The 20 Best Episodes of ‘The Office’

This year, the iconic NBC sitcom The Office turned 20 years old. Originally based on the UK series of the same name, the mockumentary has only grown in esteem since its conclusion in 2013, even inspiring multiple podcasts from actors on the show. It might be one of the most universally beloved shows out there; in 2020, it was reportedly the most-streamed show by far on Netflix, evident from the sheer number of dating app profiles seeking “the Jim to my Pam.”

Here are the 20 best episodes of The Office, available to pop on anytime for a reliable mood boost—or even a comforting sleep aid, for those who have already binged the show multiple times.

Season 1, Episode 2: “Diversity Day”

The Office truly took off when it established its own identity in Season 2. But the six episodes of Season 1 aren’t without their moments, especially after the very first one, a direct Americanized adaptation of the original British pilot. The follow-up, the first episode to feature original writing, gets huge laughs out of Michael Scott’s ignorance when an inappropriate recitation of Chris Rock’s famous “N—-s vs. Black People” routine leads to a mandatory diversity training seminar headed by Larry Wilmore’s sensitivity trainer (hideously co-opted by Michael, of course).

Season 2, Episode 1: “The Dundies”

Beyond the iconography of Pam getting drunk and sloppy and giving a speech at Chili’s before smooching Jim, the beginning of Season 2 is a significant turning point for the show. The reconfigured version had brighter lighting, more of the supporting cast, and a new, more empathetic take on Michael, no longer quite as villainous and unpleasant as in the first season. The new and marginally improved regional manager gets his time to shine at the annual office awards show in this fan-favorite episode, flopping as MC until he gets some drunk encouragement from his favorite receptionist.

Season 2, Episode 11: “Booze Cruise”

A cruise doubling as a party and a leadership training exercise—it’s a pretty classic Michael Scott idea, and his petty jealousy of the ship captain is a very Michael Scott reaction. But by far the most memorable Michael moment of this episode is his final conversation with Jim, when the latter confesses his feelings for a still-engaged Pam. Michael is characteristically oblivious hearing this for the first time, but his response is an all-time moment, telling Jim that “engaged ain’t married” and urging him to “never, ever, ever give up.”

Season 2, Episode 12: “The Injury”

One of the early standout episodes rests on a singularly hilarious hypothetical: what if Michael burned his foot on a George Foreman Grill? Watching him navigate this terrible, horrible, no good, very bad day never gets old, especially with the obvious enjoyment everyone else derives from the incident. And when his self-pity about the injury turns into a weird possessiveness upon the discovery of Dwight’s very real concussion (from a car crash on his way to rescue Michael, mind you), the episode reaches another level.

Season 2, Episode 22: “Casino Night”

Season 2, probably the show’s very best, is bookended by two episodes that feature Jim and Pam locking lips, and ends on a cliffhanger following Jim’s confession of his love for Pam and their first real kiss in the Steve Carell-penned finale. Though it would take another season for the pair to officially get together—Pam is still engaged, and Jim requested a transfer to the Stamford branch—this is one of the biggest and most triumphant moments of the show. And it’s not the only romantic development of the supersized episode, with Jan pining for Michael at the charity casino night where he brought another date: his realtor Carol (played by Nancy Walls, Carell’s real-life wife).

Season 3, Episode 9: “The Convict”

Prison Mike, Michael’s purple-bandana’d ex-convict alter ego, is easily one of his most memorable and silly personas in a show full of them. Like most of Michael’s gambits, this is a mostly well-intentioned effort, originating with an unnecessary attempt to stand up for Martin Nash (Wayne Wilderson), an employee who did time for insider trading. But it becomes much more about proving to his employees that prison isn’t actually better than the office, overreacting to their jests by improvising about how “The worst thing about prison was the Dementors.” It’s no surprise Martin quits by the end.

Season 3, Episode 10 and 11: “A Benihana Christmas”

Arguably the show’s best Christmas outing (with Season 2’s “Christmas Party” at a close second), this double-length installment revolves around two rival Christmas parties at the office, one thrown by Angela’s Party Planning Committee and one organized by Pam and Karen, whose new friendship freaks Jim out. It also features Michael’s post-breakup trip to Benihana with Andy, Jim, and Dwight, which ends with Michael marking one Asian waitress with a Sharpie back at the office to differentiate her from Andy’s date. Problematic to be sure, but also a very in-character move for an ignorant buffoon.

Season 3, Episode 19: “The Negotiation”

Michael and Darryl are one of the most underrated Office pairings, and it’s a delight to watch them work together to secure raises. But this is also the episode that officially closes the door on Pam and Roy forevermore with Roy’s attempt to attack Jim for kissing Pam back in “Casino Night”—a fight that ends before it can even begin when Dwight pepper-sprays him. Part of the joy of the episode comes from Jim’s rare efforts to show his sincere gratitude to Dwight, who refuses to accept his praise.

Season 3, Episode 20: “Safety Training”

Michael’s trip to the rooftop to illustrate depression and suicidal ideation yields the great “Dwight, you ignorant slut” line, but it’s also just funny to watch him cope with his hurt pride after the warehouse guys make fun of an office safety session. This episode also includes some other standout moments, like a watermelon bouncing onto Stanley’s car and Dwight “shunning” Andy.

Season 3, Episode 23: “Beach Games”

Michael’s beach competition to choose a potential successor isn’t just enjoyable for fans of Survivor, on which the games are based; it’s a classic episode, especially remembered for the sumo wrestling and the turn in the Jim/Pam/Karen love triangle. Pam running barefoot across hot coals is impressive, but her biggest act of growth is the unusually candid speech she delivers in front of her coworkers, taking them to task for missing her art show and blaming Jim for the cooling of their friendship.

Season 3, Episode 24 and 25: “The Job”

The episode that finally brings Jim and Pam together for good! The finale also gives us a glimpse of what Dwight’s tenure as regional manager would look like, complete with motivational Schrute Bucks, and sets up Ryan’s new role in Season 4, when he gets offered Jan’s old job. But the standout moments here are all about the romance, especially that interrupted confessional when Jim asks Pam out.

Season 4, Episode 1 and 2: “Fun Run”

After three seasons of Jim and Pam’s tantalizing will-they-won’t-they, it’s quite refreshing to watch them secretly date in the Season 4 premiere—though that storyline can’t quite beat the hilarity of Michael fracturing Meredith’s pelvis by accidentally hitting her with his car in this episode, then hosting a charity 5k to fight rabies. Dwight telling Angela he euthanized her cat Sprinkles is a highlight, and you won’t soon forget the image of Andy’s nipples bleeding through his shirt.

Season 4, Episode 12: “The Deposition”

Michael Scott can be a terrible person, but there’s a reason his relationship with Jan is so good for the show: her cruelty brings out our empathy for him, like during the deposition where she forces him to be a witness against Dunder Mifflin. To bolster her wrongful termination case and prove that she had no prior relationship with Michael before they disclosed it, she goes so far as to submit her boyfriend’s personal diary—and he finds out she gave him a terrible performance review after they started dating. (An all-time quote: “You expect to get screwed by your company, but you never expect to get screwed by your girlfriend.”) The subplot of Kelly trash-talking Jim’s ping pong skills is pretty great, too.

Season 4, Episode 13: “Dinner Party”

Up there with “Scott’s Tots” as the most difficult-to-watch episode of The Office, this cringey masterpiece takes place during a couples’ dinner at Michael’s condo. There, all of his and Jan’s relationship issues are lain bare, with Michael in the role of victim (albeit a pathetic, unselfaware one) to Jan’s control issues and selfishness. Whether it’s Michael showing off his tiny plasma TV and describing a wine’s “oaky afterbirth,” Jan mistaking Pam for an ex and competitor for Michael’s heart, or Dwight bringing a former babysitter as a date, everyone is firing on all cylinders here.

Season 4, Episode 18 and 19: “Goodbye, Toby”

A going-away party for Toby before he leaves for Costa Rica? Jim planning to propose to Pam, only to get preempted by Andy’s proposal to Angela? Ryan getting arrested for fraud? This season finale has it all, though the most consequential development is the introduction of the charming HR rep Holly Flax (Amy Ryan), the future love of Michael’s life.

Season 5, Episode 14 and 15: “Stress Relief”

Chances are you’ve seen the incredible cold open from this two-part episode clipped on your social feed sometime in the last decade: Dwight “simulating” an office fire as a safety demonstration. It’s a huge episode all around for Dwight, who famously destroys a CPR dummy and wears its face, Hannibal Lecter-style, during a training session. Much of this episode also revolves around Michael’s comedic roast of himself, which goes exactly how you’d expect when his employees enjoy it a little too much.

Season 5, Episode 25: “Broke”

The last three or four seasons of The Office would struggle to keep the dynamics fresh, but Season 5 staved off that issue with the great Michael Scott Paper Company arc, a stretch of episodes that injected new energy into the show by introducing a new villainous manager named Charles Miner (Idris Elba). In this conclusion to the arc, Michael scores one of his biggest wins ever, displaying some actual business acumen by successfully pressuring David Wallace into hiring back him, Pam, and Ryan. Supremely satisfying.

Season 5, Episode 28: “Company Picnic”

Another seriously consequential season finale promising significant change while delivering big laughs. Pam finds out she’s pregnant; Michael displays some ugly but hilarious jealousy of Holly’s boyfriend A.J.; Michael and Holly perform a skit (“SlumDunder Mifflinaire”) that accidentally reveals the Buffalo branch is closing due to the recession. A pathos-heavy episode—but an important one.

Season 7, Episode 19: “Garage Sale”

The Office in treacly mode isn’t always the show at its best, but this episode sets up Michael moving to Colorado in the sweetest, most deserved way, ending with his pitch-perfect proposal to Holly and the shocking announcement of his departure. That proposal makes for one of the most romantic and tear-jerking sitcom scenes of all time, up there with Ben Wyatt and Leslie Knope—and the lighter titular subplot, with Jim pranking Dwight by replacing the supposed “miracle legumes” with fully grown plants, offers a nice counterbalance.