Michael Scott’s (Steve Carell) approach to the typical workday was always a tad unorthodox, but it was his untoward sense of humor that left audiences beside themselves with laughter. Scott’s clueless nature, political incorrectness and inability to keep his foot out of his mouth somehow didn’t dampen his likeability. Rather, it endeared him to many fans.

Flanked by his able-bodied assistant to the regional manager Dwight Schrute (Rainn Wilson) and the loveable couple Jim Halpert (John Krasinski) and Pam Beesly (Jenna Fischer), along with a cast of misfit and hilarious characters, Scott’s Dunder Mifflin branch on The Office (2005-2013) entertained audiences with it hysterics for nine seasons.

There were countless side-splitting instances of hilarity that could have easily made this list, because of Michael’s ability to inadvertently avoid aptness. So, with that in mind, here are the 16 Most Inappropriate Things Michael Scott Has Done.

16. “That’s What She Said”

the office1 The Office: 16 Most Inappropriate Things Michael Scott Has Done

Michael considered himself the king of forwards when it came to hilarious emails. Unfortunately, in a workplace like Dunder Mifflin, an attachment like “50 Signs Your Priest Might Be Michael Jackson” might not go over too well with employees or corporate.

Already infamous for his catchphrase “That’s what she said,” Michael had skirted the boundaries of sexual harassment many times in the first two seasons of The Office. In the season two episode “Sexual Harassment” (2005) Michael’s limits were tested when Toby (Paul Lieberstein) did a review of the company’s policy on the matter, and a lawyer was sent in, which threatened the future of email-inspired comedy.

Michael carefully explained that he didn’t create the forwards, he simply passed them on for others to enjoy. Mr. Scott’s logical comparison: “You wouldn’t arrest a guy who was just delivering drugs from one guy to another.”

15. Burned His Foot On the Grill

Michael Scott burns his foot on George Foreman Grill The Office: 16 Most Inappropriate Things Michael Scott Has Done

In the season two episode of The Office, “The Injury” (2006) Michael Scott burned his foot on his George Foreman Grill. Wait – what?

Yes, Mr. Scott liked his breakfast in bed, and the smell of smokey bacon, but he didn’t have a butler. So, he had to do everything himself, as he so lovingly explained to Jim and Pam over the phone.

Scott laid out six strips of bacon each night, before bedtime. Then he would wake up every morning and start up his grill, which just happened to be in the floor right next to his bed. As his breakfast sizzled next to him, Michael went back to sleep until his meal was ready.

On that particular morning, Michael woke and completely forgot about the scorching grill. As he got out of bed, he literally cooked his foot as the lid clamped down on his appendage. Hysterical, he called the office and begged for someone to come and pick him up, because of his self-inflicted injury.

14. Jan Levinson

Michael Scott and Jan Levinson  The Office: 16 Most Inappropriate Things Michael Scott Has Done

Michael Scott and Jan Levinson’s (Melora Hardin) rocky association crossed the line from strictly a working relationship to something more romantic after the pair closed a high-profile client account in the season two episode “The Client” (2005). Jan was so elated afterward that she kissed Michael and spent the night with him.

According to Levinson, the pair only talked. But in the season three episode “Back from Vacation” (2007), Michael revealed to the whole office that he had spent his time away in Jamaica with his boss. Michael had accidentally emailed a half-naked picture of Jan to everyone in the company. And bragged that they finally had sex.

In season four, after Jan lost her job at corporate, the pair moved in together but it didn’t last long. Eventually, the couple split for good in the episode “Dinner Party” (2008).

Later, Jan was artificially inseminated and had a little girl named Astrid. Michael ended up with Holly (Amy Ryan) and they had children of their own.

13. Ran Over Meredith

Meredith from the Office  The Office: 16 Most Inappropriate Things Michael Scott Has Done

In the season four episode “Fun Run” (2007), Michael Scott was so optimistic with his outlook on life. He ended up in a relationship with his old boss Jan Levinson, and he was gushing about it with the documentary crew as he drove to work one morning.

Sadly, Michael was too busy looking into the camera lens to notice poor Meredith (Kate Flannery) in the parking lot. Michael hit her with his car and Meredith flopped onto the hood like a fish out of water. She just as swiftly rolled off the vehicle. She was hospitalized with a pelvic fracture soon after.

The doctors discovered that Meredith had rabies, while she was incapacitated. In response to the disease, Michael hosted a fun run for rabies awareness. Dwight, on the other hand, simply tried to comfort Michael by saying, “It’s only Meredith.

12. Diversity Day Disaster

Diversity Day the Office  The Office: 16 Most Inappropriate Things Michael Scott Has Done

Michael’s negligence toward proper office etiquette was on full display following his infamous rendition of a Chris Rock comedy routine, during the season one episode “Diversity Day” (2005). Corporate sent a consultant from Diversity Today named Mr. Brown (Larry Wilmore) to deal with the situation and to get Michael to sign a form acknowledging he learned something during the session.

Michael was enraged when he discovered that the seminar was solely held for him, because of the jokes he made. Michael handled the matter in the professional manner that he was so well-known for. He signed the document – as Daffy Duck.

After Brown departed, Michael held his own seminar: “Diversity Tomorrow.” He took index cards and wrote the names of different races, cultures, and religions on them, and had each employee place the cards on their foreheads. Michael then made everyone take part in a bizarre word association game to guess which race the other employees were.

11. The Ben Franklin Fiasco

Michael Scott confused in The Office The Office: 16 Most Inappropriate Things Michael Scott Has Done

Michael Scott was on a politically incorrect roll in the season three episode “Ben Franklin” (2007). After scraping some gunk off his wall socket with a metal fork, Michael gave himself a jolt and had an epiphany to impart his vast knowledge onto a son he didn’t even have. In a video, Michael demonstrated the wrong way to jump start a car, and then showed his boy-to-be the proper way to remove a bra by using Dwight as a model.

Later, in preparation for Phyllis (Phyllis Smith) and Bob Vance’s (Robert Shafer) wedding, Michael instituted Prima Nocta, which gave the king the opportunity to deflower the bride on her wedding night. After he almost immediately ended Prima Nocta, Michael focused on getting strippers for the respective bachelor parties.

Co-ed naked strippers were the only answer in Mr. Scott’s mind. The girls ended up with a Ben Franklin (Andrew Daly) impersonator who Jim tried to convince Dwight was the real Mccoy, while the guys ended up with the exotic dancer Elizabeth (Jackie Debatin).

10. Prison Mike

Prison Mike the Office The Office: 16 Most Inappropriate Things Michael Scott Has Done

In the season three episode “The Convict” (2006), Michael Scott discovered that one of his new employees, Martin (Wayne Wilderson) from the Stamford branch, was an ex-convict. Naturally, Michael took it all in stride, as usual, by first ignoring the situation.

Later, Michael confided in Dwight before outing Martin to the entire office. Surprisingly, Martin was cool with everyone knowing. In fact, Martin described his time in prison in a way that made many of the employees, including Pan and Kevin (Brian Baumgartner), feel that they’d rather be in jail than at Dunder Mifflin.

Michael suddenly sported a purple bandana and created an alternate persona known as Prison Mike to dissuade his workers from thinking prison was better than his paper company. When Prison Mike failed, Michael Scott handled the manner in a logical and professional manner by locking his entire crew of employees in the conference room.

9. Fell in a Pond

Steve Carell as Michael Scott in The Office The Office: 16 Most Inappropriate Things Michael Scott Has Done

Michael Scott sure knows how to make a splash. In the season six episode “Koi Pond” (2009), Michael and Jim Halpert were sent on a sales trip to meet with a client, but things got a little out of hand when Michael fell in a Koi pond.

Michael tried to let everyone think he got caught in a freak rain shower, at first. But then he came clean and described the ordeal as, “these bunch of idiots that had put a fish tank in the ground with no cover and no railing.

Jim laughed about how long it took Michael to get out of the pond. The joke turned out to be on Mr. Halpert though when the video replay revealed Jim moving out of the way and letting Michael slip into the koi pond. Michael quickly forgave Jim once he discovered his friend was jealous of his sales reputation.

8. Sensitivity Training

15. When Michael Gets Visited By Trick Or Treaters The Office: 16 Most Inappropriate Things Michael Scott Has Done

After his harrowing ordeal in the Koi pond incident, Michael Scott was so embarrassed about the experience that he initiated a sensitivity training session. The idea behind his new initiative was that people couldn’t make fun of others for something they regretted.

Michael was further agitated once he revealed that not only had he fallen in the Koi pond but that he also took a dip in the fountains at the Steamtown Mall. Toby was so beside himself with laughter that he requested Michael kick him out of the meeting.

The idea didn’t quite set sail with the employees, because as Michael described it, “You can only make fun of things that they have control over, like Oscar is gay. That is his choice. We can make fun of that. I did not choose to fall into a Koi pond.

7. Drove into a Lake

Michael and Dwight the Office The Office: 16 Most Inappropriate Things Michael Scott Has Done

He certainly wasn’t Aquaman, but Michael Scott spent his fair share of time in the water on The Office. A couple of years prior to the notorious Michael/Jim Koi pond incident, Dwight found himself sharing his own watery adventure with his boss in the season four episode “Dunder Mifflin Infinity” (2007).

When Ryan (B.J. Novak) returned as the newest corporate suit, Michael and Dwight decided to drive from business to business delivering gift baskets to get their old clients back. After going 0-6 with their first handful of clients, Michael’s frustration manifested into yet another bone-headed decision on his part.

Michael’s GPS instructed him to turn right, but there was clearly nothing but a lake next to the car. Despite Dwight’s incessant warnings, Mr. Scott drove his vehicle smack into the water. Fortunately, neither man was hurt. Dwight tried to reassure Michael by asking, “Did you get the rental insurance?”

6. Would Shoot Toby Twice

Michael Would Shoot Toby Twice The Office: 16 Most Inappropriate Things Michael Scott Has Done

Michael Scott and Human Resources Representative Toby Flenderson were never going to be best friends, because Michael thought of him as a corporate drone that wasn’t part of his Scranton branch’s family. Invariably, if Michael did or wanted to try something inappropriate, Toby was rightfully there to interfere.

In the season four episode “Goodbye, Toby” (2008), Michael was elated to bid a forever farewell to Mr. Flenderson. He even had the common courtesy to ask security to escort Toby from the building at the end of the day.

In season five, Toby returned in the episode “Frame Toby” (2008) much to the dismay of Mr. Scott. If there was ever any doubt about his feelings for Toby, Michael cleared it all up in the season six episode “The Chump” (2010) by saying, “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.”

5. Karate Match with Dwight

Dwight from The Office  The Office: 16 Most Inappropriate Things Michael Scott Has Done

Jim Halpert had a reputation for pranking poor Dwight Schrute at every possible turn. But Pam Beesly’s heartthrob might have gone too far in the season two episode “The Fight” (2005). While arguing with Dwight, and as Michael walked by, Jim casually asked if Dwight could beat up the boss.

Michael scoffed at the idea, and later got on a kick about his ability to take a punch. When Jim refused to engage him, Dwight landed two quick jabs to Michael’s stomach that folded him up like a lawn chair. Feeling that Schrute sucker-punched him, Michael extended lunch by an hour so that the employees could watch the pair fight at the dojo.

During the sparring session, Michael managed to force Dwight to the mat and crawl on top of him. After several insignificant blows, Michael choked up a snot hocker to spit in Dwight’s mouth. The actual delivery of the booger didn’t appear on screen, but it was clear by Mr. Scott’s demeanor later in the office that he had won the fight.

4. Kissed Oscar

Michael Kissed Oscar The Office: 16 Most Inappropriate Things Michael Scott Has Done

There were moments when Michael Scott did the unthinkable. And then there were those instances when even the most stalwart fans of The Office were wondering WTF was he thinking. In the season three premiere “Gay Witch Hunt” (2006), Toby explained to Michael that Oscar (Oscar Nunez) was gay after Mr. Scott called him a derogatory name.

During his apology, Michael outed Oscar to the entire office. In an effort to avoid such a blunder in the future, Dwight recommended using “Gaydar,” which is a type of radar that Jim Halpert once told him about. Jim called personally to help his friends out, but surprisingly Sharper Image was sold out.

After Oscar told everyone he couldn’t work there anymore, he was forced to kiss Michael in the conference room in front of all his colleagues. Oscar decided not to quit, or pursue a lawsuit, once Jan offered him a three-month paid vacation and a company car. When he spoke to the documentary crew afterward, Oscar said, “Kids, sometimes it pays to be gay.”

This was by far one of Michael’s most idiotic moments on the show.

3. Started his own Paper Company

steve carrel michael scott office The Office: 16 Most Inappropriate Things Michael Scott Has Done

In the season five episode “Two Weeks” (2009), Michael Scott revealed in the fact that he had turned in his two weeks’ notice. But he didn’t take into account how lousy the job market would be. After failing to find employment, Michael decided to start his own paper company.

And in true Jerry Maguire (1996) fashion, Pam Beesly believed enough in her boss to join him in the venture. Wait – what? Yes, Beesly became a salesperson at the Michael Scott Paper Company. And after Michael recruited former temp Ryan Howard from the bowling alley, he had his dream team.

During the course of the five-episode story arc, unbelievably, Michael’s company forced Dunder Mifflin to buy him out. Michael got his, Pam, and Ryan’s jobs back at the office and forced David Wallace (Andy Buckley) to fire Vice President of the Northeast Region, Charles Miner (Idris Elba).

2. Scott’s Tots

The Office Scotts Tots The Office: 16 Most Inappropriate Things Michael Scott Has Done

Michael Scott tipped the scale of absurdity in the season six episode “Scott’s Tots” (2009). During a visit to a local third-grade class, 10 years prior, Michael had promised to pay for the college tuition of all the students if they graduated from high school.

The fateful day finally arrived, and after rescheduling seven times, Michael finally faced the music. When he arrived at the school, the students were draped in baby blue t-shirts with the words “Scott’s Tots” printed on them. One student called him his guardian angel, as Michael wept with regret for his actions.

Michael tried to substitute laptop lithium batteries as the award, but it was much to the chagrin of the fifteen disappointed students. Michael rode back to Dunder Mifflin with the new secretary Erin (Ellie Kemper) who tried to reassure him by saying, “if you hadn’t made that promise, I think a lot of them would have dropped out.”

1. Left The Office!

The Office Lecture Circuit 1 The Office: 16 Most Inappropriate Things Michael Scott Has Done

Despite all his blundering and political incorrectness over the years, Michael Scott’s worst mistake was when he decided to move to Colorado to be with Holly in the season seven episode of The Office titled “Goodbye, Michael” (2011).

Actor Steve Carell’s departure from the show was a damaging blow to the character structure holding the series together that ultimately diminished the quality of the final two seasons that followed. In an interview with Charlie Rose, Carell discussed his decision to leave the series. “It wasn’t an easy decision to make, but I just feel like now’s the time. And I actually think it will be good for the show in the long run.”

Fortunately, for all the fans, Carell did return for the series finale in 2013. Jim Halpert surprised Dwight Schrute on the day of his wedding to Angela (Angela Kinsey) with his new best man – Michael Scott. And although he only appeared in a few scenes, Michael’s arrival sent the successful series out with much fanfare.

Which of Michael Scott’s WTF Moments in The Office do you think are the strangest? Let us know in the comments!

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