The Worst Things Michael Scott Ever Did On The Office

Michael Scott (Steve Carell) was a fixture on "The Office" for seven seasons, where he served as the lovable idiot boss of Dunder Mifflin's Scranton branch. Viewers of the show saw Michael at his worst and his best — but unfortunately, it was a little too much of the former. While he genuinely seemed to care for his employees, there was no one he cared about more than himself — until Holly Flax (Amy Ryan) changed him for the better, further down the line.

If someone else became the center of attention, Michael always just had to get the spotlight back on him. He was the king of crossing the line, burdened by an uncanny ability to take things too far, fueling many episodes filled with awkward, cringe-worthy moments. While there were plenty of times when we saw his sweet side and a proclivity to do the right thing, he too often would do the opposite, hurting people with his self-centered mindset. 

Nevertheless, many of these instances were as real as they were painful to watch unfold. These are some of the worst things the Dunder Mifflin manager ever did on "The Office."

In Season 3, Episode 1 ("Gay Witch Hunt"), Michael outs his co-worker Oscar Martinez (Oscar Nunez) to the entire office. The initial outing happens accidentally when Michael refers to his coworker as a gay slur for preferring "Shakespeare in Love" over "Die Hard." Toby Flenderson (Paul Liberstein) reveals to Michael that Oscar is actually gay, which comes as a surprise to the Dunder Mifflin boss. Michael later apologizes to Oscar, but the situation doesn't end there.

Michael pulls Dwight Schrute (Rainn Wilson) into his office to identify other gay people at the branch. While that might be disturbing in its own right, believe it or not, that isn't the worst thing Michael does in the episode. The employees slowly start to find out about Oscar, which makes the accountant feel discriminated against by some colleagues. Michael calls a meeting to shut this down, and he forces Oscar to come out to all of his coworkers. To prove how okay he is with Oscar being gay, he tries to hug his subordinate in front of the other employees.

When Oscar refuses, Michael starts crying and apologizes for calling Oscar the slur earlier in the episode. To "raise the stakes," Michael then kisses Oscar to show that he's accepting with who he is. It's a genuinely uncomfortable moment, something that would not fly in today's workplace — in fact, something that has never been a god idea in a workplace. His outing of Oscar, mixed with the forced kiss, has to rank as one of Michael's worst managerial moves.

At the end of Season 4, Toby leaves Dunder Mifflin to move to Costa Rica, much to the pleasure of Michael. That happiness is relatively short-lived, however, as the mild-mannered HR rep returns to his job in Season 5, Episode 9 ("Frame Toby") and crushes Michael. After finding out that his nemesis is back, Michael becomes determined to get rid of him, carrying out all sorts of absurd plans. Each attempt is more insane than the one before, with Michael even trying to force a physical interaction between Toby and Pam Beesly (Jenna Fischer) to get the former fired for sexual harassment.

As if that's not horrible enough, Michael then takes his plan to the next level, attempting to frame his co-worker. He seeks out some Vance Refrigeration employees, buys what he thinks is $500 on two pounds of "weed," then plants the supposed drugs in one of Toby's desk drawers, encouraging Dwight to call in an anonymous tip to the police. When the cops show up, they go through Toby's desk and find a Ziploc bag with green stuff inside. Michael immediately takes the blame, because he has a change of heart — and the cops reveal that it's just Caprese salad.

Trying to frame someone for drugs is absolutely reprehensible, and in many ways Michael got what he deserved by losing $500 on a bag of salad. While it's fun to laugh at Michael and say he learned his lesson, just think about how differently the story could have ended, however, if he actually procured some real weed.

Under the direction of David Wallace (Andy Buckley), Michael once traveled to a small, local paper company called Prince Paper to take away some of their clients. Pretending to be a local business owner in need of a paper supplier, he brought along Dwight, posing as a salesman looking for a job. Michael entered first, began quizzing the owner about his business, then snapped a photo of their client map. But the Prince family, apparently some of the sweetest people on the planet, were so kind that it made Michael feel conflicted about stealing their customers.

In the end, he gave in to the pressures of his boss, bringing David the intel. While the ensuing blowback to the small paper company wasn't immediately revealed, "The office" later showed that when Michael quit Dunder Mifflin, he called Prince Paper looking for a job — and their voicemail said they'd gone out of business. 

So in essence, Michael likely contributed to the closure of a hardworking family's business. Dunder Mifflin likely could have carried on just fine without taking their clients, but this all feels like yet another instance of Michael choosing the wrong path.

If you're a superfan of the series, you knew this one was coming. The "Scott's Tots" episode in Season 6 is regarded as one of the hardest episodes to watch on "The Office." It is 22 minutes of pure cringe, and because of that is often treated like a horror movie — skipped over by fans, or at the very least endured through the cracks between fingers. 

The plot reveals that Michael promised some third-graders 10 years ago that he would pay their college tuition if they graduated high school. Now that a decade has come and gone, it's time to face the music, and Michael has to tell these now-teens that he hasn't quite achieved the level of success and affluence that once seemed like something worth banking on. He takes Erin (Ellie Kemper) with him to their school, where the kids perform a song for him, proclaiming he's made their "dreams come true." Michael winces during the entire song (as does anyone watching the episode), and he is forced to eventually reveal the truth: he won't be able to pay for any of their higher educations.

Making matters worse, he offers them free laptop batteries — because that's the same as four years of tuition, right? Making a promise he could never fulfill — especially one of such immense magnitude — is one of the more reprehensible things Michael has ever done in his life.

Michael's girlfriend Donna (Amy Pietz) appears in four episodes of Season 6, the first of which came in "Happy Hour." The pair first met at the bar/lounge that Donna managed, and she later came to Dunder Mifflin in "Body Language" as a potential customer. After some awkward flirting at the office, the pair kissed at the end of the episode, officially becoming a couple in "The Cover-Up." In that episode, some of the women in the office became suspicious of Donna — primarily Kelly Kapoor (Mindy Kaling) and Pam — thinking that she was cheating on Michael.

Of course, Michael didn't want to believe it, so Pam had to show her boss photos of Donna and another man, forcing Michael to accept the truth. He then stalked the man — who turned out to be Donna's husband — at a baseball game he coached. 

Making matters worse, Michael continued to date Donna, even though he knew she was married, pretending to break up with her just to get his co-workers off his back. Eventually, in "The Chump," Michael finally backed out of the relationship, breaking up with Donna in the most cowardly of ways: via text message. All around, not Michael's finest moment.

The way Michael treats women throughout his seven years on "The Office" is nothing short of abhorrent. The man was constantly walking the fine line of sexual harassment, and most of his offenses, if committed in a real life workplace, would have him out on the curb carrying a cardboard box. There are countless examples of such behavior to choose from, making it absolutely incredible that he held this job for seven seasons — and also ironic that the laziness of his perceived nemesis, HR rep Toby, was probably the only reason Michael continued to be employed.

Several times, Michael made comments about Pam's breasts, even suggesting that she unbutton her blouse more. His constant "that's what she said" jokes were funny — but also intrinsically sexual in nature and, therefore, not appropriate for the workplace. Additionally, Michael was constantly judging the women in the office on their physical appearance — calling Pam and Karen Filippelli (Rashida Jones) hot while making negative comments about Phyllis (Phyllis Smith) and Angela's (Angela Kinsey) appearances.

Michael frequently "fake fired" people on "The Office," seeming to enjoy the power he held over the fates of others. 

The first instance came in Season 1, when he pretended to fire Pam in front of Ryan (B.J. Novak). For some reason, this was hilarious to Michael, who never seems to understand how much he's hurting the person he is pranking. In that instance, after telling Pam he was just kidding, she called him a jerk and began to cry, leaving him acting offended. 

He clearly didn't learn from this, as in a later episode when Dunder Mifflin absorbed the Michael Scott Paper Company, and he once again told Pam she had lost her job — this time, a highly-valued sales position she had supposedly ceded to Ryan.

But the fake firings didn't stop at Pam. Perhaps thinking he was on a roll after messing with Pam for a second time in Season 5, Michael had her call Erin (Ellie Kemper) into his office so he could play the same prank on her. Not only did he tell her that he had to let her go, but Michael also mentioned to Erin that by the way, no one in the office liked her. In Michael's mind, a laugh and assurance it was all a joke made everything all right — but even though the sweet Erin laughed it off alongside him, he had nonetheless planted a hurtful seed that seemed to imply Erin's colleagues hated her.

Michael clearly has done some pretty terrible things at Dunder Mifflin, but who knew he'd go so far as to kidnap someone? 

In Season 4's "Launch Party" two-part episode, Michael and the gang were preparing to live-stream from their office with the company's other branches. It was all intended to be part of Ryan's big website launch extravaganza, but things took a dark turn in Scranton when Michael became displeased with the pizzas delivered to their building.

When told he would not be receiving his eight pizzas for half off, Michael impulsively held the delivery driver hostage in the conference room. The branch manager said he would only release the hostage when he received his discount. 

Panicked, the other Scranton employees begin researching laws on kidnapping, false imprisonment and their own culpability as possible accessories to the crime. Thankfully, after the driver alerted the company on their livestream that he was being held against his will, Michael and Dwight managed to turn the driver free, paying full price for the pizzas. But at moments like this, you wonder how Michael Scott isn't serving serious jail time for any of these shenanigans.

Viewers immediately became aware of Michael's awkward ineptitude, as no less than Episode 2 of "The Office" was centered on it. Titled "Diversity Day," the show set the tone-deaf level of Michael's character, one that would carry him all the way from Season 1 through Season 7. 

In the now-classic episode, a lecturer is brought in to talk about diversity in the workplace — but, unhappy with the lesson, Michael believes he can do better, taking over the workshop and sending the man on his way.

Michael then decided to write down different ethnicities and races on index cards, making his employees pick one at random and put it on their heads. The workers were then expected to uncover the words on their foreheads by conversing with one another. Naturally, the delicate exercise goes south quick, with most employees employing racist stereotypes to help one another guess what's on their card. 

Of course, Michael was the worst abuser. He ended up doing a horrible impression of a convenience store worker while talking to Kelly Rajanigandha Kapoor — who didn't even have a card on her head. She rightfully slapped him for mocking her Indian heritage, but he should have gotten a much bigger punishment for how he handled the entire exercise.

Season 6, Episode 1 ("Gossip") was the episode where we discovered that Stanley Hudson (Leslie David Baker) was having an affair. The office interns informed Michael that they saw Stanley at a club with a woman, and Phyllis later confirmed that Stanley's wife was out of town. Once he put the pieces together, Michael began telling the entire office about their co-worker's indiscretion, and when Jim Halpert (John Krasinski) told him such behavior was is inappropriate, Michael of course came up with an idea that only made things worse.

Spreading rumors about everyone in the office, Michael was convinced that this blanket of false gossip would throw everyone off the trail of Stanley's affair. Technically, the diversionary tactic worked — even when Michael later revealed that only one of the office rumors was accurate. Pam and Jim stepped forward, admitting they were pregnant, thereby saving Stanley from being painfully outed a second time.

Constantly searching for a girlfriend, Michael found one in Pam's mother Helene (Sasha Alexander) in Season 6. The pair began dating while Jim and Pam were on their honeymoon, and when they returned, all hell broke loose. While the entire office agreed that the relationship was over the line, however, it didn't stop Michael from pursuing things further.

Pam begged her boss to break up with her mom, even going so far as to slap him in the face. Two episodes later, Jim and Pam tried to make the best of the difficult situation, going on a double date with Michael and Helene. But Michael always has to kick things up a nasty notch, and in this case he broke up with her at lunch in front of Jim and Pam when he realized Helene was older than he thought. 

All in, not only did Michael make the ethical mistake of dating one of his employee's mothers, but he then doubled down by crushing the poor woman on her birthday, for being too old. Bad form, Michael.

In Season 7's "Classy Christmas," Holly returned to the Scranton branch after having left in Season 5. Unfortunately, Holly was still with her boyfriend A.J. (who Michael met in the "Company Picnic" episode), and the Dunder Mifflin manager was having a hard time coming to terms with it. When she came back to work, Holly showed Michael a Woody doll that A.J. had given her after watching "Toy Story" for the first time. The doll obviously meant a lot to her, as she kept the cowboy on her desk — but it's not long before she finds him vandalized.

Michael, unable to cope with Holly's relationship status, had of course trashed the Woody doll, covered it in food, and threw it in the trash. When she questioned the office about it, Michael then attempted to blame Toby — but the truth was clear. Eventually, Michael caved, yet still insisted the vandalization was part of Christmas party festivities, saying it was all a joke. 

Eventually, Michael admitted he was jealous, apologized and cleaned off Woody. But still, this was an extremely vengeful, childish act, and one of the points in the show that depicted how cruel Michael could be when things didn't go his way.

Kelly certainly loves getting attention in the office, but she doesn't hold a candle to Michael. The manager is constantly trying to get all eyes on him, no matter the situation. 

This was most evident when Phyllis got married in Season 3, with Michael pushing her father down the aisle in his wheelchair. When the trio made it halfway down, her father stood up dramatically, struggling to walk his daughter to the alter as the guests erupted in applause. This should have been a tender, inspirational moment — one Phyllis would never forget — but instead, it became an unforgettable moment for a far worse reason.

Aggravated, Michael looked at the camera and said "this is bulls**t," continuing to kick the wheelchair toward the end of the aisle.

Later, while Phyllis and Bob were exchanging vows, Michael interrupted — one of the biggest no-no's at any wedding. He attempted to introduce the couple for the first time (before Bob had even said his vows), then screamed as the couple shared their first kiss. Years later, at Pam and Jim's wedding, he once again showed an inability to let anyone else be the center of attention for a moment, orchestrating a dance down the aisle that once again made him the focus rather than the bride and groom.