Continuing on from last week’s TV Thursday, focusing on the first season of The Office, I decided to pull out five highlight episodes from Season Two, when the show found its feet and really started finding its voice. So here are five of my favorite episodes from Season Two, in chronological order.
1. The Dundies
The Office returned for its second season right out of the gate with an all-time great episode. The Dundies centers around Michael Scott’s annual branch award show, held at the local Chili’s. The season premiere cleverly uses the “senior superlative”-style Dundies to efficiently re-introduce the characters, even fleshing out the supporting characters who we barely met in the first season, with quick throwaway gags both of the present year’s show and the Dundies of the past, recorded on fuzzy VHS. Dwight is reinforced as Michael’s lap dog in a subplot, taking him into the women’s restroom to track down a bit of graffitti about Michael. And everything between Jim and Pam is a pitch perfect reintroduction to their will they-won’t they romance, with Jim tricking Michael into switching up his traditional “Longest Engagement” award for Pam and Pam getting a little too drunk, kissing Jim in celebration, and giving him a look that says so much, while saying nothing at all.
2. Office Olympics
Much like The Dundies, the Office Olympics episodes does an incredible job putting a focus on the supporting cast of characters. With Michael and Dwight away signing on Michael’s new condo, Jim and Pam take the lead back at the office and bring everyone together for a collection of random competitions like who can eat the most M&M’s and “Flonkerton” - which in English translates to “Box of Paper Snowshoe Racing.” There are a lot of great little moments here that highlight how well the ensemble worked together and the fun they could have with something as mundane as an office of a mid-range paper company.
3. Booze Cruise
I think a general rule of thumb for The Office is that almost every time the Dunder Mifflin team actually leaves the office itself, we’re for a treat. Getting to see the crew in a more “natural” environment (as natural as a booze cruise can be), is always a nice change of pace (see also the above Dundies episode). This episode is absolutely a Michael Scott showcase episode, with Michael constantly trying to work in his nautically-based motivational metaphors and constantly being shot down by the ship’s Captain Jack (a guest star turn from Rob Riggle). He ultimately lands the biggest moment of this though when Jim confides in Michael his feelings for Pam and Michael tells him to “never, ever, ever give up.” The episode also gets bonus points for one of my absolute favorite cold opens/Jim pranks, with Jim putting all of Dwight’s stuff in the vending machine.
4. The Injury
Another incredible episode for Michael, as we get to see him at his neediest. After burning his foot on his George Foreman grill, he begs the office to look after his every beck and call. Meanwhile, Dwight suffers an actual accident and a concussion in his rush to take care of Michael so we get to see a softer side of the Dwight/Jim/Pam dynamic as Jim and Pam look after the concussed Dwight (who, thanks to his trauma, is being a lot nicer to both and cracking jokes with them).
5. Casino Night
This one’s a cheat, given its two-part finale nature but Michael’s idea to turn the warehouse into a casino-based fundraiser adds a bit of class to the proceedings. Michael’s main plot centers around his belief that he’s accidentally set himself up with two dates joining him but the stereotypical hijinx only occur in his mind. Meanwhile, the star of the show is the culmination of the series long run between Jim and Pam, with Jim confessing his feelings to Pam and the two sharing an intimate moment to close out the show, leaving the audience to wonder what they would return to in season three.