After a couple weeks away, I wanted to return to this ongoing series highlighting some of my favorite episodes of every season of The Office. So here are five of the best from Season Five.
1. Weight Loss
Over the course of the show, we didn’t often see what the good people of Dunder Mifflin were up to during the summer months while the show was off the air. Weight loss cleverly gives us a series of weekly check-ins based around the office’s weekly weigh-in in a corporate-wide attempt to lose weight. It also of course shows us Pam going off to New York for art school and hints at how much Jim and Pam miss each other in those initial weeks. The highlight for me, no surprise, is the impromptu gas-station proposal in the rain as the pair meet-up between Scranton and New York.
2. Business Trip
Dealing with the aftermath of Michael and Holly’s all-to-brief romance, Business Trip stands out to me because it showed Michael standing up for something he really cared about and getting appropriately pissed off at David Wallace for taking away the best thing that ever happened to him. There’s also the heartbreak of Pam suddenly failing one of her classes and ultimately returning home to be with Jim rather than continue pursuing her passion. Probably one of the saddest episodes in the history of the show but the vulnerability of the characters here always hits me hard.
3. New Boss
Idris Elba continues the stellar luck The Office had plugging in actors from The Wire as a new VP over Michael who also gets a bad first impression of Jim that he never really shakes. His no-nonsense accounting background immediately puts a stop to wasteful expenses like *gasp* Michael’s fifteenth anniversary party and Michael becomes so fed up that he actually quits the company. It sets up a series of jarring new dynamics and helped provide the shot in the arm the season needed to close out the back half of the season.
4. Michael Scott Paper Company
This episode is really standing in for the whole Michael Scott Paper Company arc that saw the odd pairing of Pam and Ryan join Michael in his crazy attempt to start his own company. This particular episode has them moving into a cramped space back at the business park next to the Dundler Mifflin offices. Pam realizes what a mistake she’s made and unsuccessfully tries to get her old job back. But she wins the day in the end, landing the Michael Scott Paper Company’s first sale. The funnest detail of this episode though might be how they redesigned the show’s opening credits to be centered around the Michael Scott Paper Company instead of Dunder Mifflin.
5. Company Picnic
Another season, another finale making my list. The show was good at sending the audience off into the summer break happy. Company Picnic of course has the great silent moment of Jim and Pam discovering they’re gonna be parents but this episode really stands out for me because of the Michael/Holly reunion. They immediately click back in sync and it’s almost cruel how much the show kept them apart. Even here, Holly is still with her boyfriend A.J., whom Michael met earlier in the season on his lecture circuit. But the two deliver their perfect chemistry performing a Slumdog Millionaire parody and accidentally announcing a branch closure to the whole company. Michael foreshadows the rest of their relationships saying (much like Jim and Pam before them) that his relationship with Holly will take a long time, but it will be perfect and he’s in no rush.