Michael Scott might think he's the world's best boss and a total ladies' man, but really,
he's racist, sexist, and super selfish. And for every moment he does something nice for
one of his employees, there are a zillion more in which he's incredibly cringey.
Until settling down with Holly Flax, Michael Scott's love life involved a series of destructive
and disastrous relationships, like the time he broke every workplace rule by dating Helene
Beesly, Pam's mom. After meeting at Jim and Pam's wedding, Michael and Helene hit it off,
much to Pam's horror. Eventually, Jim and Pam are forced on a double date with Michael
and Helene. When Pam sees how happy her mom is with Michael, she warms up to the idea
that her boss might one day be part of the family. Unfortunately, the birthday party
is full of twists and turns, and while giving Helene a series of elaborate gifts, Michael
finds out his girlfriend's age, and suddenly realizes she's a lot older than him.
"You're 58 years old?"
"Uh-huh."
"Congratulations."
As a result, he begins looking for a way out of the relationship, right there in the restaurant,
on her birthday. Jim and Pam watch, mortified and shocked, as Michael lists all the reasons
he should split up with Helene, such as the fact that he wants to have kids, visit Italy,
and skydive, all stuff he probably should've discussed with his girlfriend before professing
his undying love to her. Obviously, the whole date is incredibly painful to watch, but at
least Michael gets his comeuppance when Pam slaps him across the face.
Michael Scott and Ryan Howard have always had a weird relationship. Michael wants to
be Ryan's mentor, his best friend, and occasionally, his lover. Unfortunately, this obsessive friendship
only goes one way, so Ryan manipulates his boss. Case in point, when Ryan brings Michael
to his business school so he can do a Q&A.
Michael can't wait to impart his wisdom to the next generation. Sadly, it's all a set-up.
Ryan has no respect for his manager or the paper business, and he knows the class will
eat Michael alive. Of course, Michael does a pretty good job of sabotaging himself, by
walking into the classroom accompanied by his own theme song. Plus, Michael is a big
believer in visual aids, and one of his teaching methods involves hitting a student in the
head with a candy bar. The most awkward moment comes when Michael explains the basics of
business to these MBA students, lecturing that,
"The more stickers you sell, the more profit, fancy word for 'money', you have to buy PlayStations
and Beanie Babies."
But once the students start asking questions, it becomes painfully obvious that Michael
is in way over his head. The final twist of the cringey knife comes when he discovers
that Ryan has betrayed him. It's a humiliating experience, but at least Michael gets the
last laugh by forcing Ryan to work alongside his least favorite person in the office, his
own girlfriend, Kelly Kapoor.
Michael Scott thinks he's a natural born leader, but he's also incredibly insecure. So whenever
an authority figure suddenly shows up, Michael gets super competitive. That's definitely
the case in Season 2 when Michael takes his employees on a booze cruise. Even before the
ship sets sail, Michael refuses to admit the fact that the captain of the boat outranks
the manager of the office.
In fairness, Captain Jack is a bit of a jerk himself, but it's his ship. And whenever Jack
tries to make an announcement or get a party game going, there's Michael, stealing the
mic and trying to spark a one-man mutiny. But things get really bad when Jack kicks
off the dance contest as Michael is giving a speech on leadership skills. Ever the master
of improv, Michael decides to go with the flow by taking over the dance
floor and giving everyone a motivational dance lesson.
With everybody starring in horror, Michael pulls out all of his best moves. He skips
and shakes, he's high-stepping and knee-slapping. He even throws in the worm for good measure.
Phyllis is so ashamed that she looks away, as other spectators bite their lips to keep
from laughing. But Michael is completely oblivious. As far as he's concerned, he's the real captain
of the ship, the best regional manager, and the king of the dance floor.
Give Michael Scott a microphone, and you're guaranteed to regret it. That's a lesson we
all learned the hard way in the Season 2 premiere, when Michael hosts the Dundies. An annual
awards show of Michael's own making, the Dundies show is supposed to reward the office
for their hard work. Instead, it's an opportunity for Michael to make everyone squirm in their
seats.
It all starts with a horrible hip-hop number, complete with cue card mishaps and tech issues.
Things get racial when Michael hands Kelly the Spicy Curry award and assumes the white
woman with Stanley isn't his wife. Both Phyllis and Angela win trophies that highlight parts
of the body best left unmentioned at work events, and Ryan realizes Michael's true feelings
for him when he's given the Hottest in the Office award.
Pam describes the horror of the Dundies perfectly when she compares it to a car crash, one that's
so bad you've got to stare at it, because your boss is making you.
In Michael Scott's defense, he isn't always a bad guy. Oftentimes, he means well, and
in certain rare moments, he can be pretty cool. For example, he's on his best behavior
in Season 6 when the office is hanging out during happy hour. In fact, when he meets
Pam's friend, Julie, he actually treats her like a real human being. He's funny, polite,
and charming, and the two really hit it off, until Michael learns that Pam brought Julie
along in the hopes of setting them up.
Once Michael realizes he's on a date, he morphs into one of his most obnoxious characters,
Date Mike.
"Date Mike. Nice to meet me."
Wearing a backwards Kangol hat and armed with tips from reality TV, Date Mike struts around
the bar with his chest hair exposed, tries tying a cherry stem with his tongue, only
to choke on it, and spins his pool cue around like he's some sort of slick hustler, a move
that majorly backfires when he sends drinks flying across the room.
The worst part comes when Date Mike climbs up on the pool table and starts dancing his
way across the felt. He even picks a fight with the bar owner before a bouncer shows
up. Once Date Mike is distracted, Julie heads for the hills, unimpressed by Michael's particular
brand of charm. From the moment he puts that hat on until he's playing his pool cue like
an electric guitar, we're all desperately hoping that Date Mike would just disappear.
Holidays are always interesting around the Scranton office. Sometimes there's a civil
war brewing in the Party Planning Committee, and occasionally a drunken Meredith will set
herself on fire. It's hard to get through the holidays without some sort of hilarious
drama, but during Season 3, things are especially sad for Michael Scott. He's just broken up
with his girlfriend Carol, so he decides to find a rebound.
Accompanied by his entourage of Andy, Dwight, and a reluctant Jim, Michael lets loose at
the restaurant, and both he and Andy manage to pick up two waitresses. A few scenes later,
the duo returns to the office Christmas party with their dates, but Michael ends up confusing
the two Asian women and can't remember which one is his date.
After he finally figures out which waitress he brought to the party, we're treated to
one of the most hysterical and humiliating Michael Scott moments. He brings his date
in for a big hug and then marks her arm with a magic marker, so that he won't ever get
the two women confused again. It's a new low for Michael Scott, and as always, the regional
manager has an unacceptable excuse, claiming that all waitresses look alike.
For all of his flaws, Michael Scott somehow runs the most successful office in Dunder
Mifflin. So when the Stamford branch shuts down, six employees are sent over to Scranton.
But thanks to Michael's unique personality, and a whole lot of office drama, the folks
from Stamford abandon ship, and the first to go is poor Tony.
We don't know Tony all that well before he flees, but he seems like a perfectly nice
person. However, Michael decides to make Tony's weight into a big issue, the same way he focuses
on all of his employees' quirks or insecurities for comedy value. Hoping to welcome the new
employees to his branch, Michael encourages them all to climb on top of a table so they
can be admired by everyone else. Of course, Tony is too heavy to get up there, but despite
pleading with Michael to skip this ridiculous ritual, the boss insists, telling Tony,
"Use the momentum of your lower half to hoist yourself up."
Obviously, Tony is frustrated and humiliated, but things reach unbearable levels when Michael
and Dwight grab Tony's legs and try to shove him up onto the table. It's all too much,
and Tony quits right then and there, telling Michael that his management style isn't so
great after all. Needless to say, Michael doesn't take this very well and fires his
new employee. It's impossible not to feel bad for Tony after he's had to deal with Michael's
frankly offensive weight jabs.
Michael Scott always has to be the center of attention, even at someone else's wedding.
So when bride-to-be Phyllis asks Michael to push her father down in the aisle in a wheelchair,
the boss sees it as his time to shine. However, about halfway to the altar, the old guy decides
to get up and walk. It's a miraculous moment, and while everyone in the church is elated,
Michael is left in the lurch, and pretty angry about it. Michael angrily tells the cameraman,
"Me walking Phyllis down the aisle was supposed to be the highlight of the wedding."
Just like a toddler, Michael throws a tantrum by noisily dragging the wheelchair down the
aisle. He then squeezes himself between the groomsmen, determined to be an important part
of the ceremony. And that's when Michael starts calculating how he can steal the show. Right
after Phyllis says "I do," Michael jumps out and loudly announces the two as a couple.
The trouble is, Bob hasn't said "I do" yet, and Michael is forced to slink back in line.
Then during the wedding speeches, Michael steals the mic and gives an impromptu, and
unwelcome, wedding speech, complete with quotes from The Princess Bride, celebrity couple
names, and off-color jokes about poor Phyllis. Sure, Michael accidentally redeems himself
before the night is over, but all these years later, this probably remains the cringiest
wedding in TV history.
Let's give Michael Scott some credit for the nice things he's done. He was a father figure
to Erin. He played paintball with Dwight. He showed up at Pam's art show and bought
one of her paintings. But all of these wonderful things are canceled out by what happened in
the show's sixth season, during The Office's most painfully cringey episode, "Scott's Tots."
Years ago, Michael Scott fell in love with a group of low-income elementary students.
Figuring he'd be a millionaire by the time the kids were ready to graduate, Michael promised
he'd pay their college tuition. But when it comes time to shell out, Michael is still
just a middling regional manager who once tried to hop on a train because his finances
got so bad. So when he's forced to visit the school to meet the now grown-up kids, adorably
known as "Scott's Tots," the tension is absolutely unbearable.
"I want people to be afraid of how much they love me."
When Michael shows up at the school, the kids absolutely adore him. They give speeches thanking
him for changing their lives, and they even put on a song-and-dance number to show him
their gratitude. By the time they're done performing, a guilty and terrified Michael
gets up in front of the class, and reveals he can't pay for anything. Instead, he bought
them all laptop batteries to make up for his major mistake. Needless to say, this does
not go over well with Scott's Tots. Michael Scott might have good intentions, but the
size of his heart doesn't match the size of his brain.
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