Honorable Mention: “The Convict,” (Season 3, Episode 9)
Much to Michael’s surprise he learns that Martin, one of the former Stamford employees, is a former criminal. The staff learns that his time was spent in a white-collar prison, and begins to wonder if Martin’s prison is better than Dunder Mifflin. Michael then gives a presentation on the miseries of prison, with most of his ideas fueled from television prisons. Upset that he is not being taken seriously, he then locks his employees in the conference room. At the end of the day, Martin decides to quit rather than continue working with Michael.
10. “Casino Night,” (Season 2, Episode 22)
In this season finale, Michael organizes a casino night for charity, but accidentally invites two dates, his boss Jan, and his realtor Carol. He ends up beginning a relationship with Carol. Jan reacts calmly, but later she leaves early with an overnight bag, revealing that she had intended to stay with Michael. In the most anticipated announcement in the show’s history, Jim reveals to Pam that he is in love with her, and they share a kiss.
9. “Diversity Day,” (Season 1, Episode 2)
Michael provides a cringe-worthy imitation of a Chris Rock routine and forces the staff to undergo a racial diversity seminar. A consultant arrives to teach the staff about tolerance and diversity, but Michael insists on sharing his own knowledge and develops his own seminar. His idea at group involvement is to assign each staff member an index card with a different race on it, in which they must ask “yes or no” questions to determine their race which is unbelievably awkward for them and us. The episode ends with Pam falling asleep on Jim’s shoulder at the end of the meeting; he concludes that it was “not a bad day.”
8. “Fun Run,” (Season 4, Episode 1)
After Michael hits Meredith with his car in the parking lot of Dunder Mifflin Scranton, she learns she is infected with rabies. Angela asks Dwight to care for her sick cat, but Dwight mercy-kills the animal, leading to relationship problems and their eventual breakup. After being videoed in public by the camera crew, Pam announces that she and Jim are now dating, but they do not share this with their co-workers. Feeling guilty about the incident with Meredith, Michael decides to host “Michael Scott’s Dunder Mifflin Scranton Meredith Palmer Memorial Celebrity Rabies Awareness Pro-Am Fun Run Race For The Cure”, although his employees are less than enthused. Toby wins the race, and a depressed and dehydrated Michael is finally forgiven by Meredith.
7. “Christmas Party,” (Season 2, Episode 10)
At this year’s company party, Michael tries to turn the original grab bag into a game where they can now steal each other’s gifts. Michael went way above his price limit, and brought an iPod for his original person in the grab bag, Ryan. On the other hand Phyllis stuck to the price range and made a homemade oven mitt. Everyone in the office tries to steal the iPod, but Jim is more worried about the teapot. Jim had Pam this year, and made a very sentimental gift of all their favorite things along with a card revealing his true feelings which also keeps getting stolen in the grab bag. Seeing how bad his Christmas idea has ruined the party, Michael buys alcohol for everyone. Additionally, in the end Pam did get the teapot, but Jim chose to keep the card.
6. “Money,” (Season 4, Episodes 7&8)
We discover that Michael is working a second job as a telemarketer and must also declare bankruptcy. Ryan and Jan force him to quit his job, and Jan reassures him they will find other ways to make ends meet. Pam and Jim take their first overnight trip to Dwight’s beet farm, Schrute Farms. After hearing Dwight cry in the middle of the night because of his recent break-up with Angela, Jim comforts Dwight at work the next day, explaining that he wouldn’t wish the pain he felt when he wasn’t with Pam on his worst enemy. In a weird moment, they understand each other which makes it uncomfortable for both of them. Dwight returns to his normal self, and everything is right again.
5. “The Secret,” (Season 2, Episode 13)
Jim confesses his crush on Pam to Michael, and Jim becomes desperate to make sure Michael keeps the secret. Although Michael says he won’t “for as long as I possibly can.” Michael ends up revealing the secret anyway. Jim tells Pam that he had a crush on her years ago, but that it ended when he found out she was engaged. Meanwhile, Oscar calls in sick, prompting Dwight to spy on him to determine whether he was telling the truth. Oscar is revealed to be gay to us, but Dwight does not realize it.
4. “Finale,” (Season 9, Episodes 24 & 25)
One year after the airing of the documentary, the viewer’s learn the aftermath of the airing. The “cast” of present and past employees of Dunder Mifflin come together for the wedding of Dwight and Angela at the Schrute farms. We get to enjoy nostalgia as Jim plays his “best prank ever” on Dwight. Jim was originally asked by Dwight to be his best man, but with Jim’s doing, Michael Scott shows up and takes his place providing one of the best quotes ever, “I can’t believe you came! / That’s what she said”. The series ends the best way possible, with the group sitting in the office reminiscing and providing their final interviews.
3. “Office Olympics,” (Season 2, Episode 3)
When Michael and Dwight leave to close a deal on Michael’s new condominium, the rest of the office is bored out of their minds. Michael gets really stressed and depressed when he realizes how long he will be paying for his condo. In the meantime, Pam and Jim decide to invent the Office Olympics to cure their boredom. They create multiple games and all compete in these games using office supplies. Pam makes medals out of yogurt lids, and we get to see each character truly illuminated. Michael and Dwight return, the event stops abruptly and everyone returns to their desks. Jim is still playing and gives the gold medal to Michael, for closing the purchase of his condominium and Michael gets teary eyed. This is symbolic as he has made this huge purchase, and also his love for his co-workers.
2. “The Dundies,” (Season 2, episode 1)
The start of the second season, introduced The Dundies, Dunder Mifflin’s own awards ceremony held annually at the Scranton Chili’s. The very best (or worst) of Michael Scott was on public display, from his embarrassing and uncomfortable imitations and lame jokes of his too obvious man crush on Ryan. The crowd seems unresponsive, but luckily drunken Pam saves the day. Her excitement livens up the crowd, and eventually gets them kicked out. We immediately get teased when Pam drunkenly kissed Jim while she is leaving after her over excitement of winning the “Whitest Sneakers Award”.
1. “Goodbye Michael,” (Season 7, episode 22)
Michael prepares to leave for Colorado with Holly, and is looking forward to not being the usual center of attention and told everyone he was leaving the day after he actually was. Jim learned the truth, and then Michael in turn spends his last day in the office saying goodbye to everyone individually, wanting no drama to ensue. At the airport, Michael got in a good final ‘That’s what she said’ joke, and then the documentary microphone was off. Pam and Michael have a final goodbye that viewers saw but couldn’t hear. With that, the show lost the World’s Best Boss.