In the first season of The Office, Michael Scott was a vaguely Americanized mirror of David Brent, and it didn’t seem like we would ever root for him because the differences between Ricky Gervais and Steve Carell as performers meant that Michael didn’t work as a character. Over the years, the writers gave Carell more freedom to form Michael’s personality.
They gave him both moments of joy and of personal anguish. In the former, we’re glad to see him win, and in the latter, we’re heartbroken to see him upset, because Carell really humanized the character. Here are Michael’s five highest and five lowest points from the show’s nine-season run.
LOWEST: LEAVING DUNDER MIFFLIN FOR GOOD
In the extended episode “Goodbye, Michael,” Michael bids his employees farewell and prepares to move to Colorado to marry Holly. He tells everyone that his second-to-last day is actually his last day to avoid difficult goodbyes (which gives him a t-shirt idea: “Goodbyes Stink”). He’s excited to marry Holly and start a family with her, but he’s also melancholic about leaving Dunder Mifflin.
His goodbyes with everyone stand among the series’ saddest, sweetest moments, including Dwight, who he wins over with a game of paintball; Jim, who figures out the ruse and has a heartfelt moment where he declares Michael a great boss; and Pam, who rushes down to the airport to see Michael off when she misses him at the office.
HIGHEST: ATTENDING DWIGHT’S WEDDING
Michael Scott’s surprise return was, without a doubt, the greatest moment in The Office’s series finale episode. After he showed up to be Dwight’s best man and spoke to Pam at the reception, we learned that he’d married Holly and they’d had a couple of kids.
He was so proud of his kids that he took so many photos of them that he had to buy a second phone and get on a whole new cell phone plan.
LOWEST: FINDING OUT HOLLY HAS A NEW BOYFRIEND
In the two-part “Lecture Circuit” episode, Michael takes the secrets of his success on tour with Pam. Initially, they plan to avoid the Nashua branch, where Holly was transferred, leading to their breakup. But Michael decides to go to Nashua in search of closure. He really thought his connection with Holly was special, and that she was his soulmate — or “soup snake.”
Unfortunately, when he gets to Nashua, he finds that Holly is out of town and that she has a new boyfriend named A.J., Michael breaks down in the middle of his presentation as he asks A.J. about his relationship with Holly: “Does she ever talk about me?”
HIGHEST: PAM TELLING HIM THE CONTENTS OF HOLLY’S LETTER
After looking through Holly’s empty desk, Michael finds a file on her computer called “Dear Michael.” Against his better judgment, he copies the file onto his own flash drive and tells Pam about it.
Pam tells Michael he can’t violate Holly’s trust by reading it, but she offers to read it once for him, delete it, and tell him about its contents. What Pam finds is that Holly still has feelings for Michael, and their love story isn’t over yet. Michael’s sigh of relief is heartwarming.
LOWEST: TRYING TO RUN AWAY FROM HIS MONEY PROBLEMS
In the episode “Money,” Jan’s reckless spending of Michael’s money forces him to take a second job, which begins to affect his work at Dunder Mifflin. After tasking Oscar with looking into his books, and faced by his massive debt, Michael decides to run away, jump onto a moving freight train, and skip town to begin a new life.
However, as soon as he hops onto the train, it stops, and while he’s waiting for it to depart from the station, Jan finds him and talks him out of it.
HIGHEST: RECEIVING A GOLD MEDAL AT THE OFFICE OLYMPICS
When Michael is out of the office for the titular inter-office sporting events in “Office Olympics,” he has a really bad day. And when he returns to the workplace, Jim can tell that he needs a pick-me-up. So, he finishes the Office Olympics and gives Michael a gold medal.
The scene in which Michael is praised by his employees with a tear in his eye marked the writers taking the first steps towards making Michael a sympathetic character.
LOWEST: GETTING ROASTED BY THE OFFICE
After finding out that he is the cause of the office-wide stress epidemic that gave Stanley a heart attack during Dwight’s immersive fire drill, Michael decides to put on a Comedy Central-style roast in his own honor to let them blow off some steam. While the audience cheers for each roaster, Michael is heartbroken to hear all of his flaws pointed out and see his co-workers’ true thoughts about him exposed.
At the end of the roast, Michael steps up to the podium to speak (“You really went after my intelligence there...”) and bursts into tears before his first punchline. To add insult to injury, he knocks over his rimshot drum on his way off the stage.
HIGHEST: ROASTING EVERYBODY BACK
The day after his brutal roast, Michael doesn’t come into the office. Everybody realizes their jokes might’ve been a little too harsh. And then, after feeding some ducks at the park, he returns to the office to roast them all back. He jabs at everyone in the office with a one-liner takedown and says, “Boom, roasted!”
Stanley is the first to start laughing — appropriately enough, given that his heart attack was the reason why Michael let everyone roast him in the first place — and then the whole office s in. Michael brings everyone together with comedy, which has always been his dream. He’s applauded as he departs into his office.
LOWEST: GETTING DUMPED BY HOLLY
In the episode “Employee Transfer,” Holly is moved to the Nashua branch because she and Michael hid their relationship from David Wallace. They plan to continue in a long-distance relationship, but when they get to Holly’s new house in Nashua, she decides that it won’t work and breaks things off.
Michael is filled with despair on the ride home with Darryl, who teaches him how to sing the blues to deal with his problems.
HIGHEST: SELLING THE MICHAEL SCOTT PAPER COMPANY
Towards the end of Season 5, Michael leaves his job at Dunder Mifflin and starts his own paper company. It was one of the show’s best ongoing storylines. Michael recruited Pam and Ryan, and they began poaching clients from Dunder Mifflin with unsustainably low prices. So, David Wallace and Charles Miner offered to buy them out.
Michael leveraged David for more money as well as his old job back, a sales position for Pam, and a temp job for Ryan, and it was great to see him win. Michael proved he’s smarter than people think when he told David, “I don’t think I need to wait out Dunder Mifflin. I think I just need to wait out you.” The look of pride on Pam’s face is touching.