Michael Scott did some pretty cringe-worthy things in The Office that he likely wouldn't get away with were the show airing in today's climate. It's true that Michael was inappropriate on numerous occasions but what makes him forgivable is that he always meant well.
Michael's heart is usually in the right place, so while his execution of things may be poor much of the time, the audience still ends up rooting for him. His wins are the audience wins; the same with his losses, and his huge swings and misses. Michael grows on fans in the way that only an underdog can. Whether it's in trying to win Holly back or being taken more seriously within the company, the audience wants Michael to succeed.
When He Started His Own Paper Company
When Michael Scott quits Dunder Mifflin with his iconic line, "You have no idea how high I can fly," it's both funny and inspiring. Though he may spend lots of time disrupting the office workday with his distractions and procrastinations, he still manages one of the company's most successful branches.
Though The Michael Scott Paper Company was eventually reabsorbed into Dunder Mifflin, during its brief run, fans wanted it to succeed. It was such a big move for Michael to step out on his own because for a large chunk of his life Dunder Mifflin has been all he's known.
"Where Are The Turtles!?"
Michael yells this to a client after demanding back his gracious gift basket. Michael sets out to prove a point to Ryan, that the old ways of customer service are not dead and gone. This definitely appeals to viewers of a more traditional camp and they hope Michael can succeed. It's also a good opportunity for Michael to stick it to Ryan, an acclaimed "wunderkind."
Fans wanted him to succeed on his gift-basket-bearing quest to prove to Ryan that technology isn't everything. Unfortunately, viewers know how it ends--with Michael's car submerged in a lake.
His Golden Ticket Idea
In season 5, Michael hides golden tickets in random deliveries in the warehouse as a new sales initiative. He even dresses up as Willy Wonka, bouncing around the office with a cane and a top hat.
Even though Michael first pins it all on Dwight when he realizes his brilliant idea might go south, fans want Michael to get the credit he deserves when it turns out Blue Cross of Pennsylvania makes Dunder Mifflin their sole provider of office supplies. It's almost heartbreaking to watch Dwight stand up in front of the whole office and get congratulated by David Wallace. Though handled poorly, when Michael finally speaks up, it's somewhat of a relief.
When He Fell Into A Koi Pond
After falling into a koi pond at a business meeting, Michael is plummeted with pun after pun. It's sad to watch as he tries his best to take it, but more than likely wants to crawl under a rock out of embarrassment.
Learning that Jim let him fall in is such a win for both Michael and the audience. It comes as such a fun plot twist because Michael comes out on top for a change and Jim is suddenly "the bad guy" and the butt of the joke, reminding fans that things change pretty quickly around the office.
After His Infamous Roast
When Michael decides to let everyone roast him as a way to relieve office stress, it quickly backfires. He receives dig after dig and viewers watch his ego slowly deflate until it altogether drives him out of the warehouse and even skips work the next morning.
During the roast, viewers experience one of those second-hand embarrassments The Office is so well known for. Fans know Michael cannot handle this much criticism the way he thought he did. There's a bit of dark humor watching him sit on the world's saddest park swing and throw bread to birds that aren't there, but nonetheless, the audience feels for him. Later in the episode, he comes back in full swing with a list of roasts for each employee.
His Hopeless Romantic Side
At the end of season 5, Michael surprises everyone when he decides to not meddle for once and let Holly go. He believes that they are just one of those couples with a long story when people ask how they found each other. The audience wants Holly for Michael just as badly as he wants her. Who else is going to match his dorky, wacky sense of humor? It's a sweet touch that he chooses to let time decide what happens to them.
It's a good call back to season 2 when on the booze cruise he tells Jim to never ever ever give up on Pam. Michael's hopeless romantic side gets him in trouble a lot, but his moments of real self-reflection and selflessness when it comes to matters of the heart can't go unmentioned.
"There's Been A Murder...In Savannah"
In season 6, amidst rumors of Dunder Mifflin going bankrupt, Michael has everyone in the office participate in a murder-mystery game to preoccupy their worries. He even gets short and assertive with Jim when he tries to shut it down. "They need this game, Jim! Let us have this stupid little game, alright?"
It's a sweet gesture and Michael comes across as a protective parent trying to distract his children from possible devastating news. Michael shows time and time again just how empathetic he can be and it's in these moments fans root for him most.
The Film He's Worked On For Ten Years
Knowing Michael very well at this point, fans had a sense Threat Level Midnight wouldn't be a knockout--he is a paper salesman by trade--but they wanted it to be good for him. Michael is so proud and he worked so hard. When Holly isn't into it he's disheartened and shuts the movie off.
This was another moment fans rooted for him because it shows his giant heart. To him, making this movie was another way to hang out with everyone at the office outside of the workplace. He sees his co-workers as more like friends and family and that's indicative in everyone's inclusion in his homemade movie.
Cafe Disco
When Michael says goodbye to his small office downstairs that made up The Michael Scott Paper Company, he can't just say goodbye casually. Like with most situations, he tries to turn it into a party. At first, no one will bite and viewers watch as he dances and sips espresso all by himself.
But who didn't want to attend "cafe disco?" At the very least, it serves as a nice reprieve from the workday. Michael likes to see the bright side of everything and it's one of his most likable qualities. Perhaps Michael should win the Dundie for World's Best Morale Booster.
His Commercial
In season 4, Dunder Mifflin is asked to do a local commercial and Michael takes this opportunity and sprints. He takes it even more seriously than the production team that was hired.
Fans are just as bummed as Michael when they end up running the stock ad instead of his, especially with how great it actually turns out. This was one of those moments that showed Michael's true heart in that he really thinks of his employees as family and relishes in their moments together.