21 Best Episodes of The Office

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Well, The Office is finally ending tonight after nine years on the air, at least two of which should probably never happened. I’ve been quietly saying goodbye ever since Steve Carell left near the end of the seventh season, but it doesn’t make the reality that there won’t be any more episodes that much easier to deal with.

As The Lord of the Rings did with movies, The Office might be the show that taught me how to appreciate television. I had a memorably insular childhood, only reading novels by Victorian writers. But then one night (one night!) during the summer of 2006, my best friends Booth and Corey invited me over to their place to watch this new show that seemed to be a documentary look at working life in the United States.

So The Office is inextricably bound up for me in those memories of being in college, of late nights and broken hearts, and those ominously quiet evenings during the snowstorm in 2007 when Booth and I stayed up in his room and watched the third season unfolding. It was through The Office that I reconnected with Bethany, who eagerly joined the two of us week after week as the Stamford branch merged with the Scranton branch, Andy Bernard wreaked havoc, and Michael Scott—my television hero—made a perpetual fool of himself.

Because, let’s face it, Steve Carell’s character was the heart and soul of The Office. I suspect that in one hundred years when students in film school want to know what genius looks like, their professors will dust off old recordings of his performance on this show because he illuminated just about every single scene he was in with his warmth, instinct for characterization, and effortless hilarity. This gift for creating a fully-developed character with all the subtleties of bodily expression was already evident in the second episode (“Diversity Day”), but it wasn’t until fifteen episodes later, in “Booze Cruise,” that it became obvious we were dealing with a comical behemoth, a true artist. Michael Scott is one of the greatest creations in the history of television, and perhaps of all comedy, and if he happens to make an appearance in tonight’s finale, I might reconsider my stance on these last two years of the show.

So, in that spirit, here are my twenty-one favorite episodes of The Office.

21. “Safety Training” (Season 3)

When Michael tries to draw the office’s attention to the dangers of work-related depression by jumping off the roof of the building onto a bouncy castle, Jim (John Krasinski) sums up the situation nicely: “He’s going to kill himself… by pretending to kill himself…”

20. “Health Care” (Season 1)

While Michael tries to find a surprise for the office, we get our first glimpse of Jim and Pam’s relationship with Dwight. “Count Choculitis? Why did you put that, Jim? Is it because you know I love Count Chocula?”

19. “Murder” (Season 6)

A surprisingly funny (and emotional) late-period Office, this episode centers around the relationship between Jim and Michael as the office is threatened with termination and Michael seeks to distract everyone with a murder mystery game.

18. “The Convict” (Season 3)

Not nearly as funny on repeat viewings, but the “Prison Mike” sequence is priceless.

17. “Dunder Mifflin Infinity” (Season 4)

Everyone hates on this episode, but watching it again I’m amazed at the number of now-classic moments per minute. Like many over-long Season 4 episodes, it only falls apart as it reaches the end.

 16. “Dinner Party” (Season 4)

The apotheosis of The Office’s darker fourth season, when it was on its way to becoming a nightmare comedy.

15. “Initiation” (Season 3)

Noteworthy if only for being the first appearance of Mose, this episode also features Michael at his zaniest. Probably The Office’s most representative episode.

14. “The Dundies” (Season 2)

Just a classic episode on all fronts, our first glimpse of the revamped Michael Scott, and the introduction of so many iconic Office elements.

13. “The Job” (Season 3, finale)

The show could have ended with this episode and it would have gone out flying.

12. “Conflict Resolution” (Season 2)

All the tensions that had been swirling in the office for two seasons came bubbling over in one golden half-hour.

11. “Drug Testing” (Season 2)

“NO! You told me when we came in here that I would be conducting the interview, now exactly HOW MUCH POT DID YOU SMOKE?!” Plus: Dwight in a hat!

10. “Ben Franklin” (Season 3)

Coming in the very middle of Season 3’s streak of near-perfect episodes, this one—in which Jim, assigned with the task of finding a stripper for Phyllis’s bachelorette party, hires a Ben Franklin impersonator—is hysterical and effortless. Season 2 gets a lot of praise, but in Season 3 the whole crew was working at the top of its game.

9. “Take Your Daughter to Work Day” (Season 2)

The show had worked hard to define Michael in the first couple of seasons, but this episode – and one moment, in particular – cemented his character forever.

8. “Goodbye, Michael” (Season 7)

The episode so honest, it felt like an actual goodbye. This is the only episode I refuse to watch again.

7. “A Benihana Christmas” (Season 3)

The merging of James Blunt’s music with Michael’s singing is so perfect, it’s hard to imagine one without the other. It remains the crowning moment in the greatest of all Office Christmases.

6. “Booze Cruise” (Season 2)

This has three of the greatest moments in the whole show – Michael trying to compete with the captain (“Iiiiiiii’m your party captain, TOO!”); Michael dancing; and Michael’s motivational speech (“This ship is sinking! And there aren’t enough spaces on the lifeboats!”).

5. “The Merger” (Season 3)

The Office’s first long episode feels a lot shorter than it is because it’s so packed with classic moments, among them the long-awaited first encounter between Andy and Michael, “Lazy Scranton,” Andy singing, “What is love? Baby don’t hurt me,” and Michael’s failed attempt to unite the office.

4. “Goodbye, Toby” (Season 4, finale)

There aren’t enough words to express how giddy this episode makes me, what with the first appearance of Holly and Michael singing (wailing, really), “Goodbye, Toby.”

 

3. “Product Recall” (Season 3)

Probably one of the show’s most underrated episodes, this one has two perfect story lines and the best cold opening the show ever did. “Bears. Beets. Battlestar Galactica!”

2. “The Injury” (Season 2)

From beginning to end, this might be The Office’s best half-hour. Billy Merchant’s speech in the conference room is a scene-stealer and everyone delivers fantastic performances (even Ryan, who is supposed to be dead).

1.      “Traveling Salesmen / The Return” (Season 3)

A great television show, like a great work of literature, is built from the infinite possibilities occasioned by the interactions between each of its characters. Regardless of the stylistic flourishes or structural brilliance, what really makes our most memorable examples of long-form storytelling memorable is their ability to create a whole cast of beloved characters, put them in a single room together, and watch the sparks fly.

“Traveling Salesmen / The Return” aired at a point in The Office’s history when the show was beginning to experiment with the template that over two and a half seasons had established it as the smartest and most inventive show on television. In the course of this season, one of the most perfect seasons in television comedy, it also attained a degree of reflectivity that was almost Shakespearean in the way it used mirroring characteristics and situations to create dramatic tension. (The lifting of an entire subplot from Twelfth Night in “The Convict” solidified this feeling that the show had gone beyond ordinary television to become a work of literature).

Never was this more intentional than during the series’ peak in the middle of Season 3 (what Oscar Dahl has called “a historic run of consistently great episodes”), where the love triangle between Pam / Jim / Roy and Pam / Jim / Karen meets the dueling ambitions embodied by Andy and Dwight as they struggle for Michael’s affections and, by extension, mastery of the office.

“Traveling Salesmen” tests and explores the relationships between each of these characters as they leave the office in pairs for a day of sales calls. Angela unexpectedly asks Pam out for coffee, Karen bonds with Phyllis and learns some surprising news about Jim’s past, Jim and Dwight are unstoppable, and Andy sets in motion a series of schemes that are intended to bring down Dwight. By the end of the episode, Dwight has been fired and Andy is now second-in-command in Scranton, thereby setting the stage for the absolute mayhem that is his brief run as assistant to the regional manager.

It all implodes in glorious fashion in the second half of this classic two-parter, as Jim, realizing how much he misses Dwight (“Congratulations, universe: you win”) teams up with Pam to play one of his best pranks, and Michael—being steadily driven insane by the only person in the office more irritating than himself—goes in search of the truth. When he finally faces off with Andy in front of the whole office, a timely phone call from Jim pushes our beloved usurper over the deep end in The Office’s most shocking moment.

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