19 best Michael Scott moments from The Office that you simply can’t forget

When it comes to comedy, Steve Carell owns the screen with his epic portrayal of Michael Scott in the famous mockumentary sitcom The Office. With all his flaws and childlike enthusiasm, he is one of the most hilarious and wholesome characters in television history. He’s the “world’s best (read: most entertaining) boss,” who overexerts himself, flops magnificently, and yet remains oddly endearing. This walking comedy of errors has blessed us with countless iconic moments and episodes, still as meme-worthy and rewatchable as ever. Here are 19 of the best moments that make Michael Scott so unforgettable.

1) “That's what she said”

There’s no phrase more synonymous with Michael Scott than “That’s what she said.” This cheeky, double-meaning catchphrase became a signature line on The Office, with Michael dropping it at every available (and sometimes perfectly fitting) inappropriate occasion. Every time he's uttered these four hilarious words, laced with sexual innuendo, it’s been almost impossible not to laugh—despite the gravity of the situation or the compromise of professionalism. Some of the most memorable instances include when Jim said, "You always left me satisfied and smiling," or when Michael talks about a 'big box of things,' and several others.

2) When Toby returns (Season 5, Episode 9)

If Michael Scott despises anything more than logical reasoning, financial restrictions, and farewells, it’s Toby Flenderson. Right from season 1 of The Office, Michael’s outright and inexplicable dislike for Dunder Mifflin’s most harmless employee is as absurd as it is hysterical. One of the most iconic Michael-Toby moments unfolds when Michael, ecstatic over Toby’s departure, is suddenly devastated upon realizing his nightmare isn’t over; Toby is back. And his reaction is pure comedic gold. With a look of unfiltered dread, he shouts, "Nooo! God, no!" and recoils as though Toby’s mere presence is an apocalyptic event.

3) The Dundie Awards (Season 2, Episode 1)

The annual Dundie Awards, Michael Scott’s most beloved tradition, were his way of celebrating the office’s best (and worst) traits. Held at Chili’s, this low-budget, high-enthusiasm event saw Michael handing out trophies for ridiculous categories like 'Whitest Sneakers' and 'Hottest in the Office.' Even with the secondhand embarrassment, there’s something oddly touching about Michael’s unwavering mission to make his coworkers feel 'special' in the most ridiculous ways. His tone-deaf song parodies, painfully awkward speeches, and desperate attempt to turn the event into an Oscar-worthy night prove just how much he craves being the center of attention.

4) Michael is lost (Season 7, Episode 15)

One of the most iconic Michael moments happens in Season 7, Episode 15 when Jim leaves him stranded at a gas station with his phone and wallet locked in Jim's car. While his office employees try to track him down, Michael stumbles around Scranton in his usual clumsy way, stopping at a pet store to "talk" to the animals and even visiting a hot dog stand to trade his watch for food. But everything he does is driven by a deep longing for connection. The humor here isn’t just rooted in his cluelessness; it's a poignant reminder that beneath the title of “World’s Best Boss” is a man who frequently battles loneliness.

5) Michael hits Meredith with his car (Season 4, Episode 1)

In a classic case of Michael’s recklessness, he accidentally hits Meredith Palmer with his car in the office parking lot. The funniest part about this moment is how he's far more concerned about his parking spot than his employee's well-being. As if that wasn’t enough, Michael continues acting as though it’s all no big deal. It’s a chaotic mix of Michael’s delusion, absurdity, dark humor, and his unrelenting need to turn everything into his own version of ‘better,’ regardless of the cost to others.

6) Michael grills his foot (Season 2, Episode 12)

One of Michael Scott's most comically unintentional moments in The Office is when he quite literally grills himself. As he explains, he enjoys waking up to the aroma of bacon, so he keeps a grill next to his bed. But one morning, he accidentally steps on it, badly burning his foot. Michael then turns his minor injury into an office-wide spectacle, limping throughout the day and ensuring that his coworkers acknowledge his suffering. This fiasco is the peak Michael Scott moment, a breakfast-in-bed gone terribly wrong, that never stops being funny no matter how many times you rewatch it.

7) Michael at Pam’s art show (Season 3, Episode 16)

Michael Scott can be many things, from an inappropriate boss to a walking disaster. But every now and then, he does something so heartfelt that it almost makes you overlook the chaos he causes. While others are either too busy or critical of Pam's paintings, Michael not only shows up at the art show but also uplifts her with genuine praise. He's surprised to see that Pam has displayed a painting of their office building. Without hesitation, he insists on buying it, not out of pity, but because he genuinely loves it. After a long day where no one appreciates her work, Pam is truly overwhelmed by his kindness. It remains one of Michael's best moments in The Office.

8) Prison Mike (Season 3, Episode 9)

With a purple bandana on his head and an exaggerated, gruff accent, Michael Scott’s 'Prison Mike' stands as one of the most legendary moments. This happens when the office finds out that they’ve hired Martin, a former convict, and Michael, unsurprisingly, is determined to demonstrate what life in prison is like. He rambles on about how tough prison life is and claims that Dementors (from Harry Potter) are the worst part. His delusional thoughts, bizarre beliefs, and fictional stories are, frankly, pretty entertaining. These elements turn the moment into a comedy masterpiece.

9) Michael declares bankruptcy (Season 4, Episode 8)

Michael Scott’s complete lack of self-awareness is best illustrated when he confidently announces his bankruptcy. As Michael finds himself in the midst of a financial crisis, he misinterprets Oscar’s advice and after a pointless conversation with Creed, he makes an even bigger fool of himself. In a theatrical burst, Michael stands defiantly in the middle of the office and dramatically yells, 'I declare bankruptcy!' It’s not just the absurdity of the situation that makes it funny—it’s the fact that Michael genuinely believes this dramatic proclamation will solve his financial troubles.

10) Michael on the roof (Season 3, Episode 20)

Michael Scott thrives on attention, but even more so on making a dramatic point. In the Safety Training episode, he takes that obsession to ridiculous new heights (quite literally). After Darryl calls him out for having it easy in the office compared to the warehouse staff, Michael decides to prove the difficulty of his job by dramatically faking a suicide attempt. Obviously, the best way to respond to a minor workplace inconvenience is to climb onto the roof and stage a scene. This scene was so hilariously exaggerated, yet we can’t help but adore him.

11) The speech that goes nowhere (Season 5, Episode 12)

Michael Scott has countless unforgettable moments in The Office, but one of the most hilariously awkward scenes is his attempt to impress David Wallace with an insightful speech, only to leave him utterly confused. Called to Wallace's office because Scranton had the highest sales numbers under his management, Michael is excited to share his vast knowledge. He starts with boundless enthusiasm, determined to make an impact, but his speech goes absolutely nowhere. Meanwhile, David sits motionless, his expression growing increasingly bewildered, silently wondering why he asked in the first place.

12) The disastrous dinner party (Season 4, Episode 13)

Michael’s dinner party with Jan is undoubtedly one of the most unforgettable moments in The Office history. Throughout the evening, Michael does his best to maintain a light-hearted and charming atmosphere, desperately hoping his eccentric attempts at hospitality will win over the uninvited guests. Meanwhile, Jan’s sarcastic remarks and hidden barbs expose the toxic dynamics of their relationship. Then, there’s that legendary moment when, after an awkward string of exchanges and wine pairings that left everyone questioning their choices, Jan flings one of Michael’s treasured Dundie Awards at his plasma TV. The episode is a humor-packed treasure.

13) Michael roasting everyone (Season 5, Episode 15)

Michael Scott roasting everyone is one of those peak moments from The Office that make it impossible for fans to watch without cracking up. Humiliated and battered by a brutal office roast, Michael returns with razor-sharp comebacks. He fires off a series of zingers like, “Jim, you’re 6’11” and you weigh 90 pounds. Gumby’s got a better body than you—boom, roasted!" It’s these raw, unfiltered moments that keep Michael Scott etched in our memories.

14) A father figure to Erin

Michael Scott may have had his fair share of awkward moments, but he also had a pure heart, and that was nowhere more evident than in his relationship with Erin. Erin, the perpetually cheerful yet slightly naive receptionist, spent her childhood in foster care, never knowing the comfort of a stable parental figure. Ironically, Michael stepped up and somehow became the closest thing she had to a father. Their father-daughter dynamic shone through the small, heartwarming moments, like when he calms Erin after she's feeling insecure about Andy's past with Angela, or when Erin desperately wanted Michael to like Gabe when they started dating.

15) Michael's proposal to Holly (Season 7, Episode 19)

Michael’s proposal to Holly is undoubtedly one of the sweetest and most memorable moments in The Office. His efforts at love usually come off as awkward, clumsy, and a bit absurd. But with Holly, it’s a different story. He plans a grand proposal for her in the office, with candles everywhere, only for it to be hilariously interrupted by the fire sprinklers. Despite being drenched in water, the moment remains perfect, and when Holly finally says yes, it is nothing short of spectacular.

16) The Michael Scott Paper Company (Season 5, Episode 25)

Michael thrived as the boss, so when Dunder Mifflin’s new VP, Charles Miner, kept him under constant supervision, he did the only logical thing: he quit and started his own damn paper company (Michael Scott Paper Company). With no money, no office, and no real plan, he relied solely on confidence and an unshakable belief in his genius. Recruiting Pam and Ryan, who were just as lost, he set up operations in a tiny, bleak office. The best part is that it actually worked out. They started poaching Dunder Mifflin’s clients, forcing David Wallace to buy them out. And just like that, Michael secured his old job back, with a raise.

17) Michael's farewell (Season 7, Episode 22)

Michael’s departure from The Office marked the end of an era. He entertained us for seven seasons, so when he finally said his goodbyes, it felt like a punch in the gut. At his last Dundies, his colleagues even sang "9,986,000 Minutes," as a tribute to the exact time Michael spent at Dunder Mifflin. What made Michael's farewell even more special was how quietly he left. No grand gestures, no dramatic goodbyes, just individual moments with each coworker, never revealing it was his last day. It was ironic for someone who loved big moments to dread his own departure.

18) Dwight's recommendation letter (Season 7, Episode 22)

Watching Michael Scott, the self-proclaimed but pretty legendary “World’s Best Boss,” say goodbye to The Office was nothing short of an emotional whirlwind. But if one scene shattered our hearts beyond repair, it was his heartfelt recommendation letter for Dwight. Even though Michael isn’t there in the room when Dwight reads it, his influence is palpable in every word, reminding us that the impact of his character goes far beyond physical presence. He declares that Dwight as a sales executive, leader, man, and friend "is of the highest kind, quality, and order, supreme."

19) Dwight’s wedding (Season 9, Episode 23)

Michael's exit from The Office left a significant gap, making his sudden reappearance at Dwight and Angela's wedding in the series finale all the more heart-wrenching. Michael's return is a full-circle moment. Dwight had always looked up to Michael, and it only made sense for him to stand by his side on the most important day of his life. Michael, stepping in as Dwight’s best man, delivers his iconic line: “That’s what she said,” and it’s the moment fans had been eagerly anticipating. There's a heartwarming, nostalgic quality to this moment, reminding us that, for all his eccentricities, Michael Scott will always remain the heart of The Office.