4, Episode 5
Michael’s title gets upgraded to “world’s most creative boss” when he takes it upon himself to shoot and produce the local commercial for Dunder Mifflin. The reaction shots of the corporate liaisons experiencing Michael in his glory for the first time are *chef’s kiss* and make for some of the episode’s funniest moments, but it’s the staff executing their respective assignments and breaking away from the day-to-day monotony that make this episode so much fun. From the Darryl-led jingle (“Dunder Mifflin, the people person’s paper people”) to Pam’s animation skills, the commercial gives them a rare chance to bring their personal interests to the conference room table.
Company Picnic

Season 5, Episode 28
This season finale marks some major changes for some of our characters, particularly Jim and Pam, who find out they’re expecting after Pam hurts her ankle playing volleyball at the company picnic. Michael is modestly chastened for once when he sees Holly is still with her boyfriend A.J., but the highlight of this episode is undoubtedly Holly and Michael’s intensely awkward “SlumDunder Mifflinaire” parody performance that accidentally reveals the Buffalo branch is closing. While Stanley’s the only one who sees the humor, it hints at the pair’s perfect match.
Golden Ticket

Season 5, Episode 19
Few people commit to a bit quite like Steve Carell playing Michael Scott. When Michael gets the urge to introduce a bit of “whimsy” into the lives of Dunder Mifflin’s clientele, he shows up in a purple velvet jacket, top hat and bowtie to kick off his Willy Wonka Golden Ticket promotional idea. As with many of Michael’s ideas, it backfires when all the tickets are sent to their biggest client. Dwight’s convinced to “fall on his sword” for his boss — a turning point for the assistant to the regional manager. Lucky for him, he’s spared in the end when the client makes Dunder Mifflin its sole office supplier, leading Michael to shamelessly claim back the credit. Not the best moment for Michael, but Willy Wonka wasn’t that great, either.
The Return

Season 3, Episode 13
The title of this episode references several comings and goings: Oscar is back from his monthslong settlement vacation after Michael kissed him in “Gay Witch Hunt,” a prematurely fired Dwight is allowed to return to his job after a stint at Staples and Jim brings Andy’s anger issues to a boil by hiding his cell phone in the ceiling. It’s a meaningful episode that deepens Dwight and Michael’s relationship and simultaneously confirms what we (and Karen) already knew: Jim still has feelings for Pam and adding accents to random letters doesn’t make “lemoñadé” any more Mexican.
Gay Witch Hunt

Season 3, Episode 1
Featuring the unscripted kiss seen round the world, this episode is one that helped solidify Carell’s status as a comedic juggernaut. When Oscar’s outed as gay, the various responses are what drive this episode forward. While it marked an elevation in risk-taking for the acting, the writing never fully gives Oscar his own equivalent of Kelly slapping Michael in the “Diversity Day” episode, making this one that falls short of its potential. However, the arc of Jim’s move to Stamford after Pam’s rejection is kicked off beautifully with coupled shots of both looking at the empty chairs next to them in their respective new offices. It hurts so good.
The Convict

Season 3, Episode 9
One of the most memorable of Carell’s performances on the series, his Prison Mike has inspired T-shirts, magnets, candles, stickers and more featuring the actor’s scrunched face in a purple bandana. One of the new Stamford transfers is discovered to be a former felon, and the mere suggestion that prison is better than the drudgery of office life combines with Michael’s unadulterated love for Dunder Mifflin to spectacular effect. His scheme to scare everyone straight devolves into talk of “dementors” in “the clink” and Michael attempting to imprison everyone in the conference room. It’s one of the more cringe-inducing conference-room scenes, but one that manages to root the comedy in Michael’s delusions about the world rather than “punching down” at someone’s reality — an achievement that doesn’t always happen on the show.
The Dundies

Season 2, Episode 1
One of the few times Michael exhibits any real sense of self-awareness comes when he realizes most of his jokes probably won’t be funny after Jan and a tight budget kill the open bar at the company’s annual “awards ceremony.” “There’s a reason there’s a two-drink minimum at a comedy club!” he exclaims. We get to see some great sound mixing from Dwight, an inebriated Pam and a rare moment of unified support for Michael after a heckler butts in. (He’s an idiot, but he’s their idiot.) In a pivotal move for Pam — Fischer really does play an impeccable drunk here — she chooses to stay and hang with Jim instead of going home with Roy. While some of the jokes and awards really haven’t aged well, it remains a standout episode for cast performances.
Office Olympics

Season 2, Episode 3
Few things unite the employees of Dunder Mifflin quite like procrastination. The perfect opportunity presents itself when Dwight goes with Michael to help sign the closing papers on his new condo while the rest of the group combine their favorite office games to create the Office Olympics — complete with an opening ceremony and medals made of paper clips and yogurt lids. Games include racing while holding a full cup of coffee, guessing who’s coming up the elevator and seeing how many M&Ms Kevin can fit in his mouth. The emotional payoff comes at the end when the other “athletes” honor Michael’s homeowner achievement in the closing ceremonies and a soft-hearted Jim hangs on to the medal Pam made for him.
Threat Level Midnight

Season 7, Episode 17
What could have been a throwaway concept introduced five seasons ago pays dividends when we finally see the premiere of Michael’s magnum opus, the feature film 10 years in the making, “Threat Level Midnight.” There are too many good moments to name, but highlights include the simple joy of great actors acting very badly, Dwight’s creative liberties as the robot butler, Jim in costume as Golden Face — with glitter that stops at his neck — the classic line, “Go puck yourself,” and of course, the “most expensive” shot of the whole film: Michael cinematically killing Toby by blowing up his head about six times over.
Goodbye, Toby

Season 4, Episode 14
“If the devil were to explode and evil were gone forever, what kind of party would you have?” Well, in this case, there’s a parking lot, a Ferris wheel and a bad parody song. “The Office” has made much hay of several running gags over the series’ run, and Michael’s bold-faced hatred for HR representative Toby Flenderson is one of its best. So it’s no surprise that when Toby announces he’s moving to Costa Rica, Michael throws an elaborate going-away party (much of which is paid for with money from his senile grandmother). It’s a jam-packed episode that introduces the future Mrs. Scott, Holly Flax, and pregnant Jan, who would rather go to a sperm bank than give Michael a shot at one of her kids. Plus, Andy’s proposal (and a very unenthusiastic “OK” from Angela) derails Jim’s first attempt at a marriage proposal. A solid season finale.
Niagara: Part 1 & 2

Season 6, Episode 4–5
“I know way too much about Andy’s scrotum,” is the spirit behind this double header following Jim and Pam’s wedding party. While it’s a feel-good episode that lets the entire cast shine, watching it now feels a bit like opening a 2009 time capsule that includes the very real YouTube trend of people dancing down the aisle at weddings and the 2007 Chris Brown hit “Forever” — both come together to create a very specific blend of nuptial hell and comedic bliss. We love to see it.
Money

Season 4, Episode 4
Storylines set outside of the office are always a risk, but they usually mean we’re about to get to know one of the employees a bit better — and honestly, this episode explains a lot. For one, Jim and Pam learn more about Dwight and Cousin Mose than they bargained for after they spend a night at their “agritourism” bed and breakfast on Schrute Farm. (Activities including manure spreading, a table-making demonstration and, of course, making beet wine.) We also find out Michael’s taken on a second job in telemarketing selling diet pills to be able to afford Jan’s spending habits. On Oscar’s recommendation, he decides to declare bankruptcy by literally announcing “I declare bankruptcy” to the entire office. Despite it being one of the hourlongs, “Money” excels as one of the leaner extended installments.
Diversity Day

Season 1, Episode 2
If there was any worry about the U.S. version of the U.K. “Office” shying away from David Brent’s nearly unconscionable ignorance, the second-ever episode put those doubts to rest. When corporate sends Mr. Brown (Larry Wilmore) to teach the entire office about respecting those from different backgrounds, Michael kicks us off on an inappropriate note, asking everyone to share a race they’re sexually attracted to. When corporate’s methods don’t deliver Michael the “Oprah moment” he was hoping for, he decides to lead his own Diversity Day that culminates in Kelly slapping him across the face for an offensive Indian accent. While it’s one of the extremely non-PC episodes of “The Office” that makes people wonder if the show would be able to exist in the same form on television today, Kelly’s slap at the very least shows consequences for Michael and awareness from the writers.
The Deposition

Season 4, Episode 8
Michael plays the pawn in Jan’s scheme to sue the company for discriminatory termination after her breast augmentation. At first things seem to be going well with Michael sticking to the very specific script he was fed prior to the meeting, outlining the nature and timeline of their relationship. But when Michael’s honesty and ill-timed “that’s what she said” jokes bungle it all, we see just how far Jan’s willing to go to try and Scott-proof this deposition, including entering his personal diary into evidence. (The fact that his diary wasn’t used more on the show is criminal.) Melora Hardin as Jan is brilliant playing the straight-arrow foil to Michael’s antics, and their onscreen dynamic is one of the show’s best.
Fun Run

Season 4, Episode 1
After Michael hits Meredith with his car, sending her to the hospital with a cracked pelvis, the entire office is shocked and disappointed at his carelessness. Since there’s nothing he hates more than being the bad guy, he uses Meredith’s unrelated rabies diagnosis to try and redeem himself with his co-workers via a charitable 5k run. Michael Scott’s Dunder Mifflin Scranton Meredith Palmer Memorial Celebrity Rabies Awareness Pro-Am Fun Run Race For the Cure will live forever thanks to Season 4.
Beach Games

Season 3, Episode 23
A quintessential “Office” episode that drops the group into a scenario that perfectly tugs at its dynamics. When Michael thinks he might land the job in New York, he puts together a dinky “Survivor”-esque series of challenges to determine who is worthy of being his successor. Pam, not even a consideration for Michael, is designated note-taker for the day while the rest of the employees don absurd sumo suits to wrestle it out, walk across hot coals and race each other blindfolded. Both the Dwight-Andy-Angela and Jim-Pam-Karen love triangles play heavily here, and the latter makes space for a moving monologue from Pam — a great moment for Fischer on the series.
The Job

Season 3, Episode 23
This is hands down the Rainn Wilson show when Dwight gets to live his wildest dream of becoming the regional manager of the Scranton branch for a day. The rest of the cast also deliver in this episode that sees Jim, Karen and Michael interview for the corporate job in New York. In true Dwight fashion, he paints his office pitch black and instills Schrute bucks as in-office motivational tools (1,000 Schrute bucks get you an extra five minutes for lunch). Jan gets fired from her job, but the real kicker comes at the very end when Jim asks Pam out to dinner, leaving us with another cliffhanger that’s not quite as hefty as its predecessor, but does the job.
Finale

Season 9, Episode 24–25
Nine seasons of ups and downs and “The Office” finale is an unabated high. Closing out any series is a feat, but as is always the case for the most successful parts of the show, the writers lean into the rock-solid characters and character relationships we watched grow over years to properly cap off the series. Dwight, Pam and Jim’s friendship is a thing to behold and we even get a perfectly placed “that’s what she said” from a returning Michael Scott. While not everyone gets a happy ending — the law finally catches up with Creed, Toby’s living with six roommates and Phyllis really misses Stanley — we all got the ending we deserved.
Gossip

Season 6, Episode 1
The “parkour” cold open of this Season 6 starter alone is enough to push it toward the top of any best-of “The Office” list. But the rumors — each perfectly tailored to the show’s personalities — that Michael starts, to diffuse the truth about Stanley’s affair, make for some top-notch interactions. Angela’s dating an 81-year-old billionaire. Oscar voiced the Taco Bell dog. Creed has asthma. Jim and Pam are pregnant, which is actually true at this point. As usual, Michael’s intentions are in the right place, even if his attempts to fix his mistakes are painfully misguided.
Broke

Season 5, Episode 25
When the rival Michael Scott Paper Company begins to cut into Dunder Mifflin’s core business by undercutting their prices, upper management goes into damage control mode, with no idea that its competitor is going broke thanks to their steep discounts. With Jim’s help positing Pam, Ryan and Michael as “titans of the industry” and a strict code of silence about the company’s financials, they land a buyout offer. In a stunning display of restraint and composure, Michael manages to strongarm the company into reinstating all three of their positions, giving the character a needed win and hinting at a modicum of personal growth.
The Injury

Season 2, Episode 12
Imagine loving the smell of bacon first thing in the morning so much that you’d be willing to sleep next to a George Foreman grill to get it. Nearing the end of Season 2, we’re really beginning to understand the caricature of narcissism that is Michael Scott, and “The Injury,” in which he sears his foot on the aforementioned grill, stands as one of his most ridiculous displays to date. From trying to piggyback on Dwight’s concussion CAT scan to asking Pam to rub Country Crock on his burn — Michael’s near-obscene lack of self-awareness creates many opportunities for Carell to milk this bubble-wrapped situation for all its worth. And milk he does.
Garage Sale

Season 7, Episode 19
A few episodes of “The Office” really land the delicate balance between LOL moments and heartfelt payoffs, and this is one of them. While most of the Scranton branch is occupied selling their stuff at the company’s charity garage sale, Pam, Jim, Oscar and Ryan try to talk Michael into the least destructive, strange or off-putting proposal idea for Holly after Pam finds him in the parking lot trying to write “Will you marry me?” in gasoline. The final idea still turns out to be a fire hazard, but the Yoda-voiced marriage proposal and acceptance is perfection. It also sets the stage for Carell’s imminent departure when Michael announces he’s moving to Colorado with his new fiancée.
Business School

Season 3, Episode 16
Ryan will make several very questionable decisions throughout the course of the show, but inviting Michael to be the guest speaker for his business class is right up there with getting arrested for fraud in Season 4. Compelled by the offer of a full-letter grade increase, Ryan gifts Michael (and us) with the perfect stage to showcase how little Dunder Mifflin’s regional manager actually knows about running a modern-day paper-distribution branch. And damn, does Michael deliver, highlighting yet again that his successes are more often than not thanks to his tendency to fall ass-backwards into a lucky situation. That said, his unforgettable presentation incorporating candy bars, which he later hurls at a group of students, is a great tactic from where I’m sitting; them, not so much.
Goodbye, Michael

Season 7, Episode 21
The one where we bid adieu to the world’s best boss and the show’s major anchor. Once Michael makes the decision to leave with Holly, the Scranton branch and “The Office” must go on without him. The writers will spend a good portion of the next two seasons trying to fill the gaping hole Carell leaves behind, but at least they send him off right. Clocking in as one of the more emotional episodes of the series, it’s a lasting fan favorite that serves the laughs, gut-wrenching goodbyes and much-needed catharsis to rightfully mark the end of an era. Michael captures our feelings perfectly: “They say on your deathbed, you never wish you spent more time at the office, but I will. Gotta be a lot better than a deathbed.”
Casino Night

Season 2, Episode 22
Season 2 culminates in one of the series’ most crucial moments — one of maybe four biggies the writers really couldn’t afford to screw up: Jim confessing he’s in love with Pam to her face. Forty-odd episodes worth of will-they-won’t-they inside jokes and flirting come to a head in the parking lot outside of the company’s charity fundraiser. We get some gutsy dramatic performances from both John Krasinski (Jim’s lone, cascading tear!) and Jenna Fischer (Pam’s initial shock moves heartbreakingly to sadness) ahead of one of TV history’s most gratifying first kisses. Meanwhile, the rest of the cast provides some great side moments at a very illegal casino night: gambling enthusiast Kevin losing to the casual novice Phyllis, Toby learning the joys of taking money from Michael and Michael dealing with the complications of inviting two dates to the same event.
Stress Relief

Season 5, Episode 13
A major strength of “The Office” has always been its ability to tease out ingrained character responses that make you go, that’s so Creed! Or Michael. Or Kelly. And they really up the ante with some life-or-death stakes when Dwight hatches an elaborate plan to teach fire safety protocol by starting a small blaze in the building and ultimately giving Stanley a heart attack. Watching each character play out a perfectly written, if chaotic, fight-or-flight instinct is nothing short of first-rate: Angela pulls a cat out of a filing cabinet drawer, Michael throws a printer out the window and screams for help, and Jim’s mostly focused on getting Pam out of the building. Some of the show’s most iconic moments also happen in this episode — from Dwight cutting the face off a CPR doll à la Hannibal Lecter to the staff’s backup vocals for the Bee Gees’ “Stayin’ Alive” training song. “Stress Relief” is a masterful blend of physicality and comedic timing that the entire cast nails.
The Dinner Party

Season 4, Episode 13
This episode is what happens when you give geniuses the chance to play peak cringe-comedy. As the evening’s planned events unfold — dinner, charades and a tour of Jan’s at-home candle business — we peel back the layers of dysfunction in Michael and Jan’s relationship. Initially, the writers were worried it was too dark and asked Carell to lighten it up a bit, leading to the brilliant “Snip, snap! Snip, snap!” description of his multiple vasectomies. “Dinner Party” features some of the most hilarious scenes of the entire series, including Michael showing off his tiny plasma TV in one of the best uses of a pan-out ever, Jan dancing with Jim’s limp arm and Michael describing his wine as having “an oaky afterbirth.” It’s all so squirm-inducing, that by the end, it feels like we’ve been stewing in the discomfort for as long as Jan’s osso buco.
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