Summary

• Michael Scott evolves from clueless boss to kind and endearing figure as shown in various touching moments.
• His acts of generosity, mentorship, and emotional vulnerability reveal his true heart despite his flaws.
• By providing and creating special memories, Michael demonstrates his genuine care and love for his friends and colleagues.

Michael Scott may be one of the quirkiest characters on TV, but he also has several moments in The Office that show a surprisingly sweet and kind side to him. The Office was a popular comedy show that aired from 2005 to 2013, with a total of nine seasons. The show was originally adapted from a British comedy show of the same name by comedian Ricky Gervais, though after the first two seasons, The US Office far sured the original in of viewership and popularity.

The strength of the series relies on the incredible cast that includes actors that have moved on to establish themselves as some of the most popular actors in Hollywood, including John Krasinski and Steve Carell. While Carell's character, Michael Scott, initially resembled his British counterpart, David Brent, played by Gervais, the character showed some clear differences early on that made him extremely endearing and sweet, despite his many flaws.

10 Candy For The Trick Or Treaters

The Office Season 2, Episode 5

In the first season of The Office, Michael Scott proved to be an extremely incompetent and frustrating boss. Though he tended to be on the sillier and quirkier side than his inspiration, David Brent, nonetheless, he wasn't characteristically charming. This all changed in season 2 as the character proved to be more layered and gave viewers reasons to connect with him.

One of the earliest moments that stands out as a change in the character and shows off his more lovable side is during the second season, when he is going through a rough spot after firing one of the employees. Michael struggles with conflict and not being liked, so firing someone is extremely challenging for the character. However, that evening, when he is home alone, he is able to get energy and joy by celebrating Halloween and the young kids that visit his door when he praises their costumes and gives out candy in generous handfuls.

9 Caring For Toby's Daughter Sasha

The Office Season 2, Episode 18

Later in the same season, Michael has another moment where he connects with one of the children visiting the office. He is unsure who in the office the child belongs to, but when the young girl, Sasha, comes to his office, he puts his work aside and chooses to give her attention. He shows off his toys and knick-knacks and the pair become fast friends.

Michael is, in many ways, childlike, playful, and full of awe and wonder. This may potentially explain why he finds it easier to connect with kids who find joy and excitement in small things, rather than the adults who find his personality tiresome. However, what adds to the beauty of this moment is the fact that this is Toby's daughter, Michael's sworn enemy in the office. Putting their differences aside, Michael is just happy to show kindness to young Sasha, helping her to have a positive memory at the office while her father somehow misplaced her due to prioritizing his work.

8 Being A Father Figure To Erin

The Office Season 7, Episode 8

Michael also dreams of being a father himself, which he mentions multiple times throughout the series. However, this doesn't happen for him until much later, when he's already left the show as a main character to pursue a relationship with his girlfriend, Holly Flax. Despite this, Michael does end up having a special parental bond with one girl in the office, Erin.

Erin is a unique character, who views Michael as a father figure in her life whom she has enormous respect and affection for. Michael initially fails to recognize how deep these feelings are for Erin, but, he begins to understand much better in season 7, when Erin seeks his approval when dating Gabe. Michael initially upsets Erin, but when he realizes what is happening, he makes a big gesture to apologize, and assumes that fatherly role that she craves from him. After this moment, Michael continues to and advise Erin, strengthening their bond.

7 Letter of Recommendation For Dwight

The Office Season 7, Episode 21

As Michael makes preparations to leave Dunder Mifflin for good, he sets to work on doing something for each of his dear colleagues and friends. Michael and Dwight have had a rollercoaster relationship throughout the series, but, in his final interaction with Dwight before leaving, he provides him with a letter of recommendation. Dwight is skeptical, because Dwight has never been particularly affectionate or kind to him. However, the contents of the letter are glowing and all that Dwight could hope for.

Not only does Michael give him the recognition and highest praise he can give, but he also has a surprise for his friend that requires him to follow cryptic instructions on a card. This, of course, excites Dwight, and he rushes to follow the instructions. What follows is a beautiful moment in the car park where Michael and Dwight play paintball.

6 Pam's Art Gallery

The Office Season 3, Episode 17

Much earlier, in The Office season 3, Pam finds herself struggling to find and pursue the things she really wants in life. She has a ion for art, but failed to pursue it for years due to her work at Dunder Mifflin as a receptionist, and her dead-end relationship with a coworker, Roy. However, when she gets an opportunity to display her work at a local gallery, she invites all of her coworkers to come and her.

Heartbreakingly, no one shows up, until just as Pam loses hope and is preparing to take down her drawings, Michael rushes in out of breath. He reveals that he has been rushing to get there and was stuck in traffic, but when he arrives, he couldn't be more complimentary of Pam's art. After receiving almost no attention, Michael's praise, and his declaration of "I am really proud of you," cause Pam to hug him. Michael sincerely loves her art, and wants to buy her drawing of their office building, which gives Pam the validation she needs to keep pursuing her dreams.

5 A Moment Of True Vulnerability With Jim

The Office Season 5, Episode 11

Krasinski's Jim Halpert is one of the most competent and intelligent characters on the show, and this is seen throughout when he is offered promotions and opportunities to advance. In the absence of Michael, he is often placed as an interim manager or leader, ing and guiding the team. However, for all Jim's intelligence and charm, there are parts of managing that still stump him.

When a fight breaks out with the party planning committee, and Jim's best efforts to help fail to improve the situation, Michael sits with Jim and recounts some of the mistakes he made early in his management career. At first, Jim ignores it, but Michael offers a rare look beneath the surface level kookiness, explaining why he sometimes makes dumb jokes to defuse tension. The pair bond and connect over their shared struggles.

4 Saying Goodbye To Jim

The Office Season 7, Episode 21

Later, with Jim in season 7, the pair again share another touching moment as Michael prepares to leave Dunder Mifflin for good. While everyone knows Michael is leaving, he struggles with the idea of saying goodbye to friends that have shaped his life for so many years. So, instead, he plans to sneak away, a day ahead of when he is intended to leave to avoid the emotional goodbye.

However, Jim knows Michael well, and when he sees Michael anxiously pushing to check off his list of things to do before leaving, he figures out what Michael is planning. He walks into his office, closing the door behind him and has his suspicions confirmed, and in an effort to honor Michael's wishes, they don't speak it out loud. However, the goodbye they share is an intense and beautiful emotional moment with both on the verge of tears.

3 Michael Proposing To Holly

The Office Season 7, Episode 19

Just prior to leaving in season 7, Michael establishes the reason he has to leave his job and the people he has formed such an intense connection with. Earlier in the series, Michael had formed a close relationship with Holly Flax, an HR rep. The pair were perfect for each other, with similar quirks and senses of humor, and they fell madly in love. However, it appeared that fate was against them when the pair were forced to work far apart.

They tried long distance, but it failed quickly, and then Holly found new love and got engaged. This broke Michael's heart, so when the opportunity came back to work with Holly, who had recently broken up with her former fiancé, Michael didn't waste a second. His proposal to Holly, surrounded by candles, was incredibly touching and emotional, and a rare moment of vulnerability from the character.

2 Saving Ryan And Pam's Jobs

The Office Season 5, Episode 25

In The Office season 5, Michael decides to part ways with Dunder Mifflin when he becomes disillusioned with how they do business. He sets up his own paper sales company, and poaches some of the other employees and ex-employees from the company, namely Ryan and Pam. Initially, the new company gets off to a great start, but due to a lack of funds and forward planning, they begin to rapidly lose money.

Michael needs to do something drastic to ensure that he hasn't destroyed his life and the life of the people he convinced to work with him, and he ends up setting up a meeting with David Wallace of Dunder Mifflin to discuss them buying his new startup. DM makes a pitiful offer, and Michael shows off his exceptional, though rarely seen, business skills by negotiating a far better deal, and securing jobs for Ryan and Pam. This once again shows how much he cares about and for his friends, and the lengths he goes to protect and help them.

1 Dwight's Wedding

The Office Season 9, Episode 23

Finally, the last surprising moment where Michael Scott makes a big impression in The Office comes in the series finale. After leaving the show and being absent for the last two seasons, Michael Scott makes a surprise return at Dwight's wedding. Jim has acted in the role of best man for Dwight, since their relationship has grown steadily over the series, but he hasn't given up his pranking habits.

When Dwight expects to see Jim as he approaches the altar where he will soon be married, Jim has coordinated to have Michael appear and surprise Dwight as his best man in Jim's place. This is a huge moment for Dwight and the rest of the guests who have relationships with Michael. The moment is beautiful, and seeing Michael Scott return to The Office, happy and fulfilled, is the perfect send-off to one of the most beloved shows on TV.