The Ten Best THE OFFICE Episodes of Season Two

Welcome to a new Sitcom Tuesday! This week, I’m continuing my coverage of The Office (2005-2013, NBC), which is currently available on DVD and Peacock. Please note that for these posts, I watched and will be considering the regular version of the show that presently appears on cable and online — with 204 half-hour episodes total.

The Office stars STEVE CARELL as Michael Scott, RAINN WILSON as Dwight K. Schrute, JOHN KRASINSKI as Jim Halpert, JENNA FISCHER as Pam Beesly, and B.J. NOVAK as Ryan Howard. See more of the regular ensemble cast here.

A sitcom is usually at its best when a falling novelty of premise intersects with a rising knowledge of the characters. Although The Office is basically just a low-concept ensemble workplace comedy, its high-concept mockumentary framing, evidenced best through so-called “cringe” comedy, constitutes a crucial part of the situation that defines so much of its identity and therefore must be well-featured. Also, because its storytelling reflects a heavy rom-com bent, the show can’t help but reiterate the genre’s oft-proved notion that “will they? won’t they?” angst is more narratively exciting than what tends to come after: forced obstacles that toil to complicate an inevitable pairing or challenge an otherwise happy status quo. Accordingly, The Office is most primed for self-defined greatness here in Two; this is when it’s still new enough to excite on behalf of key conceptual tenets that also feel well-invoked because they’re fresh (and don’t have to be forced), and with support from an already well-cultivated understanding of the leads, who uphold all parts of the situation in story. Michael Scott, in particular, has refined considerably from Season One, pivoting out of David Brent’s coarseness into a more likable figure who is better suited to American tastes and allows for the kind of emotional access necessary to sustain a long run’s narrative demands. Specifically, Michael develops an enhanced vulnerability via more congenial relationships with his staff, and some romantic pursuits that cement his desire to be loved, thereby rendering his obnoxious qualities either sympathetic and/or harmless. And since all aspects of the premise revolve around him and are projected through his comedy, Michael’s evolution evolves the entire tone of the show, making it more emotionally open as well. This shift maybe feels a bit heavy-handed at the top of Two, but the season seems to “get” Michael right away, and he, along with the other three main leads, have a good year as a result of these tweaks. Yes, the peripheral ensemble is still being fleshed out — they become more supportive later (stay tuned) — but all the main ingredients are already getting deployed with regular excellence, and in fact, I like all 22 episodes from Two (which won the show its only Outstanding Comedy Series Emmy), for its high baseline exhibits the situation with remarkable skill and humor, confirming The Office to be one of the best sitcoms of the 2000s.

 

01) Episode 7: “The Dundies” (Aired: 09/20/05)

Michael hosts an award show for his staff.

Written by Mindy Kaling | Directed by Greg Daniels

Season Two opens with a gem that showcases the revised Michael Scott, proving that the series has already learned so much from One, boasting a better handle on its characters and how to best feature them. “The Dundies” starts with a smart story, of Michael throwing his annual awards show for the office, and it’s a terrific display of his centralized characterization, for he tries to entertain both his staff and the cameras, unaware of how he’s making both them and us feel. That’s cringe comedy at its finest, beautifully highlighting the important mockumentary aspect of the premise, along with his increasingly affable persona as someone who just wants to be loved. Also, Pam’s decision to indulge Michael with her own enthusiasm is the beginning of their special rapport — where she recognizes his positive qualities and enjoys some of his goofiness — and it’s one of several times in early Two that either she or Jim (the two “normal” leads) sanction his character and give the audience permission to like him as well. So, this is a vital showing for Michael and the series at large, and with plenty of Jim/Pam rom-com stuff setting their course for the rest of the run, “The Dundies” is a classic. An MVE contender.

02) Episode 13: “The Client” (Aired: 11/08/05)

Michael and his boss Jan attempt to make a big sale.

Written by Paul Lieberstein | Directed by Greg Daniels

Another way that Season Two adds depth to Michael’s character is by playing into the show’s already well-founded rom-com ethos and giving him some love interests — one of which is the recurring Jan (Melora Hardin), his no-nonsense boss. She’s a fine match for Michael because they’re such a contrast, and this installment is the first great example of what their pairing can offer, as they hook up after a sales call. Their scenes are funny and character-revealing, and Michael’s success with both the client (Tim Meadows) and Jan makes it easier to root for him by proving that he does have an underdog, idiot savant-like charm. Meanwhile, the office relaxes while he’s away, as Pam finds Michael’s screenplay and the staff reads it aloud — an amusing notion that’ll be revisited in Michael Scott’s Farewell Season, but without the novelty or simplicity of this episode, a supreme character show for the leads (especially Jim and Pam — as they bond and then it gets awkward), along with the total ensemble, whose chemistry continues to grow. (Oh, and I have to mention the scene where Michael hides under his desk from the cameras — it’s such a fun play to the mockumentary premise, which is thus well-engaged!)

03) Episode 15: “Email Surveillance” (Aired: 11/22/05)

Michael learns that Jim’s throwing a party to which he’s not been invited.

Written by Jennifer Celotta | Directed by Paul Feig

This is a wonderful half hour for Steve Carell, as Michael gains access to his staff’s emails and finds out that he’s not been invited to a party that Jim is throwing — a terrible slight for someone who wants to be included because he wants so much to be loved. His efforts to get invited and then his eventual decision to crash the party anyway are a perfect setup to earn premise-corroborating cringe comedy that also displays his characterization — one of the series’ core attributes, around whom both its low-concept and high-concept sensibilities are situated. And, again, this is mostly a character show — with riotous moments in Michael’s improv class and then from his climactic attempt to sing a karaoke duet at Jim’s party, where Jim reluctantly indulges him (in another example of a main “relatable” lead giving a stamp of approval to this otherwise outrageous figure). Also, the Angela/Dwight secret romance is noted here — an extension of the series’ rom-com interests that, at this juncture, is a nice contrast to Jim/Pam because it’s solely comedic, pairing the ensemble’s two most authoritarian personalities.

04) Episode 16: “Christmas Party” (Aired: 12/06/05)

Michael turns a Secret Santa exchange into a Yankee Swap.

Written by Michael Schur | Directed by Charles McDougall

The Office has many strong Christmas episodes over the years, as the festivities offer a natural excuse to gather the entire ensemble of coworkers in their usual office setting, but for a more intimate or recreational purpose — with the office itself providing a juxtaposition that can help enhance cringe comedy, contrasting a professional atmosphere with the holiday’s implications of personal, familial closeness. There are several great showings in this subcategory ahead, but this may be my favorite, fleshing out some of the series’ more peripheral cast members by giving them incisive exposure in an ensemble story that inherently highlights their depictions in simple terms: through the Secret Santa gift exchange, which tells us a lot about their personalities and individual office dynamics, especially when a petty, disappointed Michael turns the affair into an uncomfortable Yankee Swap that, of course, causes conflict — particularly in the rom-com arc for Pam and Jim, as the latter had gotten a gift just for her. That’s a smart way to showcase the leading characters, the crystallizing junior ensemble, and the series’ primary romantic arc all at the same time, launching a seasonal tradition that always delivers the goods.

05) Episode 17: “Booze Cruise” (Aired: 01/05/06)

Michael forces the staff to attend an office retreat on a booze cruise.

Written by Greg Daniels | Directed by Ken Kwapis

Many of the installments with narrative movement in the main romantic arcs — especially Jim/Pam’s — tend to be popular. It’s a testament to this series’ ability to get the audience to emotionally invest in their pairing, thanks to the relatable, Everyman qualities they both share, reinforced by the mockumentary framing that not only insists on them being “real people” but also emphasizes their self-awareness relative to others in the cast, against whom they then seem even more like us, the viewers at home. “Booze Cruise” pushes Jim/Pam forward by having Jim dump his current girlfriend (played by Amy Adams) and confess his feelings for Pam to Michael, in a display of vulnerability for both men that again strengthens their bond and reiterates the evolved tone that comes with this friendlier, more empathetic perspective in the series. However, it’s great for Michael comedically as well, and what I really love about this offering — penned by showrunner Greg Daniels — is Michael’s competitiveness with the captain of the booze cruise, for he wants to be the entertainer, the one loved by both his employees and the cameras. So, it’s a terrific character show — in addition to its rom-com delights.

06) Episode 18: “The Injury” (Aired: 01/12/06)

Michael injures his foot on a grill while Dwight may have a concussion.

Written by Mindy Kaling | Directed by Bryan Gordon

My pick for this season’s Most Valuable Episode (MVE), “The Injury” mostly gets that honor because it’s the funniest, and I always want to recognize The Office for its sense of humor and the presentation of that humor, as that’s a necessary part of its situation that contributes to its greatness, always channeled through the mockumentary lens that implies a literal realism and accentuates the awkwardness of both this seemingly intimate access we’re given to these characters’ everyday “normal” lives and the magnification and/or contortion of their self-perceptions as a result of, or in spite of, an apparent awareness of the cameras. All of that is beautifully displayed in this excursion, when Michael Scott seeks sympathy after he injures his foot by burning it on a George Foreman grill next to his bed (an absurd detail that speaks to his character’s ridiculousness, but doesn’t cross the line into breaching the realism standard that’s established because we buy it for him), which then leads to him calling on a guy in a wheelchair to lecture the staff on how to treat people with disabilities. It’s exactly the kind of cringe comedy that corroborates the mockumentary premise, and it’s motivated by Michael’s childlike desire for others to care about him — to love him. But then there’s also a brilliantly intertwined subplot about Dwight injuring himself too and getting a concussion, which changes his demeanor — he essentially becomes “normal,” which is a fun turnaround predicated entirely on his usual characterization. And in the process, he bonds with Pam… before Jim eventually takes Dwight and Michael to the hospital, where Michael proves his good heart by setting aside his attention-seeking antics to care instead for someone who actually needs it (a show of affection that we never would have seen on the U.K. series, for instance). So, this is a stellar utilization of the four main leads — all of whom are thriving in The Office’s peak second season — which also demonstrates the year’s evolved sensibilities in tandem with Michael’s development, both comedically and temperamentally. Yes, there will be bolder, more outrageously hilarious entries like this ahead when the series is more comfortable being bigger and sillier on a regular basis (with more help from the wider ensemble), but not always with as much excitingly genuine support from the key characters, who uphold and focus the hijinks.

07) Episode 24: “Take Your Daughter To Work Day” (Aired: 03/16/06)

Michael tries to impress his staff’s visiting kids on Take Your Daughter To Work Day.

Written by Mindy Kaling | Directed by Victor Nelli Jr.

With a logline that spotlights the series’ workplace design — utilizing Take Your Daughter To Work Day! — this outing sits well in the low-concept part of the premise while also cleverly offering welcome insight into the characters, as we get to discover more about them through their kids and the details provided about what life is like outside the office. It’s the type of story that’s perfect for Season Two, when the situation is still fresh enough to naturally sprout notions like this, playing to the premise and developing the characters at the same time… Of course, this ultimately becomes a special sample of The Office because of how it uses Michael, who produces some crisp cringe comedy with his unvarnished display of public vulnerability, courtesy of a meta-reinforcing video where we see a young Michael blatantly say to a camera what he wants: “to get married and have 100 kids, so I can have 100 friends, and no one can say ‘no’ to being my friend.” That’s the most elemental, succinct summation of the Michael character — why he behaves the way he does, and what he’s generally going to pursue for the rest of the run, egged on by the series’ overarching rom-com sensibilities that encourage such a drive. This is a thesis-stating, situation-affirming, character-filled half hour. A favorite.

08) Episode 26: “Drug Testing” (Aired: 04/27/06)

Dwight tries to find out who is responsible for a leftover joint in the parking lot.

Written by Jennifer Celotta | Directed by Greg Daniels

Dwight Schrute is the series’ secondary comic agitator, and as this season is busy making Michael a more likable, sympathetic figure, it’s turning Dwight into a funnier one, someone who can also induce the kind of cringe comedy that proves the mockumentary aspect of the premise by serving as another un-self-aware foil to the others, yet in a different way — actively aggressing them with a hostility that Michael can’t but Dwight can, for Dwight is so ridiculous and lacks any actual power in the workplace, that he’s ultimately rendered harmless. This year not only builds out his relationships with other members in the ensemble while becoming more detail-oriented about his history and personality, it also presents the best way to utilize him in story — as the “fascist nerd” imposing law and order in the absence of Michael’s willingness to lead with authoritative force. He’s especially Barney Fife in this funny episode, as his rapport with Michael also gets fleshing out when Dwight makes a personal sacrifice for Michael — that suggests a very specific dynamic in which Dwight is also seeking Michael’s approval, just as Michael is seeking everyone else’s. Additionally, the entry’s Jim/Pam subplot is cute — one of the simplest but most original ideas for them in Season Two.

09) Episode 27: “Conflict Resolution” (Aired: 05/04/06)

Michael orders Toby to release his file of unresolved staff complaints.

Written by Greg Daniels | Directed by Charles McDougall

We’ve seen variations of this story on several other workplace sitcoms — the drudging up of old conflicts, which creates a hostile environment as individual grudges come to the fore — but The Office does it well because it has the characters who can do it justice, and this ends up being another strong showing for the ensemble, with specific relationships gaining clarity and dimension as a result of the focus. I also appreciate the incorporation of Photo Day, a fairly mundane but relatable office scenario — like Take Your Daughter To Work Day — that reflects the everyday, low-concept aspect of the premise, which is enhanced by the mockumentary format and its implication that everything is rooted in literal reality, where these people are, for the most part, just like us. That low-concept familiarity is another key part of The Office’s appeal. (Incidentally, I thought about giving this spot to “Office Olympics,” an even more crucial ensemble show, but the end of Two is simply wiser than the beginning when it comes to character, so even though it may be more important, “Conflict Resolution” is more learned.)

10) Episode 28: “Casino Night” (Aired: 05/11/06)

Michael throws a casino night while Jim plans to leave Dunder Mifflin.

Written by Steve Carell | Directed by Ken Kwapis

Two’s finale has big rom-com happenings that naturally inflate its value to fans who are invested in the characters. Specifically, the kiss at the end between Jim and Pam after he confesses his feelings for her is often regarded as a series highlight — an explosion of tension that harkens back to the great sitcom romances of NBC’s past, like Sam/Diane and Ross/Rachel. I find all that fairly by-the-numbers story-wise; storytelling-wise, however, it’s sublime, taking this opportunity to reinforce the show’s mockumentary design by framing this big moment as though we’re watching something the characters don’t know is being filmed — and that adds another layer of both excitement and situation-corroboration that speaks directly to what makes The Office special. And it’s a testament also to the freshness of the premise at this current time, where this choice is genuinely new and different — a move the series will try to repeat in the future (and explicitly so in the final season, when breaking the fourth wall is part of the main narrative) but never again with as much authentic surprise or imagination. This is peak Office. 

 

The three episodes closest to my list were: “Dwight’s Speech,” a memorable Dwight offering that boasts a big, funny centerpiece (it’s more memorable than “Drug Testing,” but the latter is a better show for his character and how he exists within the ensemble inside the series’ regular office setting), “Sexual Harassment,” a hilarious variation on last season’s nevertheless better remembered “Diversity Day” that notably introduces Todd Packer and “That’s what she said,” and “Office Olympics,” a highly formative installment that has the pointed mission of turning Michael into a more likable, nuanced character, while also positing the ensemble as capable of their own silliness outside of him — it’s a SEMINAL half hour over which I anguished not highlighting above. Meanwhile, I like the rest of the season a lot, but some other entries I really enjoy and would love to make mention of now include: “The Fire,” a solid early showcase for the ensemble that has a lot of nice Ryan moments especially, “Performance Review,” which has fun with the office dynamics after Michael’s hookup with Jan, “The Secret,” a great Michael showing that follows Jim’s reveal of his feelings for Pam, “Valentine’s Day,” where The Office is all in on its NBC-approved rom-com overtones, and “Michael’s Birthday,” which is yet another example of how Two has successfully reformulated its central character, who shines in a story all about him. Again, I like everything here — it’s that good.

 

*** The MVE Award for the Best Episode from Season Two of The Office goes to…

“The Injury”

 

 

Come back next week for Season Three! And stay tuned tomorrow for a new Wildcard!

12 thoughts on “The Ten Best THE OFFICE Episodes of Season Two

  1. “The Dundies” and “The Injury” are my favorites from this season. Season 2 is tied for me with Season 5 as my favorite. I was never a huge Jim/Pam shipper but I appreciated their chemistry and how the story was plotted early on. You could definitely see the Ross/Rachel influences.

  2. I genuinely had no clue what your MVE would be since there are so many strong episodes this season. I do think you picked a good one!

    • Hi, Charlie! Thanks for reading and commenting.

      Yes, it’s a great showing for the series’ four primary characters, evidencing the show’s evolving tone.

  3. Ive always thought that “Office Olympics” was overrated. I know that some of the writers have said the end with Michael crying was a huge turning point for his character but the episode is meh to me. So Im glad you left it off at the bottom.

    • Hi, Brandon! Thanks for reading and commenting.

      I like “Office Olympics” but I agree with you that its role in softening Michael is a touch overstated — I think “The Dundies” does most of the heavy-lifting in Season Two for launching this new, more likable portrayal.

  4. The Christmas episode from this season is my favorite Christmas episode of the series, with the whole idea of a Secret Santa becoming a Yankee Swap. Hilarious.

  5. You mention here that you like all 22 episodes from Season Two. What other sitcoms and their seasons come to mind where you can say that you like every single episode?

    • Hi, Paul! Thanks for reading and commenting.

      That’s an interesting question that requires some thought. I think I’ll flag it for possible use in a future Q&A entry!

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