The Office is one of television's best comedies, and a lot of this is due to the hilarious times characters in the show messed up. Michael Scott is certainly the gold standard for characters who made epic blunders, but most everyone at the Dunder Mifflin Scranton Branch is guilty of at least one major error.
After revisiting a number of episodes with my Peacock Premium subscription, I believe I've whittled down a list of 30+ different moments a character on The Office messed up. Surprisingly, none of these moments are Dwight falling for one of Jim's pranks, which really says something about how wild things got on the sitcom.
Michael Grilling His Foot Making Bacon
Loving to wake up to the smell of bacon in the morning is not worth a potential burn on your foot, though Michael Scott said otherwise in "The Injury." Planting his foot on a George Foreman grill next to his bed might be one of the most memorable Michael blunders of all time.
Eating Todd Packer's Cupcakes
Todd Packer was perhaps one of the shadiest characters of The Office, and while we didn’t need any evidence by the time he was finally fired in "The Farm", his final act really drove the point home. Packer offered cupcakes to the staff before leaving, only to later reveal on camera that he laced the cupcakes with drugs that had a variety of affects on those who ate them.
Roy Attacks Jim At Work
Roy’s attempt to win back Pam was a rough arc to watch, but it came to an upsetting end in "The Negotiation" when he rushed Jim at the Dunder Mifflin office and tried to attack him. He was thwarted by Dwight, who pepper-sprayed him. Roy was fired later, and it effectively ended whatever small chance he had at salvaging his relationship with Pam.
Dwight Does A Realistic Fire Drill
“Stress Relief” features the most hilarious and preventable screw-up of The Office, when Dwight decided to stage a fire drill that involved actual fire, among other traps. Stanley ended up having a heart attack because of the ordeal, so it’s hard not to look back on this one as one of the bigger times someone messed up.
Michael Dating Jan
If there were an award for the most toxic relationship in television sitcom history, I think Michael and Jan would have to be in top contention to win. There was always a question of whether or not Jan loved Michael for who he was, or because he was around at a rough time in her life. We could debate that all day, but between the memories of the awkward dinner party to her surprise pregnancy, I think we can agree both would’ve been better off not dating.
Michael Starts Scott’s Tots
"Scott's Tots" is infamous for The Office fans, and is the top-ranked cringe-worthy episode on CinemaBlend. Michael had to face the empty promise he made to a bunch of underprivileged children to fund their college education in an absolutely brutal episode of television. Just writing about it makes me feel ill.
Andy Accidentally Dates A Highschooler
Andy Bernard made a lot of mistakes when it came to love on The Office, but perhaps one of his biggest missteps came in "Product Recall" when he happened upon his girlfriend while visiting a high school on business with Jim. Fortunately, his relationship with the part-time frozen yogurt chef never went too far, minus the fact they knocked over a mailbox with her friends.
The Yankee Swap Decision
"Christmas Party" is surely on many people's list of the best Christmas episodes of The Office, but it's also top of the list for someone messing up. Michael messed up by buying the video iPod that far-exceeded the $20 limit for Secret Santa. Jim messed up by giving Pam a gift that might've been a touch too personal, and Phyllis messed up by thinking Michael would want that oven mitt. Let's not forget Kelly also kissed Dwight, which I'm sure she also regretted.
Phyllis Letting Michael Be A Part Of Her Wedding
While it all worked out for the better in "Phyllis' Wedding," I'll never for the life of me understand why Phyllis asked Michael to have any role in her wedding. Sure, he found Uncle Al (unintentionally), and made a happy day less stressful, but does that really make up for the outbursts during the ceremony, or the crude remarks during the wedding toast? I'd say no, and I'd reckon Bob Vance from Vance Refrigeration would say the same.
Angela Agreeing To Let A Duel Decide Who She'll Stay With
Angela's affair with Dwight led to him having a duel with Andy, but it was completely unnecessary. The smart decision would’ve been for her to just leave Andy for Dwight, as that was where her true affections were. Instead, she allowed them to fight and both men discovered she betrayed them in various ways. By the end she had neither, so it’s hard to argue this wasn’t a mistake on her end.
Deangelo Hospitalized Dunking A Basketball
Deangelo Vickers had a short run as the branch manager at Dunder Mifflin. This was due to his decision in "The Inner Circle" to try and dunk a basketball to inspire the staff, which ended up collapsing the hoop. Deangelo was rushed to the hospital and despite a brief return wrapped in bandages, was left comatose. It's later stated that Vickers is brain dead as a result of the incident, which remains one of the roughest exits for a character on the show.
David Wallace Transferring Holly to Nashua
After witnessing them kissing in "Crime Aid," David Wallace made the decision to transfer Holly away from Scranton, to Nashua. The move ended up putting a big wedge between David and Michael, and would only cause further tension between them down the line.
Kevin Should’ve Gotten Tupperware To Secure His Chili
The iconic chili cold-open in "Casual Friday" has driven me up a wall for years. Why did Kevin bring his chili to the office in the pot he cooked it in? Why would he not have used some kind of sealable container? If he had, perhaps actor Brian Baumgartner wouldn't have been caked with the smell of chili, which is just one of the interesting facts from The Office fans may not know.
Ryan Shouldn’t Have Microwaved That Cheese Pita
Ryan had a lot of missteps in his career, and one could argue it all began in "The Fire." His mistake of using the wrong setting for his cheese pita in the toaster oven and causing a smoke-related evacuation made him a target of Dwight, and ultimately dubbed him "Fire Guy."
Ryan Should’ve Checked The Date Before Hooking Up With Kelly
Ryan never thought of having a serious relationship with Kelly at the beginning of The Office, and she might've believed that had it not been for one major error. Ryan hooked up with Kelly on Valentine's Day eve, which began a years-long on-and-off-again relationship that ultimately worked out. It's not quite the love story that Jim and Pam had, but hey, it worked out.
Jim Shouldn't Have Accepted Dwight's Challenge To A Snowball Fight
Jim gets the better of Dwight 90% of the time they feud, but he should've known something like a snowball fight wasn't his bag. With no prep time, he strolled out to have a snowball fight, only to get obliterated by an overly prepared Dwight. It was nice to see Dwight get a win for once!
Michael Shouldn’t Have Carbo Loaded Before The Rabies Awareness Race
It's one thing to refuse water during a rabies awareness race, and it's quite another to "carbo load" on fettuccine alfredo moments before running. Michael Scott did both in "Fun Run," and ended up in the hospital as a result. He did earn Meredith's forgiveness though, so that's something.
Stanley Shouldn’t Have Yelled At Michael
"Did I Stutter?" is a line so iconic in The Office that it's the title of the episode. If only Stanley had remained calm and collected as he often is and not shouted at Michael during the meeting, he could’ve avoided a lot of headache trying to explain to his boss why he doesn’t respect him. It all ultimately worked out, but I doubt the crossword puzzle was finished during work hours that day.
Michael Shouldn’t Have Listened To His GPS
The unfortunate blunder in “Dunder Mifflin Infinity” is so on point with the rest of the episode, one can’t help but laugh. Only Michael Scott would set out to prove that being tech savvy isn’t the key to a flourishing business, only to be rejected by former clients complaining about their bad website. Michael then crashing a rental car into a lake because he was listening to his GPS is the perfect exclamation point that drives the joke home oh so perfectly.
Darryl Shouldn’t Have Listened To Kelly’s Subtext Texting Notes
Darryl deserves a reckoning for hitting on a woman in a committed relationship the same as Jim does Pam, though he was far less sneaky. Allowing Kelly to analyze the dots in the text in "After Hours" helped Val's boyfriend Brandon realize something was up, which made for some awkward moments between them.
Michael Sending The Picture Of Jan On Vacation
"Back From Vacation" featured an epic mistake by Michael Scott, though it could've gone a lot worse. While he did accidentally send the picture of him and Jan in Jamaica to everyone on the "packaging" mailing list, at least Jan didn't find out about it (at least, not until much later)! There are worse mistakes to make.
Gabe Makes A Romantic Scavenger Hunt For Erin... That She Does With Andy
Poor Gabe can never catch a break in The Office, so of course when he tried to woo Erin in "PDA" with a scavenger hunt, it blew up in his face. Erin, as innocent as she is, decided to enlist Andy to help even though they once dated. They end up having a great romantic time, which wasn't Gabe's intention.
David Wallace Putting Charles Miner Between Himself and Michael
Hiring Charles Miner, in general, wasn't a great move for David Wallace, but it really was a terrible mistake for how it impacted his relationship with Michael. With the lines of communication between them strained in "New Boss," Michael ultimately quit and began his own paper company proving he was good at his job which created big problems for David and Dunder Mifflin at large.
Charles Picking Dwight As The Number Two Of The Office
Dwight has consistently proven in The Office that he's not to be trusted with any measure of power. Of course, Charles wasn't aware of that and even went so far as to admonish Jim to David Wallace in his support of making Dwight "Number 2 of the office." It wasn't Charles' greatest misstep, but it did make him terribly unlikable.
Jim Dressing Up In A Tux On Charles' First Day
Jim learned the hard way in "New Boss" that his pranks on Dwight are something he could only get away with under Michael. Charles Miner arrived and immediately looked down on Jim's explanation that he wore a tuxedo to belittle a colleague's memo about appropriate company policy. It's probably one of Jim's most humbling moments in the series. Also, Idris Elba's performance as Charles in this solidifies it as one of his best roles.
Pam Messing With Buttons On The Elevator
In "Nepotism" the "Bart Simpson of Scranton" aka Pam decided to pull an epic prank on Dwight. After allowing Kevin to rig the elevator buttons to make them all go to different locations, she ended up stuck with him on the broken down elevator. Ultimately, Pam lost the prank because Dwight promptly urinated on the elevator floor while they waited for it to be fixed.
Dwight Standing On Coals
"Beach Games" contains the most painful error of the series, as Dwight stood on hot coals and refused to move off until Michael gave him the promotion. It ended with Dwight in a lot of pain, and without a promotion.
Kelly Running Off With Ryan
Kelly's biggest flaw in The Office was never being able to let go of Ryan, and this presumably continued even after the series ended. Kelly moved to Miami, Ohio, to be with her fiancé, and Ryan conveniently moved there as well. The two ultimately reconnected during the wedding in the finale, and ran off together. Why can't these two leave each other alone?
Toby Moving To Costa Rica
Toby decided to get a fresh start in Costa Rica, seemingly because he wasn't able to woo Pam. We later see him laid up in a hospital with a broken neck after a zip line accident in "Weight Loss," and he eventually came back to Scranton.
Meredith Parking Her Car In The Mall
Meredith offered to drive the women and Michael to the mall for "Women's Appreciation," and absolutely destroyed a few cars in the process. She didn't seem too concerned about it either, which may indicate this isn't the first time it happened.
Oscar Underestimated Angela’s Wrath
Oscar learned not to mess with Angela the hard way in "The Target" when she hired a guy to break his kneecaps for seducing the father of her child. Fortunately, the assailant wasn't successful, but yeah, don't mess with Angela.
Ryan Attempted To Ask Pam Out
Ryan was in rare form in "Dunder Mifflin Infinity" and even felt like he could ask Pam out. She declined, of course, as she was officially dating Jim. It ended pretty embarrassingly for Ryan, but what doesn't for him?
Stream The Office right now because it's one of the best shows to watch on Peacock. Of course, there's a lot of other quality content on there, so having a look around at what else is available certainly wouldn't be a bad choice.
