The Office: 5 Funniest (& 5 Saddest) Episodes Of Season 2

The first season of the American version of The Office landed with an average response, with most of the criticism landed on copying too much from the British counterpart. But on its next season, the show is able to carve its own identity and break ground for the cast ensemble.

Likewise, Season 2 consistently gave several of the funniest episodes and character highlights of the sitcom. And yet, it also delivered some of the show’s saddest moments. This season not only solidified the trajectory for The Office’s quality, but also cemented the emotional weight to everyone’s favorite Dunder Mifflin staff.

10 Funniest: “Email Surveillance”

The fifteenth episode of the season, “Email Surveillance” finds Michael Scott (Steve Carell) in an opportune position when he gets to read his employees’ emails. So, it devastates him when he finds out that Jim Halpert (John Krasinski) is throwing a house party that night, and he is not invited.

Michael compensates that by attending an improv class, which contains the funniest highlights, including his spy alter ego Michael Scarn. Several funniest bits include Michael and Jim singing a duet, and Dwight and Angela being caught on camera making out.

9 Saddest: “Dwight’s Speech”

While not truly sad, the episode “Dwight’s Speech” contains a moving moment for both Michael and Dwight (Rainn Wilson). In it, the latter got cold feet when he is invited to deliver a speech as Salesman of the Year. When Michael’s attempt to save face failed, Dwight got inspired and delivered a fascist-like speech. All the while, Michael did not watch, speechless of Dwight’s delivery.

But the episode’s heaviest arcs are back at Scranton when Kelly (Mindy Kaling) is reactive to Ryan’s commitment fears, and Jim dreads about Pam’s wedding.

8 Funniest: “Christmas Party”

The first Christmas-themed episode for The Office, “Christmas Party” started out simple with the Dunder Mifflin staff holding a Secret Santa with gifts amounting to $20. However, that backfires when Michael intends to give Ryan (B.J. Novak) with an iPod worth $400 but initiates a fierce game of Yankee Swap.

Seeing the employees try hard (or not) on their presents is really funny. But the Yankee Swap sequence and the resulting booze for the party are what makes the episode truly hysterical. Though, Meredith should have stayed sober for long.

7 Saddest: “Conflict Resolution”

As indicated by the title, situations escalate within the Scranton branch. The titular “Conflict Resolution” comes from Michael Scott’s attempts to resolve every employee’s conflict after acquiring Toby’s list of complaints. But it only ends up throwing gasoline to the fire, especially when Dwight threatens to quit and Jim hints of his move to Stamford.

The serious tone ups the emotional stakes for the Scranton saga. And it is really tense to see it end on a sad note. The sour photo opportunity does not help matters for the staff.

6 Funniest: “Booze Cruise”

But on the lighter side, there is the classic “Booze Cruise”. This episode finds Michael and his staff on a motivational cruise, where he uses the setup as both a party and a leadership training. But Captain Jack (Rob Riggle) keeps interfering with his plans.

The episode is chock-full of hilarious moments, from Dwight being fooled to use a prop ship wheel to Michael’s Titanic moment, down to the group thinking the ship is sinking. However, the most notable moment goes to Michael motivating a heartbroken Jim to pursue Pam.

5 Saddest: “Office Olympics”

“Office Olympics” offers that balance of heavy characters decision and heart-warming results. This episode sees Michael and Dwight inspecting the former’s new condominium. As Dwight sees problems inside the unit, Michael begins having cold feet since its purchase entails a huge amount of money. All the while, Jim and Pam organize an Olympics-themed office games.

The saddest part of this chapter is Michael’s difficult decision of his condo’s purchase plan. Not known for being responsible, he realizes how much of a toll this would take. So, the staff awards him.

4 Funniest: “The Injury”

“The Injury” gives an opportunity for Rainn Wilson to show his comedic range. The episode involves Michael accidentally burning his foot on his George Foreman grill and Dwight coming to assist him. However, on the way, he crashes his car and is left concussed. The concussion transformed Dwight to be a nicer version of himself.

This saga relies on the overlooked Michael trying to stray attention away from an off-kilter Dwight to hilarious degrees. Dwight stealing Michael’s signature catchphrase is a thing of beauty, summing up a nicer, weirder Dwight.

3 Saddest: “Halloween”

This episode continues the ongoing storyline of the downsizing of several Dunder Mifflin employees. As Michael projects, he does whatever it takes to keep his company tight. But on “Halloween”, he is placed on a precarious situation where he has to drop either Creed Bratton or Devon White. Creed becomes persuasive and smooth-talking to Michael not to let him go.

Michael is the most devastated in this chapter, even if he sported a conjoined twin paper mache costume. He was upset over firing Devon and poured his grievances to Jim. In the end, he heartwarmingly gives candy to excited trick-or-treaters.

2 Funniest: “The Dundies”

“The Dundies” are a golden opportunity for Michael to hand out dubious awards to his staff, much to their chagrin. But they are forced to watch Michael crash and burn as MC on a spectacular awards show at Chili’s. And the genuine reactions by the characters are just delightfully funny.

However, the MVP award goes to Pam (Jenna Fischer), whose drunken stupor causes her to disturb customers, take their drinks and make a laugh-out-loud speech in the Dundies. Though, her drunken enthusiasm led her to being banned from Chili’s, but gained a sweet moment between her and Jim. Such sweetness.

1 Saddest: “Casino Night”

Speaking of the Jim-Pam storyline, it reached a milestone on “Casino Night” when the chips are laid for the future of their relationship. And it is just one of the dramatic moments that filled up the episode. The story basically revolves on the Scranton branch holding a casino charity event.

Each party has a role to play. Even Michael got to invite his boss Jan Levinson (Melora Hardin) and his real-estate agent Carol Stills (Nancy Carell); though, their encounter led to a heart-breaking moment. But the most heart-breaking goes to Jim ultimately confessing his love for Pam and kissing her. It is a tender moment.

About The Author