20 Best Episodes of The Office

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On May 16, audiences will watch as the Scranton, Penn.-based employees of Dunder-Mifflin close up the office for the last time.

It’s certainly been an interesting journey for a show that spent its first season living in the shadow of its critically adored British predecessor only to grow into one of the most beloved (and highest rated) American sitcoms of the 2000s. And while its quality might have fluctuated over the years, few will deny that the end of The Office marks the end of an era.

It’s the show that turned Steve Carell into a comedy superstar, enlisted the talents of such high-profile directors as J.J. Abrams, Harold Ramis, Jon Favreau and Joss Whedon and turned the “mockumentary” model into a viable TV structure, paving the way for shows like Modern Family and Parks and Recreation.

In honor of the show’s upcoming series finale, we take a look at some of the major highlights from the show’s nine years on the air. With close to 200 episodes, witling a list down to 20 is no easy task. Nevertheless, here are the episodes that truly defined the best that the show had to offer.

20. Threat Level Midnight
Season 7, Episode 17
Why It’s Great: With Michael Scott’s departure from the office fast approaching, the writers decided to take a trip down memory lane. “Threat Level Midnight,” is a concept seeded by an episode back in Season Two where the office finds Michael’s script for an action film. The episode allowed the writers to break the mold of traditional Office episodes, introducing a genre parody to rival Community (which, incidentally, ran an Office-style, faux documentary episode that same night). Moreover, since Michael’s film was shot and edited over the course of many years, the structure allows the audience to bring back former recurring characters in small cameos, including Karen, Roy and Jan.

19. Diwali
Season 3, Episode 6
Why It’s Great: Being that he’s as culturally insensitive as he is well-meaning, placing Michael at a Diwali celebration would be a firm foundation by itself for a funny episode. In the hands of writer/Kelly Kapoor Mindy Kaling, however, you have both a strong collection of ensemble character bits as well as an ideal example of what could happen when the creators take the action outside the office setting. This half-hour is full of comedic gems, whether it’s Michael mistaking the ceremony for a Halloween party or Ryan being hit on by Kelly’s relatives. Yet it also contains some of the most cringe-worthy elements of the series; namely, when Michael makes an ill-advised proposal to Carol in front of everyone and then later tries to kiss Pam after she shows him a bit of compassion.

18. Niagara
Season 6, Episode 4/5
Why It’s Great: Jim and Pam’s relationship has always been the heart of the The Office. For six seasons, we witnessed as they evolved from flirtatious office mates to a serious item to husband and wife and, finally, to parents of two children. “Niagara” signals a major touchstone in the relationship: the wedding. Despite the fact that the hour-long episode feels a tad overstuffed at times, the proper poignancy is there in spades. Even the remake of the YouTube video involving a wedding march to Chris Brown’s “Forever” manages to transcend its inherent cheesiness and become quite the heart-warmer.

17. Garage Sale
Season 7, Episode 19
Why It’s Great: If ever there were any moment on the show that could rival the exuberant sweetness that was Jim and Pam’s wedding, it would be Michael’s candle-lit proposal to Holly (complete with Yoda impersonations). Since first introduced in the fourth season finale, Holly (played brilliantly by Oscar-nominee Amy Ryan) has served as Michael’s white whale—the woman both he and the audience knew was his destined soulmate. After years of ill-timing, however, Michael finally found himself with the woman he was always meant to be with. Moreover, those two and half seasons of build-up make “Garage Sale” all the more inspiring. The only damper on the party? Michael immediately announces after the engagement that he’ll be leaving the Scranton office (but we’ll get to that later).

16. Diversity Day
Season 1, Episode 2
Why It’s Great: The Office gets a lot of flack for its lackluster first season. Yet, for all its issues, there were certainly moments in its inaugural episodes that would point towards its potential for greatness. After the line-by-line remake of the original’s pilot episode, “Diversity Day” started pushing the characters away from their British counterparts. And while those characters aren’t yet solid, “Diversity Day” is if nothing else a hilarious rough draft in how the show would craft its brand of cringe humor, especially with Michael’s woeful handling of the racial sensitivity activities.

15. The Merger
Season 3, Episode 8
Why It’s Great: Being that The Office began its run with the Scranton employees already somewhat used to Michael’s personality and highjinks, “The Merger” served as an excellent outlet for pitting Michael against Dunder-Mifflin workers not accustomed to his unique brand of management. The outlet in question is the incorporation of the defunct Samford branch into the Scranton branch. While some of the new employees simply smile politely and accept Michael’s eccentric nature, others take off before the episode is even done. Eventually, by the end of Season Three, Andy would be the only Samford transfer left standing.

14.The Duel
Season 5, Episode 12
Why It’s Great: For all the complaints about Michael’s ever-shifting personality, perhaps no character has had a more schizophrenic characterization than Andy Bernard. Beginning as an obnoxious brown-noser with anger issues, the writers softened Andy’s edges in subsequent seasons only to bring it back in this recent season. “The Duel” did wonders in fleshing out the Nard-Dog, allowing him to be play a sympathetic role after being the clueless cuckold oblivious to Dwight and Angela’s affair (for a comedically long period, I might add).

On another note, a subplot features Michael traveling to Dunder-Mifflin headquarters and being asked by his boss how exactly his branch has been so successful in the wake of economic devastation. After countless episodes of Michael being humiliated, belittled or committing numerous faux pas, it’s refreshing to see a moment where his actions are praised…even if he doesn’t quite know how entirely how to handle it.

13. Halloween
Season 2, Episode 5
Why It’s Great: The Office could always be relied upon when it came to producing funny Halloween episodes. This first one set the template, with the added drama of Michael having to fire an employee by day’s end. Simply the image of a man like Michael struggling with a major, anxiety-laden decision while sprouting a paper mache head on his shoulder is comedy gold on its own. Not to mention, this episode is the first to introduce us to the hilarious scene-stealing antics of office weirdo Creed. What further solidifies this episode as one of the greats, however, is the final montage. As Michael laughs about the numerous hilarious costumes he’s donned in the past during a voiceover, we watch as a much more isolated and lonely Michael picks up the office, cleans his car (the fired employee had dropped a pumpkin on it) and drives back to an empty house. This juxtaposition serves as a fine example of the emotional impact that the show could muster with only a few choice images and some great writing.

12. The Deposition
Season 4, Episode 8
Why It’s Great:When she first appeared on screen as the corporate tightass in Season Two, few could have predicted that Jan Levinson would become the worst thing that ever happened to Michael. “The Deposition” plays as much as psychological warfare as it does as comedy, with Jan forcing Michael to testify against his beloved Dunder-Mifflin as part of her wrongful termination lawsuit. Things get complicated, however, when the company reveals facts about Jan’s past actions that has Michael rethinking his position. It’s a brutal episode, but one that would ultimately serve as but the prelude for the storm to come. Perhaps to balance the darkness of the main plot, a subplot has Daryl and Jim participating in a friendly game of ping pong that their respective girlfriends (Kelly and Pam) turn into a competition.

11. Launch Party
Season 4, Episode 3
Why It’s Great: Season 4 began with a series of hour-long episodes that effectively derailed the series with its padded plotlines and half-baked situations. The gem of these episodes, however, is “Launch Party.” Unlike other installments, “Launch Party” is full of enough memorable plotlines to successful fill the hour mark. Michael abducts a pizza delivery guy after learning he’s been cut from the Dunder-Mifflin launch party, Dwight attempts to prove his worthiness to Angela by selling more paper than Dunder-Mifflin’s new computer program and Andy’s wooing of Angela culminates with a conference call performance of ABBA’s “Take a Chance on Me.” It’s fun all around and served to placate fans who no doubt worried that The Office had lost its direction.

On May 16, audiences will watch as the Scranton, Penn.-based employees of Dunder-Mifflin close up the office for the last time.

In honor of the show’s upcoming series finale, we take a look at some of the major highlights from the show’s nine years on the air. With close to 200 episodes, witling a list down to 20 is no easy task. Nevertheless, here are the episodes that truly defined the best that the show had to offer.

10. Dwight’s Speech
Season 2, Episode 17
Why It’s Great: This…

9. The Dundies
Season 2, Episode 1
Why It’s Great: After the rough patch that was the first season, The Office came into it’s own in a very big way with “The Dundies.” The episode centers on Michael preparing to host the annual office awards show, The Dundies. This year, unfortunately, he discovers that the company will not be able to pay for food or drinks. Things get worse when, during the ceremony, he must face a disinterested crowd and hecklers who dismiss his act. Whereas the episode could have taken a simple route and honed exclusively on Michael’s embarrassing failings as an MC, it manages a perfect balance between drawing laughter from his misfortunate while also serving as a lovely portrait of how his office mates have become a supportive, surrogate family. And, of course, let’s not forget that this episode introduced us to the glory that is Drunk Pam.

8. Booze Cruise
Season 2, Episode 11
Why It’s Great: Airing midway through the second season, “Booze Cruise” stands as one of the most perfectly structured and executed Office episodes, featuring both hilariously inappropriate behavior from Michael as well as a healthy does of heart as evidenced by Jim confiding in Michael about his crush on Pam. Granted, Michael couldn’t hold that secret back for long but it made for a touching scene nonetheless. The one downside? This would mark the final appearance of Amy Adams as Jim’s girlfriend Katy.

7. The Job
Season 3, Episode 23
Why It’s Great: After nine seasons, “The Job” remains one of the funniest and most emotionally satisfying season finales the show has ever produced. The episode has Michael, Jim and Karen traveling to New York in order to interview for a new corporate job that has just opened up. Michael’s confidence in gaining the job goes south, however, once he realizes that he would be replacing his girlfriend Jan (who is unaware that she’s being fired). The insanity at corporate is paralleled by the insanity back at the office where Dwight, after three seasons of trying to amass as much power as possible, becomes the temporary Regional Manager. He even goes so far as to paint his “office” black in order to instill fear in other employees. Yet, undoubtedly, the show’s biggest moment is when Jim, in a scene reminiscent of the series finale of the original British Office, realizes how Pam has been a constant support for him throughout their time together. He then travels back to Scranton and, interrupting Pam’s talking-head interview, asks her out to dinner. The look on excitement on Pam’s face as he leaves the room is the perfect end note to what had been an almost perfect season.

6. Goodbye Michael
Season 7, Episode 20
Why It’s Great: While one can blame the writers for Michael Scott’s fickle character, few will argue that Steve Carell’s adept ability at capturing both the hateful and lovable sides of Michael was anything less than extraordinary. For their part, the writers were no doubt well-aware of the monumental emotional weight of this episode and delivered a fantastic send-off to one of the most unorthodox leading men of the 2000s. The story takes place the day before Michael will depart Scranton to live with future bride Holly in Boulder. What the office doesn’t know is that Michael will actually be leaving at the end of the day. Michael explains that the white lie is meant to avoid the painful, emotional farewell that would inevitably occur. And so, Michael spends the rest of the day subtly bidding adieu to his employees. As the day winds to a close, however, Michael finds it harder and harder to keep his composure. Steve Carrell has said he will not return for The Office’s final season, citing that he felt his character had made his proper exit. Watching this episode, you certainly see where he’s coming from.

5. Dinner Party
Season 4, Episode 9
Why It’s Great: Early on, the show established that it wouldn’t probe the dark, depressing depths seen in the original British version. If ever a single episode came close to matching the cringe-worthy feel of that Ricky Gervais-Stephen Merchant show, however, it was “Dinner Party.” The episode is an exercise in discomfort, with Jim, Pam, Angela and Andy attending a couple’s dinner at the home of Michael and Jan. Still on edge after the events of “The Deposition” Michael and Jan’s amiable façade almost instantly crumbles and their guests become witnesses to their explosive break up.

Overall, it’s a hell of an episode, even if you look like this while watching it.

4. Gay Witch Hunt
Season 3, Episode 1
Why It’s Great: If the Season Two opener “The Dundies” provided a major course-correction for the series, then the season three premiere, “Gay Witch Hunt,” solidified the incredible progress the show had made, launching what stands (arguably) as The Office’s best season. The episode begins with Michael inadvertently directing a homophobic comment at Oscar. Upon learning that Oscar is gay, an embarrassed Michael attempts to make it up to him by holding an ill-advised sensitivity seminar and, in one of the show’s most memorable unscripted moments, kissing Oscar on the lips. It’s a gut-busting episode that also features the introduction of recurring character Karen Fillippelli, played by Rashida Jones, and future main character/post-Michael Scott manager Andy Bernard.

3. Business School
Season 3, Episode 16
Why It’s Great: “Business School” might not contain a major event or serve as a great vehicle for a particular character. What it is, however, is a perfect summation for why, at the height of its creative power, The Office was one of the best shows on TV. The episode finds Michael traveling to Ryan’s business school to make a presentation. Thinking he will inspire the students, Michael instead finds himself humiliated and called obsolete. Elsewhere, Pam finally secures a gallery for her art, only to find hat none of her co-workers (or her fiancée Roy) are particularly interested. These stories expertly demonstrate how, at its best, the show excelled at drawing hilarious moments that were inexorably tied to a sense of sadness and melancholy. What gives the episode its true kick, however, is the final scene where Michael arrives at Pam’s deserted art show and conveys genuine interest in her paintings, even going so far as to pay for one. Having spent most of the episode feeling abandoned and isolated, an emotional Pam embraces him. It’s a small, quiet moment, but one that stands among the most heartwarming. And, just so things don’t get too mawkish, an unfortunately placed Chunky Bar in Michael’s pocket effectively diffuses the moment.

Oh, and just in case you needed more proof that this episode was helmed by Buffy the Vampire Slayer scribe Joss Whedon, a subplot involves a bat being let loose in the office and Jim, knowing Dwight’s nature, pretending like a bit from the bat is turning him into a vampire.

2. The Injury
Season 2, Episode 12
Why It’s Great:“The Injury” begins with bang, boasting perhaps the funniest cold opening in the show’s history. Michael calls the office in “agony” having burned his foot on his George Foreman grill. This prompts Dwight to rush to assist him in his car, only to crash into an electric pole, vomit and continue onward. While the rest of the episode features Michael at perhaps his most self-centered and insensitive. Dwight takes the exact opposite direction. As a result of the concussion stemming from his accident, he starts acting more cordial and friendly to his office mates. It’s a wonderful change of character that truly gives Rainn Wilson a chance to show off his range as an actor.

1. Casino Night
Season 2, Episode 22
Why It’s Great: Because Jim finally tells Pam he loves her, of course. But seriously, the episode, with a script courtesy of star Steve Carell, contains countless inspired bits, not the least of which is the introduction of Kevin’s Police tribute band Scrantonicity. Ultimately though, it all comes down to those final five minutes and Jim’s tearful confession, which is only intensified in the final shot where Jim wordlessly approaches Pam in the office and kisses her. Even knowing that the couple would pull through and make good, “Casino Night” remains a haunting and incredible episode of television.

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