Season Four of The Office suffered an abbreviated 14-episode season as a result of the 2007-2008 Writers’ Strike. While NBC was able to maneuver a lot of these into hour-long episodes, I’ve decided to cut down the usual “Five Favorite Episodes” feature to “Three Favorite Episodes.”
This episode devotes a lot of time to the Michael/Jan relationship and how truly destructive it is on Michael’s finances as we learn that Jan is basically freeloading off of him. Michael has picked up a second job working on phone sales and it’s affecting his work at Dundler Mifflin. Meanwhile, Jim and Pam decide to stay at Dwight’s bed and breakfast. There’s the classic moment of Michael yelling out “I declare bankruptcy!” as if that would work. But the real kicker is a touching stairwell scene where Jim confides to a depressed Dwight (mourning the end of his relationship with Angela) that he left Scranton because not being with Pam was unbearable and he wouldn’t wish that on his worst enemy. It’s a beautifully-played heartfelt moment followed up with Jim immediately going to Pam and passionately kissing her in the office.
2. Dinner Party
Arguably, one of the best, cringiest episodes of the entire series, Dinner Party has Michael tricking Jim and Pam into finally joining him and Jan for dinner at his place. The tour of the Jan-ified condo is hilarious as we see that Michael sleeps on a small bench at the end of the bed and his two most prized possessions are his tiny tiny tiny wall-mounted plasma screen tv and his neon beer sign of a busty barmaid. Their relationship explodes in a fireball of awkward tension scored to the soundtrack of Jan’s former assistant Hunter singing “That One Night:” presumably an ode to a passionate evening of love between him and Jan. It’s beautiful and hilarious.
3. Goodbye, Toby
Michael’s dreams are coming true as Toby has announced he’s leaving Dunder Mifflin and moving to Costa Rica. Michael can’t contain his excitement and decides to chip in extra funds for an extravagant going away party for him, including a Ferris wheel in the parking lot. When Jim starts to see the beefed-up party, he throws in some of his own cash to get fireworks and plan for an end-of-season proposal. Andy steals his thunder, however, and takes the opportunity to propose to Angela instead. Meanwhile, we also get the introduction of Michael Scott’s soulmate Holly Flax here as the HR rep replacing the departing Toby. Great humor and heart to wrap up the season.