Known for his buffoonery and countless moments of awkwardness, Michael Scott is simultaneously the funniest and endearing character on The Office, who constantly exclaims many unintentionally problematic comments. However, we can’t help but love the self-proclaimed “world’s best boss”, faults and all.
Some of the funniest moments in the show involve Michael Scott in some form or another. Whether he’s spouting out “That’s what she said”, having an argument with Jan at the world’s most cringe-worthy dinner party, or, let’s not forget, his many personas. While Michael has delivered many uproarious moments, it’s his more endearing moments that make fans inherently connect with him, humanizing the very immature boss. So polish your Dundies, as we rank Michael Scott’s most endearing moments.
8 Making Sure Pam and Ryan Keep Their Jobs
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After leaving Dunder Mifflin due to Idris Elba’s Charles Miner, Michael left to start his own paper company, The Michael Scott Paper Company. Inventive, right? Well, during his dramatic exit, Pam decided to leave as well and join Michael on his ventures. Looking to increase the staff, Michael hired Ryan to join his rag-tag group of salesmen.
Later in this season five arc, The Michael Scott Paper Company steals the majority of Dunder Mifflin’s clients, to which David Wallace, Charles Miner, and Jim Halpert call a meeting to buy out Michael’s paper company. Michael turns down any buy-out, however, and instead, demands Pam, Ryan, and himself get re-hired by Dunder Mifflin. Michael often proves how much he cares for others, but to turn down $60,000 dollars, so his two loyal friends can get their jobs back, is one of Michael’s most selfless moments.
7 Paint Balling with Dwight
Oftentimes throughout the show, Dwight proves how much Michael means to him and constantly asks Michael to go paint balling. Likewise, Michael doesn’t often show Dwight the same respect or love, constantly calling him an idiot. However, deep down, Dwight, the assistant to the regional manager, means so much more to Michael than he lets on, which is showcased in season seven before Michael’s departure, when Michael surprises Dwight with a paintball fight.
6 Handing Out Candy to Trick or Treaters
Prior to this moment, fans never really saw a sympathetic or generous side to Michael, that made us utterly adore his character. This moment in season two gave Michael the layers and heart for his character to be more than just an embarrassing boss. After a sad Halloween, Michael was forced to fire an employee, which was kind of his own fault for putting it off for so long. However, when firing Devon doesn’t go exactly the way Michael thought, with Devon storming out and throwing a pumpkin at Michael’s car, we see Michael at home looking very upset and down, but when a group of trick or treaters arrives, Michael is in his element and joyfully gives out a generous amount of candies to the kids at his door.
5 Jim and Michael’s Goodbye
It goes without saying, but Michael Scott’s departure was filled with emotions, from the characters, fans, and of course, the cast. But no moment was as gut-punching as Jim’s goodbye to Michael. While John Krasinksi (Jim Halpert) and Steve Carell (Michael Scott) are brilliant actors, their true emotions shined through this scene, as both actors try so hard to keep it together, yet tears immediately fill their eyes, adding an authenticity to the scene that never fails to leave us in emotional wrecks.
4 Dwight’s Wedding
Dwight’s wedding to his beloved Angela is one of the most important moments in the show, and of course, the most important day for Dwight. There is no one Dwight would rather have at his wedding than his former boss and best friend, Michael Scott. Two seasons after Michael’s tear-jerking departure, fans hoped for but never really expected Steve Carrell to return as Michael Scott. Thankfully, fans were pleasantly surprised when Michael made the only entrance he knew how, with his first words being “that’s what she said”.
3 Proposing to Holly
Throughout the show, Michael has had many love interests, including his real estate agent, Carol Stills, Pam’s mother Helene, and of course, Jan Levinson. But Michael has never loved anyone as much as Holly Flax, the literal female version of Michael Scott. Both put on weird voices and impressions, as well as some questionable humor that only the two of them found funny, in many uncomfortable yet cute moments between the pair.
One of the most tragic moments in the show was when Michael and Holly split up and went their separate ways, but thankfully they both reunited in an adorable twist of fate. Holly’s return leads to Michael inevitably proposing to her in perhaps the most romantic proposal on TV, filled with hundreds of candles and a shower from the building’s sprinkler system. As adorable as this moment is, it ends with Michael telling the office he is leaving, in a one-two emotional punch.
2 Michael Gives Jim Advice on Pam
The romantic arc between Jim and Pam spanned a full three seasons, with many will-they-won’t-they moments, but if it wasn’t for Michael’s advice on the booze cruise, they may have not ended up together at all. At the end of the booze cruise, Jim and Michael have a heart-to-heart, with Jim admitting his feelings for Pam. Jim, however, never expected Michael’s advice to be kind of great, who tells Jim to “never give up”. After Jim disappointingly says “she’s [Pam] engaged”, Michael fires back with “BFD, engaged ain’t married”, to which Jim takes on board, leading to Jim and Pam’s kiss on Casino Night at the end of the second season.
1 Buying Pam’s Art
Pam has always aspired to be an artist; a career which no one has ever really supported but Jim. When putting on an art show, no one else shows up but Oscar and his partner Gill, who heavily criticize her work, and Roy, who shows up with his brother, but they both swiftly leave without appreciating her inspiring artwork. Pam is understandably disappointed and saddened that no one turned up, and those who did, tear down her confidence. But it’s Michael’s last-minute appearance that makes Pam and her artwork feel appreciated, with Michael buying one of Pam’s drawings (which was a shock and adds a ton of heart, as they weren’t for sale) and hangs it in the office. Michael really knows how to make his best friends feel special and cared for.
