15 Most Awkward Michael Scott Moments

Wednesday, May 26 by

One of the reasons "the office" has remained so eminently watchable over the years is Steve Carell as the clueless Dunder-Mifflin boss Michael Scott. The actor, combined with a great script, just has a talent for wringing the most extremely painful awkwardness out of basically any situation. Making a list of the most awkward moments is like picking the most apple-y of apples. Awkwardness and Michael just go hand-in-hand – every single episode contains something that makes you cringe while laughing at how uncomfortable he can make people, but there are those memorable moments that stand out even amongst 115 episodes. And knowing that we only have one more season of Michael’s hi-jinks to look forward to, it seems appropriate at the end of this past season to take a look back at all the most excruciatingly embarrassing ways the actor has made us laugh. Whether NBC continues "The Office" after Carell’s departure or not remains to be seen, but one thing is for sure – nobody will ever be able to replace the lovably simple-minded boss who gave us….

The 15 Most Awkward Michael Scott Moments!

15.  “Happy Hour,” Episode 620
Date Mike
If there’s one thing Michael Scott has proven over the course of six seasons, it’s that he tends not to learn from his mistakes, and “Date Mike” is one of the best examples of this truism.  After dating Jan, Carol, and Holly and having at least semi-success with them by not being a complete idiot 100% of the time, he blows every single chance he has when he finds out that the girl he meets at a restaurant is actually someone Pam is trying to set him up with.  The second he finds out he goes into full-on ballistic awkward mode as he takes on a persona meant to be some kind of cool player-type, dancing on pool tables and generally making a fool of himself, destroying his chances like only Michael Scott can.

14.  “The Alliance,” Episode 104
Meredith’s Birthday Card
Even all the way back in Season 1, "The Office" writers had Michael’s awkwardness down pat, in one of the most memorable scenes of the whole series.  When Meredith’s birthday rolls around, Michael needs to come up with the perfect quip to write on her card, and he ends up reading out several, among them, “Hey Meredith, Liz Taylor called, she wants her age back and her divorces back!”  “Meredith, let’s hope the only downsizing that happens to you is that someone downsizes your age.” You can’t help but laugh and cringe as his increasing attempts at humor fail miserably and put a pall on the whole affair.

13.  “Diwali,”  Episode 306
Michael Proposes to Carol
A the office pointed out to him a few episodes before this past season’s finale, Michael tends to torpedo relationships he’s in through his own idiocy. Though this particular awkward incident didn’t finish off his relationship with Carol, it did make the list simply because of the mind-boggling balls it took to put himself out there in front of everyone at the Diwali celebration and ask a woman he’d barely been dating at all if she wanted to tie the knot.  It was the beginning of the end for Michael & Carol, and one of Michael’s most awkward moments ever.

12.  “Diversity Day,” Episode 102
Kelly Slaps Michael
If there’s one issue where Michael tends to show the most ignorance, aside from maybe women, it’s race.  Whether he’s talking about Stanley’s “urban” vibe or asking if Darryl used to be in a gang, he just can’t seem to get non-white people.  And before Kelly became the superficial bitch of the office, she got a full-on taste for Michael’s insensitivity when, in the name of the game they were playing, Michael talks to her in full-on Indian stereotype mode, which earns him a hard slap in the face.  As he turns to the office his response is priceless, “Now she knows what it’s like to be a minority!”

11.  “Pilot,” Episode 101
Michael Fake-Fires Pam
Poor Pam.  Though eventually the series turned her into pretty much the one character in the office who tended to have the most sympathy for Michael, this series-opening moment really set the bar high for how awkward things could get between the two of them.  (Not counting an upcoming item of the list.)  When Michael fake-fires her, bringing her to tears, and he tells her it’s a joke, adding that Ryan was in on it the whole time, the pan to the temp shaking his head disbelievingly is perfectly done and cringe-worthingly funny.

10.  “Company Picnic,” Episode 526
Slum Dunder-Mifflinaire
Office fans now that there’s really one woman for Michael Scott, and that is Holly Flax.  She has her own quirky personality that’s similar enough to Michael’s while being able to be the grown-up for the both of them.  Her ability to be co-awkward with Michael reached a climax when they gave a presentation to the five branches assembled at the company picnic, which included after an awful sketch parody of “Slumdog Millionaire."   Not only was the sketch classic Michael-Holly awkwardness, but the ending sealed the deal with the co-reveal of which branch was closing.

9.  “Sexual Harassment,” Episode 202
Pam’s New Girlfriend
As mentioned above, in the earlier seasons, Pam was often the butt of Michael’s awkwardness.  Women being one of the main things Michael just can’t seem to understand, she was always prime material for his blunders, and in this episode, he tries to get her to make out with a sex doll so that they can test out a hypothetical situation of her bringing her girlfriend into the office and making out with her.  The cutaway in this scene is one of the best of series – Michael’s simple gesture of grabbing the doll and saying, “Pam?” followed by her slack-jawed expression and an immediate cut to the sexual harassment training video leaves you gasping for air.

8.  “Niagara,” Episode 604
Michael’s Toast
If you want to be sure not to embarrass yourself, it’s best not to bring Michael with you to any kind of social event.  What possessed Jim and Pam to invite Michael to their wedding, we’ll never know (and let’s not even get into Phyllis’s wedding), and even though it ended up being Jim who let it slip that Pam was pregnant to their conservative grandmother, Michael did what he does best and rambled on for a good three or four minutes about how Jim and Pam are having lots of sex and are living together as well, each further second digging both him and his underlings into a cold dark hole with him.

7.  “Take Your Daughter to Work Day,” Episode 218
Young Michael
One of the reasons this episode is notable is because it gave us one of the first real glimpses into the depths of Michael Scott’s character, why he is the way he is today, a big departure from the British original.  He brings in a video of a children’s show he was on back in the day, and everyone stares in shocked silence as a ten-year old Michael explains to the camera that in the future that he wants to have a hundred kids so that nobody can ever say no to being his friend.  As the staff watches in shocked silence, we can’t help but think, while laughing in a horrified manner, “Damn, this guy has some issues!”

6.  “Lecture Circuit:  Part 2,” Episode 515
Michael’s Meltdown
Before this episode, we’d seen Michae break down before, and we’d seen him be awkward in front of a large group of people, but sometimes it works best when they’re people he doesn’t know, who are confronted head-on with his brazen awkwardness.  Once he finds out Holly’s new boyfriend is the salesman AJ, his presentation goes downhill from there, until he’s on his knees and slowly crawling out the room, breathing heavily.  Some have said this kind of scene destroys the office’s verisimilitude, but one thing you can’t argue – its hilarity and awkwardness.

5.  “Sexual Harassment,” Episode 202
Stanley’s Hot Catholic Schoolgirl
This episode, still today, easily stands tall as one of the best written and most awkward episodes of the whole series’ run.  Michael, as usual, just trying to make friends by smoothing things over and getting people to like him, assures Stanley that the hot Catholic schoolgirl he has posted on the wall next to his desk does not offend him, and that it is sexy and he loves walking by it every morning.  Dead silence reigns in the office once Stanley informs him that the girl is his daughter, and that picture won’t be staying up much longer.  The look on Michael’s face is horrified while simultaneously trying to cover up his mistake. 

4.  “Scott’s Tots,” Episode 611
Michael Scott’s Broken Promise
This particular episode was more cringe-worthy than outright funny, but the scene is just so unbearable it deserves a high place in this list.  We learn that Michael pledged to pay the college tuition of a fe high school kids if they graduated, but of course Michael doesn’t look to the future, and so graduation day has a arrived and Michael has to tell a school room full of eager kids that he can’t give them the money they need.  It’s one of those moments where you want to laugh and scream at the same time while uncomfortably writhing in your seat.

3.  “Business School,” Episode 316
Michael’s Presentation
Any time Michael is asked to go anywhere outside the office, he feels very important, like the big cheese, and even though Ryan only needed him for a Q&A for his business class, Michael ends up monopolizing the class meeting to instruct the economics students on the real practicalities of business, tossing candy bars into the class at random and ripping the pages out of a poor student’s notebook.  The random nonsensical advice he gives combined with the straight-faced, bewildered looks of the students make this both hilarious and almost unimaginably awkward.

2.  “Gay Witch Hunt” Episode 301
Michael Kisses Oscar
Okay, maybe I lied about race and women being the main two things that Michael doesn’t know anything about.  The other one is homosexuality, and this is put to the utmost test when he finds out that Oscar is gay.  Every interaction he has with his employees up to the actual moment is great, and as always – Michael on a mission to do some good is never a good idea, no matter how honest his motivations may be.  The kiss between him and Oscar was simultaneously revolting, disturbing, awkward, and funny (and also non-scripted), lasting only a couple of seconds, but seeming to last absolutely forever.  It’s something neither us nor Oscar will ever forget.

1.  “Dinner Party” Episode 409
The Whole Freaking Episode
No Awkward moment best exemplified what “The Office” is all about than "Dinner Party" – an episode that capitalized on awkward moments and great character development.  When Jim and Pam are finally tricked into attending Michael’s house for dinner, we expect awkwardness to ensue, but what we get are a slew of unbelievably painful scenes, ranging from Michael explaining the physical toll three vasectomies can have on a person, to asking Jim and Andy if they’ll invest in Jan’s candles, to the not-so-subtle passive-aggressive attitude between him and Jan the whole evening, while Pam and Jim sit there in stunned silence.  We got to see more about characters we loved, we got to experience some great awkward moments, and most important, we laughed our asses off while choking it back in horrified disbelief at the turns the plot kept taking. A great episode all around, and certainly the most awkward Michael Scott moment ever.

-THOMAS ANDERSON, aka MOVIEBUZZREVIEWDUDE. Check out his movie/media/pop culture blog HERE.

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