When it comes to fictional television bosses, there are none who make us shake our heads in disbelief, recoil in embarrassment, and laugh hysterically (often all in the same scene) more than The Office's Michael Scott. Played by Steve Carell for 7 seasons, Michael's actions run the gamut from unbelievingly tone-deaf to completely socially ignorant. He kissed his co-workers, forced them into uncomfortable situations, and wasn't shy about infusing the workplace with more than a few sexual innuendos.

All of this makes us wonder how he rose to be the regional manager of a paper company in corporate America. But like the true identity of the Scranton Strangler, some things are a mystery. What is clear, though, is the sheer amount of Michael's cringe-worthy scenes throughout his seven seasons. From insulting his employees, to propagating racial stereotypes, and every other wince-inducing moment in between, here are the top 9 cringiest Michael Scott moments that will make you shake your head in horror and disbelief.

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9. Hitting Meredith Wit His Car ("Fun Run")

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Sometimes Michael brings danger to his employees. Other times, he is the danger.

What begins as a routine morning soon turns disastrous. Distracted by telling the documentary crew about his floundering (and toxic) relationship with Jan on the way to work, he takes his eyes off the road as he's pulling into the Dunder Mifflin parking lot...and hits Meredith (Kate Flannery) with his car. It's one of the show's most gasp-worthy moments that makes us want to simultaneously cover our wide eyes at Michael's carelessness and laugh hysterically while we're doing it.

But while other members of the office might offer an apology and a bowl of Kevin's famous chili for sending Meredith to the hospital with a broken pelvis, Michael takes it a step further. When he learns that she was given a precautionary rabies shot due to some unrelated animal bites, Michael naturally takes credit for saving her from rabies (that she doesn't have) since it was his fault she was taken to the hospital in the first place. Only someone as airheaded and self-centered as Michael Scott could turn the horror of hitting someone with his car into an undeserved moment of self-congratulation.

8. His Inappropriate "Dundie" Awards ("The Dundies")

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In other workplaces, handing out awards to employees for jobs well done would be a morale booster. But at Dunder Mifflin, Michael turns something with the potential to be positive into something beyond inappropriate and cringe-worthy.

Michael forces the office to his annual presentation of "The Dundies," an award show that he created to bestow trophies for jobs well done (but mostly insulting superlatives) upon his staff. Notorious stick-in-the-mud Angela (Angela Kinsey) is awarded the "Tight-Ass Award," while Kelly (Mindy Kaling), who is Indian, receives the "Spicy Curry Award." What's even more gasp-worthy than the offensive superlatives is that Michael genuinely thinks these are funny (and appropriate for the workplace!). The rest of the office shakes their heads and cringe at Michael's behavior but Michael seems to think that there's nothing wrong with a little name-calling and casual racism.

The Dundies make another appearance in "Michael's Last Dundies" (Season 7, Episode 21), and the awards are no kinder. The overweight Stanley (Leslie David Baker) is awarded the "Diabetes Award," Toby wins the "Extreme Repulsiveness Award," while Oscar (Oscar Nunez) is given the title of "Worst Salesman of the Year." Despite the five-season gap between both Dundies episodes, Michael's social filter doesn't seem to grow much. His insults and racial slurs continue when he awards Angela the "Kind of A Bitch Award" and offers Darryl (Craig Robinson), who is black, the incredibly offensive "Moving On Up Award" in reference to the theme song to The Jeffersons.

7. Planting "Marijuana" in Toby's Desk ("Frame Toby")

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Michael's outright hatred for soft-spoken HR representative Toby (Paul Lieberstein) is a recurring plot point throughout the series, but this moment takes the cake. When Michael learns that Toby is returning to Dunder Mifflin, he makes it his personal mission to get rid of him once and for all. He tries to get Dunder Mifflin's Chief Financial Officer to fire him, attempts to frame him for sexual harassment, and even tries to provoke Toby into punching him. All of these plans fail and Michael is left with one last option: planting drugs in his desk. "It seems awfully mean," he says to Dwight (Rainn Wilson), "but sometimes the end justifies the mean."

Michael buys $500 worth of what he's told is marijuana, plants it in Toby's desk, and calls the cops. When they arrive and hold up the bag that Michael planted, they are quick to point out that it's actually a bag of Caprese salad. "Some basil...salad dressing, I think," one of them says.

6. Forcing Meredith Into Rehab ("Moroccan Christmas")

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After hitting someone with their car and claiming it was a positive thing, most people would quit while they're ahead. Michael Scott is not one of those people.

When Meredith's hair catches fire after she has a little too much to drink at the office Christmas party, Michael believes it to be his mission to get her the help he believes she needs. First, he tries to convince her that she's an alcoholic (which she denies). Then he tries to get her to see the error of her ways with a disastrous intervention that crosses way over the line of acceptable office behavior — and HIPAA privacy rules. "Okay, you know what I thought we should do is have a quick intervention and then get back to the party," he says in a cringe-inducing scene where he gets his staff to take a vote on whether or not they think Meredith has a drinking problem. When both attempts fail, he coerces Meredith into his car by telling her he's taking her to a bar. The only problem? They're not going to bar. Instead, Michael pulls up to the entrance of a rehab facility. When Meredith refuses to go inside, Michael responds by grabbing her and forces her into the center by literally dragging her through the front door.

Upping the cringe factor is Michael realizing that "you can’t just check someone into rehab against their will. They have to do it voluntarily. They have to hit rock bottom." But does Michael find a new way to truly help Meredith? Nope, he sure doesn't. Because he already knows what he needs to do: "I need to find ways to push Meredith to the bottom."

5. The Blind Date with Pam's Landlady ("Chair Model")

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Moment of Cringe #1: Michael's audible disgusted "Ugh" at seeing Margaret's face. Oof.

Moment of Cringe #2: Pretending that he's not Michael Scott when Margaret introduces herself. "Is who a Michael what?" he says. "Oh, that’s not, yeah I’m not..." Yikes.

Moment of Cringe #3: When the barista at the coffee shop they're in announces a drink order ready for Michael. "Michael? Michael?" the barista says, reading his name on the cup. "Large hot chocolate with caramel and a shot of peppermint." Ouch.

There's no walking back from that. At the end of the Crescendo of Cringe, Michael's focus on vanity, as well as his lies, have been exposed...along with his awful taste in warm beverages.

4. Fake Firing Pam ("Pilot) and Erin ("Casual Friday")

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If there's one way to ensure happy and productive employees, it's to pretend to fire them. Or at least that must be what Michael thinks since he does it so often throughout the series. The first time is in the show's premiere episode when he calls Pam (Jenna Fischer) into his office to fire her for "theft...and stealing" of Post-it notes. Pam's crying during this moment drives home Michael's cruelty and lack of social awareness even when he reveals that Pam wasn't really being fired. "Surprise!" he says. "It's a joke! We were jokin' around!"

It's the same "prank" he pulls with Erin (Ellie Kemper). "This is very difficult to say..." he says, "but no one here likes you in the office and we are going to have to let you go." Her wide eyes and open mouth show her shock while Michael bursts into laughter as if he has just played the most innovative and hilarious joke of all time. While Erin eventually finds the humor in it, Pam is much more critical. "You're a jerk!" she says, and it's hard not to agree with her. After all, who would take pleasure in snatching away someone's livelihood and sense of purpose?

Oh, that's right. Michael Scott.

3. Demonstrating the Dangers of Depression ("Safety Training")

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Rather than bringing in a professional to speak to the office about mental health awareness, Michael takes it upon himself to put on his own demonstration...and it's as disastrous and cringe-worthy as it sounds. Michael stands at the edge of Dunder Mifflin's roof and pretends he's going to jump. "My life!" he wails. "Oh, my life! The stress of my modern office has caused me to go into a depression!" His employees stand below, unsurprised at their boss's antics. "My head is in such pain and turmoil...and that is why I am going to jump off this roof!" Michael's performance is so on-the-nose that it makes us embarrassed by proxy. Combined with his cheesy, rehearsed dialogue and lack of sensitivity surrounding mental health, it's clear that Michael has no real clue about the dangers of depression. But that doesn't stop him from trying to impart his "wisdom" on his employees...and nearly killing himself in the process.

2. Just About All of Diversity Day ("Diversity Day")

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After Michael continues to (offensively) imitate Chris Rock, Dunder Mifflin sends someone from corporate to conduct diversity training at the office. Naturally, Michael finds it to be a waste of time and instead decides to hold his own diversity training. But what Michael considers training and what the professionals consider training are two very different things. This is hugely evident when Michael forces everyone to tape an index card to their forehead featuring the name of a prominent historical figure ("Martin Luther King Jr.") or nationality ("Asian," "Jewish," "Jamaican") and then makes them give "clues" (re: offensive stereotypes) to each other about their card to help them guess what it says. Disaster (and racial insensitivity) ensues in one of the show's most peek-through-your-fingers-because-this-is-so-awkward moments.

"Diversity Day" rachets up viewer discomfort to incredibly high levels. We experience shock, embarrassment, and more than a few cringe-worthy moments over the course of a single episode, and Michael's "training" activity only serves to highlight his own stereotypes and insensitivities. But before the episode ends, Michael leaves us with one final example of his wince-worthy aloofness: "You'll notice I didn't have anybody be an Arab. I thought that would be too explosive. No pun intended."

1. Scott's Tots ("Scott's Tots")

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Even 12 years after it aired, the "Scott's Tots" incident is hands-down the most cringe-worthy Michael Scott moment of all time. The premise is hugely embarrassing and hands-over-your-mouth gasp-inducing even by Michael Scott standards. Years ago, Michael set up the "Michael Scott Foundation" and promised a group of third graders that he would pay for their college tuition if they finished high school. Now, ten years later, Michael has to pay up. The only problem? He knows he doesn't have the hundreds of thousands of dollars to do so and has to break the news to the now high school seniors. "I have made some empty promises in my life," he says to his aghast employees, "but hands down that was the most generous."

The cringe factor is upped when Michael goes to the high school to come clean. All the kids are wearing matching "Scott's Tots" t-shirts, chant his name when he enters the classroom, and even perform a song-and-dance routine ("Hey, Mr. Scott, whatcha gonna do? Whatcha gonna do? Make our dreams come true!"). It's all so hugely embarrassing that we have to remind ourselves that none of this is real.

As if that's not enough, Michael is presented with a classroom named after him ("The Michael Gary Scott Reading Room") while the kids take turns giving emotional speeches about how Michael's generosity inspired them to dream bigger and be their best selves. And when he finally does come clean about his lie, he gives the kids the next best thing to free tuition: not a laptop, but a laptop battery. "Hold on...they're lithium!" he says to the kids' protestations as if that matters.

The whole Scott's Tots debacle is eight solid minutes of mounting cringe-worthy moments, dialogue, and facial expressions that takes the awfulness of Michael Scott to new heights. Even though he does own up to his lie (and apologizes for it), the boldness of his empty promise and the amount of time (ten years!) that he allowed kids to think he was their guardian angel is mortifying.

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