The Office (US) is not only one of the most beloved television comedies of all time, but it’s also one of the most rewatchable. Even after binging all nine seasons of the show, fans can turn around and start again from the beginning. And while the show certainly knows how to pull at the heartstrings and can bring a tear to the eye, it’s the laughs fans keep coming back for.
The antics of the employees at Dunder-Mifflin remain hilarious no matter how many times fans watch them. There are countless episodes that have some of the funniest moments and most quotable lines on television. So while there are some episodes fans hold dear because of how special they are, some stand out as the flat-out funniest episodes of The Office.
Updated on February 6th. 2022 by Colin McCormick: Despite the fact that it wasn’t a huge ratings juggernaut when it was on the air, The Office is perhaps the most rewatchable show on streaming services these days.
With eleven seasons of misadventures courtesy of Michael Scott and the people at Dunder Mifflin, there are always lots of laughs in the funniest Office episodes for fans to look back on. Out of the many stellar episodes, there are those classic ones that can always bring out the joy no matter what kind of mood the audience is in.
Threat Level Midnight (Season 7, Episode 17)
This episode of The Office feels like a special treat to fans as an intriguing gag from long ago gets a wonderful payoff. Years after finding a script for Michael Scott’s spy movie Threat Level Midnight, the employees of Dunder Mifflin gather to see the finished product.
The episode is a wonderful glimpse inside Michael’s delusional mind as he actually thought this ridiculous movie would turn out to be good. It is also a lot of fun to see the various ways the cast is used in the film, including some fun cameos from former cast members.
The Fight (Season 2 Episode 6)
The relationship between Michael and Dwight has always been one of the highlights of the show. While they are usually seen working together, “The Fight” is a rare instance when they are against each other as they each attempt to claim the title as the office’s toughest person.
The climactic fight is hilariously pathetic but the episode is filled with a lot of terrific moments leading up to that. From Jim’s prank of hiding Dwight’s desk in the bathroom to Michael’s procrastination, it delivers laughs and action.
The Negotiation (Season 3, Episode 19)
The romantic relationship between Michael and Jan started out as unexpected and then just got really strange over time. This is really solidified in the episode “The Negotiation” where Michael is forced to testify at Jan’s lawsuit negotiation.
The Office is often at its best when it is embracing the most cringe-worthy comedy. This episode delivers those uncomfortable laughs as Michael is continuously embarrassed during his deposition, including the reading of his diary with detailed entries about his man-crush on Ryan.
Business School (Season 3, Episode 16)
It seems like some of the funniest episodes of the show are whenever Michael is given the opportunity to put on a big performance. In “Business School,” he is invited to be a guest speaker at Ryan’s class where he hopes to inspire a new generation of professionals.
Seeing Michael spout what he thinks are pearls of wisdom but actually just involves him ripping out a student’s textbook and throwing candy bars at them is great fun. To make it even better, Dwight deals with a bat lose in the office while Jim convinces him that he is becoming a vampire.
Conflict Resolution (Season 2, Episode 21)
The endless pranks and battles between Jim and Dwight come to a head in the episode “Conflict Interest” as Dwight realizes that all of his complaints over the years went unreported to corporate. It is then up to Michael to squash the beefs yet only succeeds in making things worse.
Fans are treated to a scene in which some of Jim’s best pranks are discussed in a meeting. It also leads to all of the inner office grievances being put out in the open with some hilarious results.
Safety Training (Season 3, Episode 20)
Despite what his constant buffoonery might suggest, Michael is someone who craves respect and will go to great lengths to get it. No episode better displays that burning desire in Michael than “Safety Training”.
After an accident in the warehouse (caused by Michael, of course) the entire office must undergo safety training. The premise is the perfect setup for Michael to show off how immature he is while also getting self-conscious about his cushy position. The final moments of Michael planning to jump off the roof to prove the dangers of office life shows Michael at his most ridiculous.
Scott’s Tots (Season 6, Episode 12)
Sometimes Michael’s heart can really be in the right place even if his brain is not. In “Scott’s Tots”, Michael is forced to confront his biggest mistake as he promised a class of underprivileged students he would pay for their tuition when they graduated from high school.
Obviously, when the time comes, Michael is far less rich than he thought he would be and can’t keep his promise. What follows is one of the most cringe-inducing and awkwardly hilarious episodes in the entire series.
Broke (Season 5, Episode 25)
It’s fun seeing Michael as an underdog as his blind ambition mixed with his ill-conceived ideas tend to make comedy gold. “Broke” follows Michael, Pam, and Ryan at their newly established Michael Scott Paper Company. While the business has become a competitor to Dunder-Mifflin, Michael soon finds they are going broke.
What is most fun about this episode is the interactions between Michael, Pam, and Ryan as this new team who work surprisingly well together. There are also some great moments with Dwight trying to bring down the Michael Scott Paper Company and Jim continuously getting in his way.
Booze Cruise (Season 2, Episode 11)
It seems that many of the best episodes of the series involve all the Dunder-Mifflin employees getting out of the office setting and going on an adventure. “Booze Cruise” is another of Michael’s team-building activities as the team heads out for a fun night on the water.
The episode is another great example of Michael making a fool of himself and not knowing when to quit. He tries to make a motivational speech as everyone else tries to party. It all culminates in him announcing the ship is sinking and causing massive panic.
Casino Night (Season 2, Episode 22)
“Casino Night” is an eventful finale episode to the second season of the show. It is largely remembered as the episode in which Jim finally tells Pam how he feels but there are plenty of hilarious moments to remember as well.
The casino setting for the episode is the perfect setting for so many funny scenarios, from Kevin’s failed attempt at being a poker all-star to Creed’s constant stealing to Michael’s bad “bluffing”. There’s also some great stuff involving Michael’s love triangle with Jan and Carol.
Customer Survey (Season 5, Episode 7)
As great as Jim and Dwight are as enemies, they are sometimes even more entertaining as allies. After they both get unusually poor performance reviews, they find themselves in the odd position of being on the same side.
The back-and-forth between these two is one of the highlights of the show. Even while allies, Jim can’t help but mess with Dwight in a hilarious mock sales call. There are also some very funny moments with Jim’s super tiny Bluetooth earpiece he uses to discreetly talk to Pam and, of course, confuse Dwight.
The Convict (Season 3, Episode 9)
When the merger of the Stamford branch into the Scranton branch introduced some fun new characters and brought some characters back, it wasn’t all smooth sailing. In this episode, Michael panics at the news to learn a new employee, Martin is a convicted felon.
This is episode is a great display of the wild extremes of Michael. First, his confident side tries to make things better – while making it worse, obviously. Then when the office begins joking that prison sounds better than Dunder-Mifflin, the insecure Michael turns it into a disaster. It’s the episode the world is introduced to “Prison Mike”, one of his funniest characters.
The Surplus (Season 5, Episode 10)
Even when Michael does something right, he manages to do something wrong. After discovering a surplus in the budget, Michael has the office trying to decide where the money would best be spent. That is until he learns that he can keep some of the money for himself.
This is one of those episodes that makes great use of the whole office. Everyone has their own ideas about how to spend the money, leading to the office division in the office, even among Jim and Pam.
Beach Games (Season 3, Episode 23)
Another great example of how funny this show can be is when they utilize every bizarre character in the office. After learning he is being considered for an executive role, Michael decides the best way to choose his successor is with a series of challenges – while at the beach.
There are so many laugh-out-loud moments in this episode. From the hot dog eating contest to Andy floating away in a Sumo suit to Dwight’s painful failure to walk across the coals. It proves the show can be just as funny when they leave the office setting behind.
Stress Relief (Season 5, Episode 14)
This episode solidifies its place on this list for its cold-open alone. When Dwight gets fed up with the lack of interest in his office fire drills, he goes to extreme measures to prove a point. Chaos and hilarity ensue.
If that was the only highlight of the episode, it would already be one of the funniest, but there are so many more laughs in this two-parter. There are also great moments during the CPR course and the revelation that Michael is the cause of everyone’s stress. That’s not even to mention the roast of Michael Scott in part two.
Money (Season 4, Episode 7)
This episode is a rare example of how the subplot which doesn’t involve Michael Scott is actually the highlight of the episode. Certainly, the main story which follows Michael’s struggle to balance a second job and deal with his money problems does have some great laughs. But it is Jim and Pam’s overnight getaway to Schrute Farms that makes this a classic.
The truly bizarre and over-the-top lifestyle of Dwight is always funny and it’s great to see some other characters finally confronted with just how weird it is. There are some sweet moments of feeling sorry for heartbroken Dwight, but they never outweigh the absurd comedy.
Diversity Day (Season 1, Episode 2)
The first season of the show took a little while to get going. It was still struggling to move out of the shadow of the British version and the characters were not yet fully realized. However, the second episode showed just how much potential the show had.
The concept of Michael Scott doing diversity sensitivity training is just the perfect set-up. It showcased the hilarious ignorance of Michael as well as the cringe-worthy comedy the show did so well. It would be painful to watch if it wasn’t so funny.
The Dundies (Season 2, Episode 1)
The Dundies have been a recurring feature of the show, but nothing is as memorable as the first introduction to Michael’s glorious awards show. Michael is at his funniest when he is in his entertainer role. Not only does he often make a disaster of things but he seems oblivious to how little people are interested.
This is also a great episode for those early Jim and Pam days as Pam gets a little tipsy during the ceremony at Chili’s. It’s not too often she gets the opportunity to be the out-of-control character and Jenna Fischer clearly has fun with the moment.
Dinner Party (Season 4, Episode 13)
The show seems to take pleasure in making the audience sit in the most uncomfortable situations imaginable. And what could be more uncomfortable than an intimate dinner party with the boss and his girlfriend?
It turns out that Michael is just as awkward in his home life as he is in the office and his guests are treated to a glimpse at his very uncomfortable relationship with Jan. There are so many great gags like Michael’s “flat-screen” television and his unusual sleeping arrangement with Jan. Fans will want to escape the situation, but will also find it too entertaining to look away from.
The Injury (Season 2, Episode 12)
Despite being a sweet and caring person on occasion, it can be really fun to laugh at Michael Scott. That might be because, when he’s not being sweet, he’s often an attention-seeking man-child.
This episode is the perfect example of why Michael is always a fun butt of the joke. After burning his foot in a breakfast-in-bed mishap, Michael becomes insufferable and demanding to everyone around him. Aside from the ridiculous injury and Michael’s childish behavior, the episode gets several laugh-out-loud moments from a concussed Dwight. This episode was the peak of Michael, and the show, in terms of comedy.
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