Michael Scott is a character that you might love or you might hate, but there’s no denying that he has made us all cringe from time to time. While Michael tried to be likable, he often tried too hard and his antics made fans of The Office laugh but also feel secondhand embarrassment. Michael Scott wanted to be the best boss ever, and he wanted to be funny.
However, he often crossed lines into territory that wasn’t funny, and he did a lot of things over the years that were pretty awful when it comes down to it. Here are 10 of the worst things that Michael Scott did on The Office.
10. WHEN HE HAD JO BENNETT BRING HOLLY BACK TO SCRANTON
Michael and Holly were really cute together, so when David Wallace broke them apart by sending Holly to Nassau, it was pretty sad. Michael never got over Holly as she was the only woman he was every in a healthy relationship with. In season seven, he asks new CEO Jo Bennett if she could transfer Holly back to Scranton.
While fans were happy when everything turned out for Michael and Holly, it wasn’t cool that he tried to interfere in her life like that. Holly had been living in Nassau and had a long-term relationship there; it seems she should have had more say in this situation.
9. FORCING OSCAR TO KISS HIM
Michael Scott, like many of the characters on The Office, was often a caricature of people and behaviors that many real-life people encounter in the workplace. While he might not have meant harm, he was rather ignorant about many social issues. In the "Gay Witch Hunt," Michael exhibits a lot of homophobia.
Then, to prove he’s not homophobic, he forces a kiss onto Oscar. This moment was awkward, to say the least, and even veers into sexual harassment territory.
8. SCOTT’S TOTS
This episode is one of the cringiest of the entire series. Michael Scott wants people to like him so badly that he will make promises that he can’t keep. Michael promised a kindergarten class that he would pay their college tuition if they stayed in school. Cut to ten years later and Michael doesn’t have the money.
He has to tell these high school seniors that he broke his promise. This is a horrible thing to do and left these students to suddenly scramble to figure out how to pay for college. This is one instance where Michael’s eccentric personality was just awful, not funny.
7. HIS TREATMENT OF TOBY
It’s no secret that Michael Scott doesn’t like Toby Flenderson. Throughout the series, he makes this very clear. While at times this could be funny, there were many instances where his hatred of Toby crossed the line. For one thing, he once attempted to frame Toby by planting marijuana on him. Luckily, Michael was so incompetent this didn’t turn out.
There was also the time he said that if he had a gun with two bullets and was in a room with Toby, Hitler, and Bin Laden that he would shoot Toby twice. This was definitely too far.
6. DIVERSITY DAY, AND DIVERSITY IN GENERAL
There were many times throughout the series where Michael was completely ignorant and even downright offensive when it came to race issues. In the first season, we see this clearly during the “Diversity Day” episode.
Michael goes so far as to do an offensive impression of an Indian man in front of Kelly Kapoor. This is just one of many times were Michael exhibits casual racism.
5. “THAT’S WHAT SHE SAID,” ETC.
That’s what she said might be the most well-known and quoted joke from The Office, but there are definitely issues with how Michael Scott used it. While in certain contexts, the joke could be funny, there were other times when his use of the joke bordered on sexual harassment.
This joke combined with other instances where Michael made female employees uncomfortable shows that Michael definitely needed to learn how to show respect for women.
4. WHEN HE FAKE FIRED PAM AND ERIN
While Michael cared about his employees and even insisted that they were all family, he didn’t always treat his employees well. Sometimes, Michael would take a joke too far and end up really hurting people’s feelings.
This was apparent during the scene where Michael fake fires Pam after they returned to Dunder Mifflin after starting the Michael Scott Paper Company. He then turned around and did the same thing to Erin.
3. HIS RELATIONSHIP WITH JAN
Michael's entire relationship with Jan was full of cringe moments. While Jan was just as horrible to Michael, this doesn't excuse Michael’s missteps where Jan is concerned. To start with, he slowly started dating her again after she got a boob job.
Also, he tried to send a semi-nude picture of Jan to the horrible Todd Packer but then accidentally sent it to the entire warehouse. While that might have been an accident, he shouldn’t have been sending that picture to Packer in the first place.
2. WHEN HE KEEPS DATING DONNA AFTER FINDING OUT SHE’S MARRIED
After his relationship with Holly, Michael struggles to find a relationship that’s healthy. He briefly dates a woman named Donna, but he soon finds out that she is married. He tries to justify by saying that her husband is probably a bad person. He does do the right thing and breaks up with Donna, but he doesn’t do so right away.
1. HIS INABILITY TO UNDERSTAND BOUNDARIES IN GENERAL
The biggest issue with Michael Scott is that he doesn’t understand boundaries at all. He thinks it’s funny to push people’s boundaries and doesn’t realize when he is crossing lines. This manifests in many ways in the series.
He often makes jokes about people’s appearance, picking on Phyllis and Kevin especially. He also tries to insert himself into Pam and Jim’s relationship. To top it all of, he doesn’t understand that there should be some professional boundaries between co-workers and their boss.