Michael Scott Moments That Made Us Cringe

Who is Michael Scott? Well, he's the regional manager of a Pennsylvania paper company, an aspiring screenwriter, ice skater extraordinaire, and one of the most memorable characters in television history. He's also a horrible human being. Sure, Michael might think he's the world's best boss and a suave ladies' man, but really, he's racist, sexist, and super selfish. And for every moment where Michael does something nice for one of his employees, there are about ten where he's awful and incredibly cringey. Thanks to the hilarious Steve Carell and his brilliant comedic abilities, Michael is the kind of guy who embarrasses everyone around him, including people watching at home. While The Office is one of the funniest shows ever made, Michael's awkward antics constantly make us scream at the TV, "No! Don't! Stop!" From childish jokes to straight-up ruining lives, these are the Michael Scott moments that made us cringe.

In season five, Michael Scott meets his greatest enemy (well, other than Toby). Played by Idris Elba, Charles Miner is a hard-nosed businessman who's got no time for Michael's buffoonery. Worse still, he's just been hired as the new Dunder Mifflin vice president of northeast sales, so the moment he shows up at the office, Charles and Michael start butting heads.

Sure, the women of the office are absolutely taken with the guy, but Michael is trying his best to usurp and outshine his new boss, especially after Charles cut the budget for all office parties...including Michael's birthday. Their explosive power dynamic boils over into cringeworthy awfulness when Kevin asks Michael if he can work overtime. When Charles vetoes Michael's decision, the regional manager decides it's time for childish comedy routines and repeats every single thing that Charles says.

It's like Michael has suddenly turned into a five-year-old copycat, and Charles is getting angrier and angrier by the second. Things are getting so unbearable that the entire office—including Dwight and Andy, no strangers to embarrassing themselves—are shouting at Michael to stop. And yeah, we're shouting right along with them, desperately hoping that Michael will just shut up.

Until settling down with Holly Flax, Michael Scott's love life involved a series of destructive and disastrous relationships, like the time he broke every rule of workplace decorum by dating Helene Beesly, Pam's mom. After meeting at Jim and Pam's wedding, Michael and Helene hit it right off, much to Pam's perfectly understandable horror. It gets even worse when Michael won't stop talking about how, uh, compatible he is with Helene. The situation continues to escalate until Jim and Pam are forced on a double date with Michael and Helene, but when Pam sees how happy her mom is with Michael, she warms up to the idea that her boss might one day be part of the family.

Unfortunately, this birthday party is full of twists and turns, and while giving Helene a series of elaborate gifts, Michael realizes his girlfriend is quite a bit older than he is. Suddenly, he's looking for a way out of the relationship...right there...in a restaurant...on her birthday. Jim and Pam watch on, mortified and shocked, as Michael lists all the reasons he should split up with Helene: he wants to have kids, visit Italy, and skydive, all stuff he probably should've discussed before professing his undying love. The whole date is incredibly painful to watch, but at least Michael gets his comeuppance when Pam slaps him across the face.

Fact—Michael Scott is horrible with women. Second fact—Michael Scott is culturally insensitive. So when he brings his date, Carol Stills, to Kelly Kapoor's Diwali celebration, there's bound to be all sorts of trouble. For example, in Michael's mind, Diwali is just Hindu Halloween, so he tells Carol to come wearing a costume. And when the duo arrive at the party, poor Carol is dressed up like a cheerleader.

Yeah, that's pretty bad, but the real "please, Michael, no" moment comes after our bumbling hero talks to a happily married Indian couple. Inspired by their wedded bliss, he grabs a microphone and makes a grand announcement in front of a gym full of partygoers. Spilling his heart out, Michael pops the question to Cheerleader Carol right then and there. Yeah, this definitely isn't the place for this, and it certainly isn't the time, as this is only their ninth date. Humiliated, Carol shoots down his offer and runs off into the crowd. It's embarrassing for everyone watching, and it only gets worse when a dejected Michael tries to kiss Pam. It just goes to show that even during the festival of lights, Michael can't help being impossibly dim.

Michael Scott and Ryan Howard have always had a weird relationship. Michael wants to be Ryan's mentor, his best friend, and occasionally, his lover. Unfortunately, this friendship/obsession only goes one way, and Ryan often uses this to manipulate his boss. Case in point, the season three episode where Ryan—hoping to get a good grade—brings Michael to his business school so he can do a Q&A.

Michael can't wait to impart his "wisdom" to the next generation. Sadly, it's all a set-up. Ryan has no respect for his manager or the paper business, and he knows the class will eat Michael alive. Of course, Michael does a pretty good job of sabotaging himself, by walking into the classroom accompanied by his own theme song. Plus, Michael is a big believer in visual aids, and one of his teaching methods involves hitting a student in the head with a candy bar. The most awkward moment comes when Michael explains the basics of business to these MBA students, lecturing that, "The more stickers you sell, the more profit—fancy word for 'money'—you have to buy PlayStations and Beanie Babies."  

But once the students start asking questions, it becomes painfully obvious that Michael is in way over his head. The final twist of the cringey knife comes when he discovers that Ryan has betrayed him. It's a humiliating experience, but at least Michael gets the last laugh by forcing Ryan to work alongside his least favorite person in the office: his own girlfriend.

Michael Scott thinks he's a natural born leader, but he's also incredibly insecure. So whenever an authority figure suddenly shows up, Michael gets super competitive. That's definitely the case in the season two episode where Michael takes his employees on a booze cruise. Even before the ship sets sail, Michael refuses to admit a rather basic fact: the captain of the boat outranks the manager of the office.

In fairness, Captain Jack (played by Rob Riggle) is a bit of a jerk himself, but hey, it's his ship. And whenever Jack tries to make an announcement or get a party game going, there's Michael, stealing the mic and trying to spark a one-man mutiny. But things get really bad when Jack kicks off the dance contest as Michael is giving a speech on leadership skills. Ever the master of improv, Michael decides to go with the flow by taking over the dance floor and giving everyone a motivational dance lesson.

With everybody staring in abject horror, Michael pulls out all the moves. He skips and shakes, he's high-stepping and knee-slapping. He even throws in the worm for good measure. Phyllis is so ashamed that she looks away, as other spectators bite their lips to keep from laughing. But Michael is completely oblivious. As far as he's concerned, he's the real captain of the ship, the best regional manager, and the king of the dance floor.

Give Michael Scott a microphone, and you're guaranteed to regret it. That's a lesson we all learned the hard way in the first episode of season two, when Michael hosts the Dundies at a Chili's. An annual awards show of Michael's own making, the Dundies Show is supposed to reward the office employees for their hard work. Instead, it's an opportunity for Michael to make everyone squirm in their seats.

It all starts with a horrible hip-hop number, complete with cue card mishaps and tech issues. Things get racist when Michael hands Kelly the "Spicy Curry" award and assumes the white woman with Stanley isn't his wife. Both Phyllis and Angela win trophies that highlight parts of the body best left unmentioned at work events, and Ryan realizes Michael's true feelings when he's gifted the "Hottest in the Office" award.

And since Michael isn't exactly the most PC guy on the planet, we're soon introduced to Ping, Michael's Asian character who makes Mickey Rooney from Breakfast at Tiffany's look woke in comparison. He's got fake buck teeth, slanty-eyed glasses, and a truly offensive horrible accent. Pam describes the horror of the Dundies the best when she compares it to a car crash, one that's so bad you've got to stare at it...because your boss is making you.

In Michael Scott's defense, he isn't always a bad guy. Oftentimes, he means well, and in certain rare moments, he can be a chill dude. For example, he's on his best behavior in the season six episode when the office is hanging out during happy hour. In fact, when he meets Pam's friend, Julie, he actually treats her like a real human being. He's funny, polite, and charming, and the two really hit it off...until Michael learns that Pam brought Julie along in hopes of setting them up.

Once Michael realizes this is a date, that's when he morphs into one of his most obnoxious characters: Date Mike ("nice to meet me"). Wearing a backwards Kangol cap and armed with tips from reality TV, Date Mike struts around the bar with his chest hair exposed, tries tying a cherry stem with his tongue (only to choke on it), and spins his pool cue around like he's some sort of slick hustler, a move that majorly backfires when he sends drinks flying across the room. 

The worst part comes when Date Mike climbs up on the pool table and starts dancing his way across the felt. He even picks a fight with the bar owner before a bouncer shows up. Once Date Mike is distracted, Julie heads for the hills, unimpressed by Michael's chauvinistic "charm." From the moment that hat comes on to the moment he's playing his pool cue like an electric guitar, we're all desperately hoping that Date Mike would just disappear.

Christmastime is always interesting around the Scranton office. Sometimes there's a civil war brewing in the Party Planning Committee, and occasionally a drunken Meredith will set herself on fire. It's hard to get through the holidays without some sort of hilarious drama, but during season three, things are especially sad for Michael Scott. He's just broken up with his girlfriend Carol—cutting her ex-husband's face out of a family photo and inserting his own smiling mug probably wasn't a good idea—so he decides to rebound at the hottest spot in town: Benihana, or as he calls it, "Asian Hooters."  

Accompanied by his entourage (Andy, Dwight, and a reluctant Jim), Michael lets loose at the restaurant, and both he and Andy manage to pick up two waitresses. A few scenes later, the duo return to the office Christmas party with their dates, but after getting distracted for just a second, Michael confuses the two Asian women and can't remember which one is his date. 

After he finally figures out which waitress he brought to the party, we're treated to one of the most hysterical and humiliating Michael Scott moments. He brings his date in for a big hug and then surreptitiously marks her arm with a magic marker. That way, he won't get them confused again. It's a new low for Michael Scott, but as always, the regional manager has an unacceptable excuse. As the man himself put its, "All waitresses look alike."

It's a normal day at Dunder Mifflin until Michael Scott lobs a homophobic slur at Oscar. Obviously, that's never appropriate, no matter the circumstances, but in fairness, this is the beginning of season three, and Michael has no idea the accountant is actually gay. So when Michael is asked to apologize and tone down the insensitive behavior, well, things get a whole lot worse.

In a desperate attempt to make amends, Michael outs Oscar to the entire office and then forces everyone into the conference room where he gives a well-meaning but totally offensive lecture about being gay. He goes so far as to say that if he were gay, he'd be leading a pride parade, covered in feathers and waving a rainbow flag. Yeah, at this point, Oscar is burying his head in his hands, and honestly, so are we.

Just when you think it can't get any more awkward, that's when Michael tries to patch things up with a hug. Only when he wraps his arms around Oscar, Michael plants a kiss right on Oscar's lips. The accountant tries his best to escape, but Michael slowly gets closer until their lips are locked, and Oscar is traumatized for life. What makes this scene even funnier is that the lip kiss was improvised by Steve Carell, and actor Oscar Nunez had no idea it was coming until it was too late.

For all his many flaws, Michael Scott somehow runs the most successful office in Dunder Mifflin. So when the Stamford branch shuts down, six employees are ushered over to Scranton. But thanks to Michael's, uh, unique personality (and a whole lot of office drama), the folks from Stamford abandon ship at a staggering speed, and the first to go is poor Tony.

We don't know Tony all that well before he flees, but he seems like a perfectly nice dude. However, when it comes to the weight department, Tony makes Kevin look like an Olympic athlete. And while that's totally fine, Michael is obviously going to make Tony's weight into a big issue. Hoping to welcome the new employees, Michael encourages them all to climb on top of a table so they can be admired by everyone else. Of course, Tony is too heavy to get up there, but despite pleading with Michael to skip this ridiculous ritual, the boss insists, telling Tony, "Use the momentum of your lower half to hoist yourself up."

Obviously, Tony is frustrated and humiliated, but things reach unbearable levels when Michael and Dwight grab Tony's legs and try to shove the big guy on top of the table. It's all too much, and Tony quits right then and there, telling Michael his "management style" isn't so great. Needless to say, Michael doesn't take this well and fires his new employee, which proves the world's best boss isn't so good at handling weighty issues.

Michael Scott always has to be the center of attention—even at Phyllis' wedding. The bride-to-be asks Michael to push her father down in the aisle in a wheelchair, but about halfway to the altar, the old guy decides to get up and walk. It's a miraculous moment, and while everyone in the church is elated, Michael is left in the lurch...and seething with anger.

"Me walking Phyllis down the aisle was supposed to be the highlight of the wedding," Michael angrily tells the cameraman. Ever the immature child, Michael throws a tantrum by noisily dragging the wheelchair down the aisle. He then squeezes himself between the groomsmen, determined to be part of the ceremony. And that's when Michael starts calculating how he can steal the show. Right after Phyllis says "I do," Michael jumps out and loudly announces the two as a couple. Of course, Bob hasn't said "I do" yet, and Michael is forced to slink back in line.

Then during the wedding speeches, Michael steals the mic and gives an impromptu (and unwelcome) wedding speech, complete with quotes from The Princess Bride, celebrity couple names, and off-color jokes about poor Phyllis. Sure, Michael accidentally redeems himself before the night is over, but all these years later, this is still the cringiest wedding in TV history.

Let's give Michael Scott some credit for the nice things he's done. He was a father figure to Erin. He played paintball with Dwight. He showed up at Pam's art show and bought one of her paintings. But all of these wonderful things are canceled out by what happened in the show's sixth season, during The Office's most painfully cringey episode: "Scott's Tots."

Years ago, Michael Scott fell in love with a group of low-income elementary students. Figuring he'd be a millionaire by the time the kids were ready to graduate, Michael promised he'd pay their college tuition. But when it comes time to shell out, Michael is still just a middling regional manager who once tried to hop on a train because his finances are so bad. So when he's forced to visit the school to meet the now-grown-up kids known as "Scott's Tots," the tension is absolutely unbearable. Martyrs? A Serbian Film? Irréversible? They're all way easier to watch than what happens next.

When Michael shows up at the school, the kids absolutely adore him. They give speeches thanking him for changing their lives, and they even put on a song-and-dance number to show him their gratitude. By the time they're done performing, a guilty and terrified Michael gets up in front of the class, and reveals he can't pay for anything. But hey, he did buy them all laptop batteries to make up for his blunder. Needless to say, this does not go over well. Michael Scott might have good intentions, but the size of his heart doesn't match the size of his brain.