The List: Top 10 ‘The Office’ Episodes

The Office ended 10 years ago this week. I was an early champion of the show, but fell off in its third season when the show sent Jim to Stamford, then back to Scranton with his new girlfriend Karen (Rashida Jones) and ultra-annoying Andy (Ed Helms). But the show kept extending its life thanks to riding a wave of new-ish technology. After its short, low-rated first season, iTunes downloads convinced NBC to give it another shot. Then, DVD sales kept it a staple of the network’s attempts to resurrect Must See TV. And its long run on Netflix made it one of the most popular shows in the world. The latter two developments meant it was always on in someone’s dorm room or apartment in my college years and after.

So to celebrate the legacy of one of the most beloved shows of the 21st Century, here are my 10 favorite episodes. (But do take this list with a grain of salt; I like “Scott’s Tots.”)

10. “Traveling Salesmen” (Season 3, Episode 13)
In this underrated episode, the crew at Dunder Mifflin pairs up to make some sales calls, leading to great visual gags like Phyllis and Karen with matching blowouts and Ryan freezing in front of Stanley’s all-Black clientele. This is one of the rare episodes that shows some employees are actually quite good at their jobs! But the main reason I chose this over many other fine selections was Dwight’s principled stand in his relationship with Angela. Though they wouldn’t get married until the series finale, his willingness to protect her job and her reputation make for a romantic moment that’s not maudlin.

9. “Gay Witch Hunt” (Season 3, Episode 1)
Creator Greg Daniels won the show’s only writing Emmy for this cringe-inducing half-hour, which sees Michael out Oscar, then compound the awkwardness by kissing him on the lips. Every conference room scene is wildly uncomfortable but undeniably hilarious. It also serves as an introduction to the doomed Stamford branch, which isn’t nearly as laid-back as Scranton.

8. “Health Care” (Season 1, Episode 3)
Season 1 gets a bad rap, but while it’s a little rough around the edges, I’ve always liked Michael a little meaner and a lot sweatier. (So more like David Brent.) Rather than admit corporate is demanding cuts to the company health insurance plans, he passes the buck to Dwight, who lets the busywork go to his head. The fake diseases the other employees make kill me, but Michael trying and failing to come up with a “surprise” to make up for the overlords’ rotten penny-pinching hits close to home.

7. “Women’s Appreciation” (Season 3, Episode 22)
If you thought Michael and Oscar were awkward, the entire opening had me covering my eyes. After Phyllis is attacked by a flasher in the parking lot, Michael mocks her, then pretends his thumb is his penis. It’s insensitive but also incredibly funny. But the episode packs an emotional punch as Michael takes all his female employees out for lunch and shopping, and shares his relationship difficulties with them, getting brutally honest feedback in return.

6. “Christmas Party” (Season 2, Episode 10)
By Season 2, Michael had become less of a dick and more of a needy people-pleaser. This disastrous holiday gathering represents him at his worst/best. After spending more than 10 times the agreed-upon limit on his Secret Santa gift for Ryan, he’s annoyed his gift from Phyllis is homemade. This obnoxiousness is Michael in a nutshell: I did something I shouldn’t have (with good intentions) and people are mad, but I’m the boss and I need everyone to love me so I have to fix this. His solution? A white elephant exchange, which sees everyone fighting over the iPod and Jim unable to get every piece of his romantic multi-gift surprise for Pam. It’s no wonder everyone wants to get drunk after this ordeal.

5. “The Injury” (Season 2, Episode 12)
Michael’s dumbest moment provides some of the show’s biggest laughs. After burning his foot on his George Foreman Grill, he milks the injury for all its worth, comparing his plight to the permanent wheelchair use of the office manager and a concussed Dwight. Written by co-star (and future TV megastar) Mindy Kaling, the show features one of the best jokes in the entire series:

Michael presents his bubble-wrapped foot to the unamused Stanley, asking “What does it look like?” To which Stanley deadpans, “Mail Boxes Etc.”

4. “Stress Relief” (Season 5, Episodes 14-15)
The episode that got me back into the show after dropping out due to its focus on Jim and Pam. While I don’t love it quite as much as the first time I saw it directly after Super Bowl XLIII, the cold open remains the single funniest thing the show has ever done. Matching those highs were basically impossible, though the CPR training comes close. And while the fake movie Andy watches with Jim and Pam is pretty stupid, the emotions it unearths still feel earned.

3. “Goodbye, Michael” (Season 7, Episode 22)
Goodbyes are tough, and whatever Michael’s strengths as a boss and a person, he often bailed at the first sign of discomfort or distress. Hence treating his penultimate day at the company as his final day without telling anyone. It’s sneaky but understandable, and the perfect send-off for Michael and Carell. While the show continued for two more so-so seasons, the impact of this episode hasn’t diminished because we didn’t see Michael again until the finale in a perfectly executed cameo. So did Carell get a long overdue Emmy for his best work on the show? No! Voters picked Jim fucking Parsons, whose “Bazinga”-filled reign of terror in this category wouldn’t end until 2015.

2. “Dinner Party” (Season 4, Episode 13)
As a sicko, I love episodes that end with everyone unhappy. So of course I nearly put this wholly uncomfortable half-hour – in which Michael and Jan’s triple-date goes horribly awry – at the top. Like a much pettier and goofier Who’s Afraid of Virginia Woolf?, there’s some raw emotion underneath the jokes, accusations and outbursts.

1. “Niagara” (Season 6, Episodes 4-5)
This two-parter has all the show’s strengths on display: impeccably crafted jokes of every type, well-meaning but terribly executed efforts from Michael, and genuine heart. Jim cutting his tie is a small gesture, but one of the most romantic things I’ve ever seen on television. This episode deploys sentimentality when needed, but doesn’t rely on it, as so many wedding episodes tend to do. The ceremony may have not been perfect, but this episode was.

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