Across seven seasons of the cringiest moments in the show’s history.
But he also has a huge heart. He believes in his people and sees his staff as his family, treating Ryan like a son and Erin like a daughter. Most of the time, Michael is lovable. But sometimes, he’s not so lovable. So, here are the five best and five worst things that Michael Scott ever did.
Best: Attending Dwight’s Wedding
The producers of The Office remained tight-lipped about whether or not Steve Carell would be returning for the series finale in the months leading up to his airing.
Michael Scott was expected to return, as the series couldn’t really have ended in good faith without him, but we didn’t know for sure until he showed up to be Dwight’s best man in Jim’s sweetest prank.
Worst: Kissing Oscar
In the season 3 premiere 'Gay Witch Hunt', Oscar is outed after Michael accidentally uses homophobic language towards him. Michael spends the whole episode desperately trying to let Oscar know that he’s okay with his sexuality – and, of course, he makes the situation much, much worse.
At the episode’s excruciating climax, Michael kisses Oscar in the conference room in front of his other employees. This ended up paying off very well for Oscar, as he was given a paid vacation and a new company car.
Best: Giving Pam A Sales Position
When Michael left Dunder Mifflin to start his own paper company, the only co-worker who went with him following his Jerry Maguire-esque request was Pam. She didn’t want to be a receptionist anymore; she wanted to be a salesperson.
A few short weeks later, Michael was selling his company to Dunder Mifflin after stealing some of their biggest clients and negotiating jobs for himself, Pam, and Ryan. He could only make one of them a salesperson and gave the position to Pam.
Worst: Hitting Meredith With His Car
“I feel very blessed!” In the season 4 premiere, 'Fun Run', Michael tells the camera what he’s been up to during the summer hiatus as he drives into work. When he pulls into the parking lot, there’s a loud bang and Michael jumps with a start.
He looks through the windshield and sees Meredith rolling off the hood of his car. It was an accident, but it was still a pretty terrible thing to do. And he brought it up to the office in the worst way possible.
Best: Being A Father Figure For Erin
Erin is one of the most lovable characters from The Office. She grew up in a series of foster homes, so she never really had stable parental relationships. Instead, she sought a father figure in Michael.
At first, Michael didn’t build a great relationship with Erin. However, as he came to realize that Erin viewed him as a father figure, Michael committed to the role, leading to some of his sweetest moments.
Worst: Proposing To Carole At Diwali
When Kelly invited her co-workers to her Diwali celebrations, Michael asked his girlfriend Carole to come along. After meeting a couple who got an arranged marriage, Michael is inspired to take up the microphone and propose to Carole in front of dozens, maybe even hundreds of people.
It’s painfully cringeworthy to watch Carole’s rejection; it’s just good to know that Steve and Nancy Carell are happily married in real life and the cringe is confined to the screen.
Best: Proposing To Holly
In the season 7 episode 'Garage Sale', Holly realizes she needs to go back to Colorado to be with her ailing father and her struggling mother, so Michael decides to propose to Holly and move to Colorado with her.
His initial plan involves writing a message in gasoline in the parking lot and setting it on fire, but Pam talks him into changing the plan to an equally romantic, but much safer proposal.
Worst: Dating Pam’s Mother
At Jim and Pam’s wedding, Pam’s dad brought his young new girlfriend, which drove Pam’s mother into the arms of another man: Michael Scott. Pam was horrified to discover that Michael was dating her mother, at which point he pledged to start “dating her even harder".
What might be even worse than dating Pam’s mother is that Michael dumped her when he found out she was a few years older than him.
Best: Going To Pam’s Art Show
In season 3’s 'Business School', Pam invites everyone from work to an art show she’s putting on with her painting class. Oscar shows up with Gil to harshly critique Pam’s work behind her back, and Roy brings his brother in an obvious attempt to look like a good boyfriend without actually being one.
Just when Pam’s about to give up her dreams and go home, Michael arrives, apologizes for being late, and showers her work with praise. He asks if he can buy her painting of the building so they can hang it in the office.
Worst: Promising College Tuition He Couldn’t Afford To Scott’s Tots
In the running for The Office’s cringiest episode, season 7’s 'Scott’s Tots' sees Michael’s worst mistake catching up with him. On a visit to a school, Michael promised a bunch of third-graders that he’d pay for their college education if they graduated.
However, Michael couldn’t afford to pay for their tuition, and when it came to the kids’ graduation, he still couldn’t afford it. So, he had to go into the school and tell them the bad news in person.