The 25 Most Hilarious Episodes of The Office

Article Overview

The funniest episodes of The Office showcase the show's ability to wring laughs from uncomfortable scenarios and increasingly awkward situations.

The workplace sitcom of The Office is filled with unforgettable and highly quotable moments thanks to holiday celebrations, new distractions, and exciting adventures outside of Dunder Mifflin. The comedy truly comes to life when Michael Scott's delusional mind and outrageous antics steal the show, delivering uproarious, cringe-worthy, and side-splitting moments.

The Office episodes that are considered the funniest provide a clear glimpse into what fans adore about the show. As one of the most beloved comedy series in television history, the American remake of The Office is not only highly regarded, but also highly rewatchable. Even after binge-watching all nine seasons, fans can easily restart from the beginning without hesitation. Though the show is able to evoke emotions and tug at heartstrings, it is the humor that continues to attract fans, particularly showcased in the funniest episodes of The Office.

These episodes encompass various holiday celebrations that inevitably result in chaos, the new distractions that Michael introduces to the workplace, and even some notable adventures that take place beyond the confines of Dunder Mifflin. These particular episodes stand out as they deliver the most comical moments and memorable lines from this workplace sitcom. While some episodes hold a special place in fans' hearts for various reasons, others are simply cherished for their comedic brilliance in The Office.

25. Christmas Party

Season 2, Episode 10

Although The Office has had some amazing Christmas episodes, the very first one remains unbeatable. After a year of layoffs and budget cuts, Michael is determined to make this year's holiday festivities unforgettable, even though corporate has banned alcohol. Unsurprisingly, Michael ends up causing chaos at the party by transforming the simple Secret Santa gift exchange into a nerve-wracking Yankee Swap game.

The episode brings together a plethora of yuletide amusement, skillfully blending the show's ability to extract laughter from progressively awkward situations. It culminates in an enjoyable finale, wherein Michael resolves to regain everyone's favor through the medium of alcohol. This episode's exceptional writing earned it an Emmy nomination and solidifies its status as a perennial holiday season favorite.

24. Gossip

Season 6, Episode 1

In any office space, gossip is inevitable, but it becomes significantly worse when Michael Scott becomes involved. In this episode, Michael, feeling left out of the latest news in the Scranton office, embarks on a search for the juiciest gossip he can find. Accidentally exposing Stanley's affair, he attempts to spread misinformation in order to cover it up.

Michael's endless rumors about everyone in the office provide plenty of hilarious moments, particularly when Andy starts to question his own identity after a rumor circulates that he is gay. This chaotic situation created by Michael leads to a laugh-out-loud conclusion. Showrunner Michael Schur received an Emmy nomination for writing this episode.

Stream The Office on Peacock

23. Phyllis' Wedding

Season 2, Episode 10

Wedding episodes on The Office have always been entertaining, and while "Phyllis's Wedding" may not be the most unforgettable among them, it definitely delivers the most laughs. The comedy ensues when Michael is tasked with assisting in the ceremony, allowing his ego to take control. However, when he realizes his role is not as prominent as he anticipated, he throws a tantrum like a child. Witnessing Michael's immaturity can be cringeworthy, yet undeniably hilarious. Additionally, there is a humorous subplot where Pam gradually realizes that Phyllis simply replicated the plans from her abandoned wedding with Roy.

22. Diversity Day

Season 1, Episode 2

The show's first season had a slow start, struggling to emerge from the shadow of its British counterpart and not fully realizing its characters. However, the second episode highlighted the show's immense potential. The premise of Michael Scott leading diversity sensitivity training was a perfect setup, displaying Michael's hilariously oblivious nature and the show's expert execution of cringe-worthy comedy. It would be painful to watch if it wasn't so funny, although the episode's controversial and offensive aspects hold it back.

21. The Coup

Season 3, Episode 3

In "The Coup," Dwight, who has always been Michael's most loyal employee, finds himself conflicted as his ambition drives him to compete for the manager position. However, when Michael discovers Dwight's betrayal, he concocts an elaborate revenge scheme. Throughout the episode, comedic moments abound as both Dwight and Michael exaggerate the significance of their power struggle. From Dwight's peculiar encounter with Jan to Michael's scrutiny of Dwight's dentist appointment excuse, the truth eventually surfaces, resulting in an entertaining clash between these unforgettable characters.

20. Goodbye, Toby

Season 4, Episode 14

The Office's portrayal of Michael's animosity towards Toby has become a beloved recurring joke among fans, so there were high hopes for how Toby's farewell party would be handled. This particular episode also marks the introduction of Holly Flax, resulting in some heartwarming moments as she and Michael unexpectedly hit it off. Packed with surprises like a proposal, an unexpected return by Jan, and a cliffhanger revelation, the highlight of the episode lies in Michael's long-awaited satisfaction as he bids farewell to his nemesis, complete with a side-splitting exit interview.

19. Threat Level Midnight

Season 7, Episode 17

Fans of The Office are in for a special treat with one of the most hilarious episodes in the series. This particular episode brings back a long-standing gag that finally reaches its satisfying conclusion. After years of discovering the script for Michael Scott's spy movie, Threat Level Midnight, the employees of Dunder Mifflin come together to watch the finished product. This episode offers a delightful glimpse into Michael's delusional mind, showcasing his unwavering belief in the movie's potential greatness. Additionally, viewers will enjoy seeing the cast members in various roles within the film, with some exciting cameos from former cast members.

18. The Fight

Season 2 Episode 6

The dynamic between Michael and Dwight has long been a standout aspect of the show. While they typically collaborate, "The Fight" breaks the mold as they go head-to-head in a bid for the title of the office's toughest individual. The ultimate fight scene is hilariously lackluster, but the episode is rife with memorable moments leading up to it. From Jim's prank of relocating Dwight's desk to the bathroom to Michael's tendency to procrastinate, it delivers a mix of laughter and excitement.

17. The Negotiation

Season 3, Episode 19

Michael and Jan's romantic relationship took an unexpected turn, gradually becoming increasingly bizarre. This transformation becomes evident in the episode "The Negotiation," where Michael finds himself compelled to testify during Jan's lawsuit negotiation. One of the Office's finest moments emerges when it fully embraces cringe-inducing comedy. This particular episode delivers those uncomfortable laughs as Michael endures a series of embarrassing moments throughout his deposition, including the revelation of his diary entries which reveal his infatuation with Ryan.

16. Business School

Season 3, Episode 16

Some of the most hilarious episodes of The Office revolve around Michael's opportunities to showcase his acting skills. In the episode "Business School," he is invited to speak to Ryan's class, hoping to inspire a new generation of professionals. However, instead of imparting valuable wisdom, Michael ends up tearing out a student's textbook and playfully throwing candy bars at the class. The situation becomes even more amusing when Dwight tries to catch a loose bat in the office, while Jim playfully teases him about turning into a vampire.

15. Conflict Resolution

Season 2, Episode 21

In the episode titled "Conflict Interest," the ongoing pranks and clashes between Jim and Dwight reach their climax when Dwight realizes that his numerous complaints over the years have never been relayed to the higher-ups. Responsibility falls on Michael to resolve the conflicts, but his efforts only exacerbate the situation. Fans are treated to a meeting where some of Jim's most memorable pranks are discussed, resulting in a comical unveiling of all the pent-up grievances among office colleagues.

14. Safety Training

Season 3, Episode 20

Despite his constant buffoonery, Michael is an individual who deeply craves respect and is willing to go to great lengths in order to obtain it. The episode "Safety Training" serves as a prime example of Michael's burning desire for validation. Following an incident in the warehouse (caused by none other than Michael himself), the entire office is required to undergo safety training. This particular scenario provides the perfect opportunity for Michael to showcase his immaturity, all while becoming increasingly self-conscious about his cushy position. The climactic moments, wherein Michael contemplates jumping off the roof to highlight the hazards of office life, encapsulate the pinnacle of Michael's absurdity.

13. Scott's Tots

Season 6, Episode 12

Despite his occasional lapses in judgment, Michael sometimes shows a genuine sense of compassion. This is evident in "Scott's Tots," an episode from The Office, where Michael is confronted with the consequences of a well-intentioned yet impractical promise he made to a group of disadvantaged students. He had assured them that he would fund their college tuition upon graduation, only to realize later that his financial situation cannot meet this commitment. The ensuing events unfold with a mix of cringe-worthy moments and hilarity, making it one of the most memorable episodes in the series.

12. Broke

Season 5, Episode 25

Michael's blind ambition and poorly thought-out ideas never fail to create comedic gold, especially when he finds himself as the underdog. In the episode "Broke," we witness Michael, Pam, and Ryan forming their own company, the Michael Scott Paper Company, which surprisingly becomes a competitor to Dunder-Mifflin. However, their success is short-lived as financial troubles start plaguing them. The real entertainment lies in the dynamic between Michael, Pam, and Ryan, who surprisingly work well as a team. Additionally, Dwight's attempts to bring down the Michael Scott Paper Company and Jim's continuous interference provide great moments of humor.

11. Booze Cruise

Season 2, Episode 11

Many of the series' best episodes involve the Dunder-Mifflin employees venturing outside the office and embarking on exciting adventures. "Booze Cruise" is yet another one of Michael's team-building escapades, as the team sets sail for an enjoyable evening on the water. The episode perfectly showcases Michael's knack for embarrassing himself and his inability to recognize when to stop. While he attempts to deliver a motivational speech, everyone else is focused on having a good time. The climax occurs when he mistakenly announces that the ship is sinking, causing widespread panic.

10. Casino Night

Season 2, Episode 22

"Casino Night" serves as a thrilling conclusion to the show's second season, forever etching itself in viewers' minds as the episode where Jim finally confesses his feelings to Pam. However, it is not just this heartfelt moment that makes the episode memorable. The casino backdrop provides the perfect stage for numerous hilarious situations, such as Kevin's comical failure at becoming a poker master, Creed's mischievous acts of thievery, and Michael's laughable attempts at bluffing. Additionally, the inclusion of Michael bringing two women as his dates adds a layer of awkwardness and creates a captivating love triangle.

9. Customer Survey

Season 5, Episode 7

While Jim and Dwight are famously renowned for their rivalry, their dynamic as allies can be even more entertaining. When both of them receive exceptionally negative performance reviews, they unexpectedly find themselves on the same team. The banter shared between these two characters becomes one of the standout elements of the show. Even in their alliance, Jim never misses an opportunity to play pranks on Dwight, like hilariously imitating a sales call. Additionally, the show offers amusing moments when Jim discreetly communicates with Pam through his minuscule Bluetooth earpiece, creating confusion and amusement for Dwight.

8. The Convict

Season 3, Episode 9

The introduction of new characters from the Stamford branch to the Scranton branch brought both excitement and challenges. Unfortunately, one of the new employees, Martin, turns out to be a convicted felon, which causes panic for Michael. This episode showcases the extremes of Michael's personality. Initially, he tries to handle the situation confidently, but only manages to make it worse. As the office starts joking about prison being a better option than Dunder-Mifflin, Michael's insecurity takes over and turns the situation into a disaster. This is the episode where the world gets to meet "Prison Mike," one of Michael's funniest characters.

7. The Surplus

Season 5, Episode 10

Despite Michael occasionally getting things right, he often manages to make mistakes. Once he discovers a budget surplus, Michael involves the entire office in deciding the most beneficial allocation for the funds. However, his attitude changes when he realizes he can personally benefit from the surplus. This particular episode highlights the collaborative dynamics of the office, as each individual proposes their own ideas on how to utilize the money. Consequently, tensions arise within the office, even between Jim and Pam.

6. Beach Games

Season 3, Episode 23

This show never fails to entertain, as seen in another instance where the office's eccentric characters take center stage. After discovering his potential promotion, Michael comes up with an unconventional way to select his successor – by creating a series of challenges at the beach. The episode is filled with hilarious moments that will have you in stitches. From a comical hot dog eating contest to Andy floating away wearing a Sumo suit, and even Dwight's painful attempt at walking across hot coals. It proves that the show can be just as humorous when it ventures outside the office environment.

Editor's P/S

As a long-time fan of The Office, I can confidently say that the show's funniest episodes are those that showcase Michael Scott's unique brand of humor. Whether he's making inappropriate comments, getting himself into awkward situations, or simply trying to be funny, Michael always manages to make me laugh. Some of my favorite episodes include "The Injury," "The Dinner Party," and "Stress Relief."

One of the things I love most about The Office is that it's a show that can be enjoyed by people of all ages. The humor is clever and relatable, and the characters are well-developed and likable. I can always count on The Office to give me a good laugh, and I'm sure it will continue to be one of my favorite shows for years to come.