The Office, 20 years: Celebrating 20 years of The Office: Top 5 Michael Scott’s most inappropriate moments as the boss

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Despite being the regional manager of the Dunder Mifflin Branch in Scranton, Michael Scott in The Office lacks management skills and is often ignorant about social conventions. He would come out with cringy and inappropriate jokes, creating an uncomfortable atmosphere for everyone at the workplace. Michael was portrayed by Steve Carell in the hit comedy series The Office on NBC.

Michael plays the role of the manager at a fictional paper company in Pennsylvania. Though he may occasionally show a side of vulnerability and good leadership skills, his unprofessional antics make him one of the least favorable people in the room. Let's take a look at some of the most misguided Michael Scott moments from The Office, which first hit the screens 20 years ago.

Top 5 Michael Scott’s most inappropriate moments as the boss

5) Locks up the employees to teach a lesson

The Convict – Season 3, episode 9

Michael tries his hardest to show that he is welcoming of all races at the workplace. When the Dunder Mifflin Stamford merges with the Scranton branch, Michael comes to know that the Black employee Martin Nash (played by Wayne Wilderson) had done jail time for insider trading. Martin talks to the employees about his time in prison. Some of the employees say that prison sounds better than the office, which affects Michael.

“The worst thing about the prison was the dementors.”

Michael takes on a character called ‘Prison Mike’ and explains to everyone all the bad things that happen in prison. But he has no proper knowledge and ends up making up a lot of bizarre scenarios. When no one takes him seriously, an infuriated Michael ends up locking all the employees inside the conference room. Toby (played by Paul Lieberstein) later releases the staff and tells Michael they were just joking. Martin ends up quitting.

4) Encourages discussion on killing an employee

The Chump – Season 6, episode 25

Michael’s hatred for Toby is well-known, and he doesn’t hesitate to show his contempt towards him at every possible chance he gets. In the episode, all the employees are in the conference room, where Toby is heading a meeting about radon test kits.

“If I had a gun with two bullets and I was in a room with Hitler, Bin Laden, and Toby, I would shoot Toby twice.”

Michael says that his meeting is extremely dull and that all the employees will die of boredom before radon gets them. To show his frustration, Micheal states that if Osama Bin Laden, Hitler, and Toby were in a room and he had two bullets, he would shoot Toby twice. Dwight (played by Rainn Wilson) volunteers to help with this imaginary scenario. He gets Phyllis (played by Phyllis Smith), Andy (played by Ed Helms), and Toby to line up to see if one bullet can kill them all. Everyone claps at the solution, leaving Toby looking dejected.

3) Fires an employee as a joke

Pilot – Season 1, episode 1

Michael Scott is a manager who would often misuse his powers for his own amusement. In the episode, the Dunder Mifflin company is considering downsizing, and the employees in the office are on the edge. Meanwhile, Michael is trying his best to impress the new temp at the office, Ryan (played by B. J. Novak).

“I guess the atmosphere that I've tried to create here is that I am a friend first and a boss second, probably a entertainer third”

Trying to show off his authority, Michael informs Pam (played by Jenna Fischer) that because of downsizing pressure he has to let her go. When she asks why, he tells her that she has been stealing Post-it notes. Ryan is visibly uncomfortable witnessing this. Pam gets upset and starts crying, making Michael realize that his prank may have backfired. An angry Pam lashes out at Michael and walks out.

2) Hits an employee with his car

Fun Run Part 1 and 2 – Season 4, episode 1/2

Michael can often be reckless not just with his words but also with his actions. When Michael arrives at work in the morning, he hits Meredith (played by Kate Flannery) with his car accidentally. She ends up getting her pelvis fractured. Ryan, who is now Michael’s boss, is worried about a lawsuit.

“Guess what, I have flaws. What are they? Oh, I don't know. I sing in the shower. Sometimes I spend too much time volunteering. Occasionally I'll hit somebody with my car. So sue me... No, don't sue me. That is the opposite of the point that I'm trying to make.”

Michael, who still feels guilty, decides to do a charity fun run for Meredith called,

‘Michael Scott's Dunder Mifflin Scranton Meredith Palmer Memorial Celebrity Rabies Awareness Pro-Am Fun Run Race for the Cure.’

But he is unsuccessful in getting enough donations. After the run, Michael ends up in the hospital due to dehydration. He is visited by Meredith, who decides to forgive him.

1)Tries to kiss an employee

Diwali – Season 3, episode 6

Michael asks everyone in the office to be supportive of Kelly (played by Mindy Kaling) and take part in the local Diwali celebration. At the festivities, Michael turns up with his girlfriend, Carol (played by Nancy Carell). He makes the impromptu decision to propose to Carol in front of everyone. But Carol is taken aback and rejects him.

“We’re both victims of broken engagement.”

An upset Michael talks to Pam after the event. Pam had just come out of an engagement. Michael mistakes her wanting to connect on failed love lives as a signal and makes a move to kiss her. A shocked Pam immediately rejects him, leaving Michael embarrassed.

The Office is filmed in a mock-documentary format that explores the daily lives of the employees and their exaggerated office interactions at Dunder Mifflin Scranton.

The Office is available on the streaming platform Peacock.

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