Season 4, episodes 7 & 8
Aired: Oct. 18, 2007
The main plot — where it’s discovered that Michael Scott (Steve Carell) is working a second job and must also declare bankruptcy — is fairly forgettable. But the B storyline, in which Pam (Jenna Fischer) and Jim (John Krasinski) take their first overnight trip to — where else? — the beet farm owned by Dwight (Rainn Wilson), is a sweet relationship changer. After hearing Dwight cry in the middle of the night because of his recent break-up with Angela (Angela Kinsey), 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. Dwight and Jim will never be best friends, but this is the point in the show where they begin to form a grudging respect?and a weird understanding.
Best Line: ”I’m very passionate about Italian food?. In fact, I’m in love with Italian food.” —Jim Halpert
Season 9, episodes 24 & 25
Aired: May 16, 2013
The series’ final episode with the Dunder Mifflin gang was bound to bring on the tears — viewers probably just didn’t expect them to come so early or often (that’s what she…oh, you get it). Fans got to see the aftermath of the documentary airing, including a moving Q&A, as well as witness Dwight and Angela finally getting hitched at Schrute farm. Equal parts funny and moving, the supersized, 75-minute installment was the perfect way to say goodbye to America’s favorite paper crew. Plus, viewers got to witness Jim’s ”best prank ever.” Not a bad way to go out.
Best Line: ”I can’t believe you came!” / ”That’s what she said.” —Dwight Schrute and Michael Scott
13. ''Goodbye Michael''
Season 7, episode 22
Aired: April 28, 2011
Comedies don’t normally make you cry, but Michael’s departure for a new life in Colorado with Holly (Amy Ryan) was the exception that proved the rule. The man who always demanded to be the center of attention didn’t want tearful goodbyes, so he told everyone he was leaving a day after he actually was. Jim figured out what was going on, and the two shared a few tearful last words about Michael being the best boss Jim ever had. 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.
Best Line: ”The people that you work with, are just, when you get down to it, your very best friends. They say on your deathbed you never wish you spent more time at the office. But I will. Gotta be a lot better than a deathbed. ” —Michael Scott
12. ''The Secret''
Season 2, episode 13
Aired: Jan. 19, 2006
This episode pulled off one heck of a great reveal. After Jim confessed his crush on Pam to Michael, Jim became desperate to make sure Michael kept the secret to himself. (Michael himself noncommittally said he planned to stay mum ”for as long as I possibly can.”) All the while, another secret threatened to emerge: Oscar (Oscar Nuñez) was gay. The fact that the show was able to clue viewers in — while keeping volunteer sheriff’s deputy Dwight in the dark — was an inspired twist.
Best Line: ”There are several different ways to tell if a perp is lying. The liar will avoid direct eye contact. The liar will cover part of his or her face with his hands, especially the mouth. The liar will perspire. Unfortunately, I spoke to Oscar on the phone so none of this is useful.” —Dwight Schrute
11. ''Goodbye Toby''
Season 4, episodes 18 & 19
Aired: May 15, 2008
This episode had everything: A confrontation between Michael and an on-his-way-to-Costa-Rica Toby (Paul Lieberstein), the first appearance by Holly Flax (the HR rep who would become Michael’s great love), an almost-proposal from Jim to Pam, and a real proposal from Andy to Angela. Not to mention one of the best episode tags ever: Phyllis (Phyllis Smith) busting Dwight and Angela as they secretly hooked up at the office.
Best Line: ”Toby has been cruisin’ for a bruisin’ for 12 years. And I am now his cruise director. And my name is Captain Bruisin.” —Michael Scott
10 .''Christmas Party''
Season 2, episode 10
Aired: Dec. 6, 2005
The Office always did Christmas well (Benihana celebration, anyone?), but the game of Yankee Swap in season 2 was a series high. Michael Scott’s rejection of Phyllis’s homemade oven mitt shows his character at its most boorish, but Jim’s super-detailed teapot gift for Pam provided fans another small tease of how wonderful it would be when the two finally got together. Happy birthday, Jesus: Your party ended with everyone drunk on vodka and Meredith (Kate Flannery) flashing Michael — who naturally took a picture.
Best Line: ”I do the nicest thing that anyone’s ever done for these people, and they freak-out. Well happy birthday, Jesus. Sorry your party’s so lame.” —Michael Scott
9. ''Stress Relief (Part 2)''
Season 5, episode 15
Aired: Feb. 1, 2009
After deciding the Dunder Mifflin crew had become stressed out, Michael organized a comic roast of himself in the warehouse. Naturally, Michael’s ego wouldn’t allow him to handle the gang’s insults, so he stormed off and proceeded to take a personal day. Everyone became concerned they went too far, but you can’t keep Michael Scott down for long. He shows up at work to roast everyone with killer one-liners (see below).
Best Line: ”Jim, you’re 6’11”, and you weigh 90 pounds, Gumby has a better body than you. Boom, roasted. Dwight, you’re a kiss-ass. Boom, roasted. Pam, you failed art school. Boom, roasted. Meredith, you’ve slept with so many guys you’re starting to look like one. Boom, roasted. Kevin, I can’t decide between a fat joke or a dumb joke. Boom, roasted. Creed, your teeth called, and your breath stinks. Boom, roasted. Angela, where’s Angela? Whoa, there you are. I didn’t see you behind that grain of rice! Boom, roasted! Stanley! You crush your wife during sex, and your heart sucks. Boom, roasted. [Stanley starts laughing] Oscar you are [distracted by Stanley] Oscar, you’re gay! Andy, Cornell called, they think you suck! And you’re gayer than Oscar. Boom, roasted! ” —Michael Scott
8. ''Dinner Party''
Season 4, episode 13
Aired: April 10, 2008
What could be better than a mandatory dinner party at your boss’s house? Anything. This episode was one of the high points of the entire show for cringe comedy — from the likely affair between Michael’s boss-turned-live-in girlfriend Jan (Melora Hardin) and her assistant Hunter (Nicholas D’Agosto) to Jan’s obsession with Pam and Michael’s ”relationship.” We can’t forget the candle business or the vasectomy talk — and that’s all before Dwight showed up with his babysitter/girlfriend (Beth Grant). Viewers may have wanted the party to last for hours, but Jim and Pam couldn’t get out of there fast enough.
Best Line: ”Michael and Jan seem to be playing their own separate game, and it’s called, ”Let’s See How Uncomfortable We Can Make Our Guests.” And they’re both winning.” —Jim Halpert
7. ''Beach Games''
Season 3, episode 23
Aired: May 10, 2007
When Michael becomes convinced he’s destined for a new job at corporate, he takes his entire staff (save for Toby) to the beach to find his replacement through a series of challenges including sumo wrestling and a hot dog eating contest. While it was fun to watch Angela get her Lady MacBeth on, the real treat was watching Pam (who’d just walked across hot coals) talk to Jim about their strained friendship, which laid the groundwork for a number of end-of-season gamechangers.
Best Line: ”Jim Halpert. Pros: Smart, cool, good-looking. Remind you of anybody you know? Cons: Not a hard worker. I can spend all day on a project, and he will finish the same project in half an hour. So that should tell you something.” —Michael Scott, weighing his options for the next branch manager
6. ''The Alliance''
Season 1, episode 4
Aired: April 12, 2005
This episode expanded and explored two relationships that would remain constant over nine seasons: Dwight and Jim’s prank-filled rivalry, as well as Jim and Pam as an unstoppable team. The fact that this episode ends with Dwight willingly hiding in a taped box in the warehouse? Perfection.
Best Line: ”Studies have shown that more information gets passed through watercooler gossip than through official memos — which puts me at a disadvantage because…I bring my own water to work.” —Dwight Schrute
5. ''The Injury''
Season 2, episode 12
Aired: Jan. 12, 2006
Some episodes didn’t have a ton of plot — they were just side-splittingly hilarious. Michael burning his foot on a George Foreman grill is the latter. It was a great showcase for Steve Carell as Michael revealed his constant need for attention. We dare you not to chuckle at his description of the incident.
Best Line: ”I enjoy having breakfast in bed. I like waking up to the smell of bacon — sue me. And since I don’t have a butler, I have to do it myself. So most nights before I go to bed I will lay six strips of bacon out on my George Foreman Grill. Then I go to sleep. When I wake up, I plug in the grill. I go back to sleep again. Then I wake up to the smell of crackling bacon. It is delicious. It’s good for me. It’s the perfect way to start the day. Today I got up, I stepped onto the grill and it clamped down on my foot. That’s it. I don’t see what’s so hard to believe about that. ” —Michael Scott
4. ''The Convict''
Season 3, episode 9
Aired: Nov. 30, 2006
Long-term fans of The Office know that some of the group’s best comedic work comes from when the whole gang gathers in the conference room for one of Michael’s meetings. When Michael channeled Prison Mike to tell the Dunder Mifflin crew that prison was a lot scarier than they might think, ”The Convict” was top-to-bottom hilarious from writing to reaction shots. This episode is also responsible for a great gag that had Dwight bending over with a wad of cash coming out of his pocket to ”tempt” a new worker who did some time in lockdown.
Best Line: ”The worst thing about prison was the…was the dementors. They were flying all over the place and they were scary and then they’d come down and they’d suck the soul out of your body. And it hurt! ” —Michael Scott, as Prison Mike
3. ''Diversity Day''
Season 1, episode 2
Aired: March 29, 2005
The second episode of the show set the tone for many an uncomfortable holiday to come. Michael Scott performed a controversial Chris Rock routine, resulting in a mandatory diversity seminar. But Scott — as will quickly become the custom on the show — decides to upstage the corporate lesson and run his own well-meaning but deeply flawed ”Diversity Tomorrow” program. The show’s cringing-while-laughing set-up would be too much for some viewers, but many others who watched cast members guessing ethnicities written on index cards taped to their foreheads was a welcome change to the hackneyed humor of the contemporary sitcom landscape.
Best Line: ”Abraham Lincoln once said, ‘If you are a racist, I will attack you with the North.”’ —Michael Scott
2. ''Casino Night''
Season 2, episode 22
Aired: May 11, 2006
When the Dunder Mifflin gang had a special event, you knew there was going to be trouble — and big laughs. Michael Scott’s season-ending fundraiser (not to be confused with a Fun raiser!) provided many classic moments, from the first date of Michael and his realtor Carol (played by Carell’s real-life wife Nancy Walls) to Carol meeting Jan. Each character had a moment to shine, and the whole thing culminated in one hell of a romantic cliffhanger: After Jim confessed his feelings for Pam and she turned him down, he came up to the office and kissed her. The couple seconds of silence after that gasp-inducing moment made for one of the best teases the show has ever aired. Fans were in for a long summer.
Best Line: ”Sometimes I don’t put Michael through [on the phone] until he’s already said something. I look at it as a practice run for him. He usually does better on the second attempt. ” —Pam Beesley, on Michael Scott’s phone manner
1. ''The Dundies''
Season 2, episode 1
Aired: Sept. 20, 2005
This fan-favorite episode 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 un-P.C. imitations and lame jokes to the too obvious mancrush on Ryan (B.J. Novak). As ever, the staffers’ pain was our utter pleasure. You never forget your first Dundies — or the excited scream viewers let out when engaged Pam drunkenly kissed Jim.
Best Line: ”You know what they say about a car wreck, where it’s so awful you can’t look away? The Dundies are like a car wreck that you want to look away from but you have to stare at it because your boss is making you.” —Pam Beesley