Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
Weird
Everyone can relate to the maddening helplessness of having to endure the antics of someone like Michael Scott. From 2005-2011, the self-proclaimed “World’s Best Boss” drove the employees of Dunder Mifflin bonkers on NBC’s hit comedy The Office. But despite his many faults and the seemingly endless amount of bad ideas and ill-conceived shenanigans, Steve Carell’s undeniable charisma transformed this cringe-worthy buffoon into one of the funniest and surprisingly most-endearing characters in sitcom history.
From his tender friendship with Pam to his unbridled hatred for Toby “everything that’s wrong with the paper industry” Flenderson, Michael Scott’s unique combination of insecurity and unrelenting desire for friendship led to some of the funniest and most emotional scenes on television. In a lesser actor’s hands, Michael Scott could have been a disaster, but Steve Carell imbued the role with so much earnestness that the character blossomed into a beloved television staple.
Cobbling Michael Scott’s greatest moments down to ten episodes is daunting when you consider his seven season run. It truly seemed like an impossible task until I remembered this nugget of sage advice from Wayne Gretzky/Michael Scott: “Remember, you miss 100% of the shots you don’t take.”
Two weeks ago we celebrated the very best of Jim “Big Tuna” Halpert. Today, we revisit the 10 best Michael Scott episodes of The Office.
'The Dundies' (Season 2, Episode 1)
The abbreviated first season of The Office had some solid episodes, but the Season 2 premiere, “The Dundies,” was the first truly great offering from this classic sitcom. Not only do you have Michael’s trainwreck performance as the master of ceremonies, but we also catch our first glimpse of the Dunder Mifflin employees coming together to embrace the absurd charms of Michael Gary Scott.
“Was this year’s Dundies a success? Well, let me see. I made Pam laugh so hard that she fell out of her chair and she almost broke her neck. So I killed, almost.”
'The Client' (Season 2, Episode 7)
“The Client” is an important episode of The Office. It’s here we learn that despite his grating personal behavior and myriad shortcomings as a boss, Michael Scott was at one time an exceptional salesman. Not only does that help to answer the question of how he got promoted to regional manager, but we also see the beginning of the wonderful, insane romantic relationship between Michael and Jan.
Tim Meadows is predictably terrific and we’re also treated to the tour de force known as Threat Level Midnight.
'The Injury' (Season 2, Episode 12)
“The Injury” did more for the George Foreman Grill than George Foreman. Okay, not really. But maybe?
I wish I could’ve been there when the writing staff came up with the idea of Michael burning his foot on the grill. It’s so simple yet so freaking funny. Michael’s severe overreaction to his “injury” drives the humor, but Dwight’s Flowers for Algernon-inspired concussion storyline is the perfect complementary plot. His “You can’t fire me; I don’t work in this van!” quip is another prime example of A++ comedy.
Ryan: “No, the gas station in Carbondale did not have fresh yams!”
'The Convict' (Season 3, Episode 9)
The gang from Dunder Mifflin are used to Michael’s capers, so it’s fun to watch the erstwhile Stamford crew react to Mr. Scott when he’s dialed up to ten.
Written by Ricky Gervais and Stephen Merchant (who created the original British version of the series), the branch learns that Martin was once incarcerated for insider trading. When Pam jokes that prison sounds better than Dunder Mifflin, Michael (obviously) overreacts and “Prison Mike” is born.
Michael Scott: I stole and I robbed and I kidnapped the President’s son and held him for ransom.
Jim Halpert: That is quite the rap sheet, Prison Mike.
Michael Scott: And I never got caught, neither.
Jim Halpert: Well, you were in prison, but… Mm-hmm.
'A Benihana Christmas' (Season 3, Episode 10)
Directed by Harold Ramis, “A Benihana Christmas” is the perfect followup to Season 2’s exceptional holiday episode, “Christmas Party.” After being dumped by Carol for photoshopping himself into a family vacation photo (naturally), a distraught Michael takes a trip to Benihana with his entourage (Jim, Dwight, and Andy. Oh yeah!).
Michael and Andy meet two waitresses and bring them back to the office party, but Michael is unable to tell them apart so he marks one of them with a sharpie… as one does. Dumped for the second time in eight hours, Michael asks a mystery woman (Jan) to accompany him on a vacation to Jamaica.
Bonus goodies: Kevin’s surprisingly passionate performance of “You Oughta Know” and Kelly’s personalized version of Pat Benatar’s “We Belong.”
“We belong, we belong, we belong together, Ryan.”
'Dinner Party' (Season 4, Episode 9)
Listen, babe. This Office episode is one of the top-to-bottom funniest of the series, babe. A peek behind the curtain at the tornado of insanity that is Michael’s relationship, “Dinner Party” highlights the increasingly dysfunctional romance between Jan and Michael.
Imagine the worst dinner party you’ve ever attended, multiply that by 100, and then add Serenity by Jan, a candle-making business you can co-own for only $10,000. This episode is pure mayhem as the humor brilliantly heightens until, eventually, Jan throws one of Michael’s Dundies through his tiny plasma TV.
“Honey, I have the best trophy right here… aside from my Dundies.”
'Goodbye, Toby' (Season 4 Episode 14)
Michael’s unrelenting antipathy towards Toby is my favorite thing. Not just on The Office but on planet Earth.
In the Season 4 finale we (briefly) bid farewell to our favorite HR rep while also meeting Michael Scott’s future wife, Holly Flax (Amy Ryan). “Goodbye, Toby” is littered with fantastic moments: Michael’s giddiness at the beginning of Toby’s final day, his not so subtle “I’ll kill you” during their exit interview, the “Goodbye, Toby” song, and the sad revelation that Jan artificially inseminated herself while dating Michael.
The episode did a wonderful job of introducing the character of Holly while also setting up a ton of stories for Season 5. Also, this isn’t from the episode, but this quote brings me so much joy.
“Why are you the way that you are? Honestly, every time I try to do something fun or exciting, you make it not that way. I hate so much about the things that you choose to be.”
'Broke' (Season 5, Episode 25)
Despite the title, this is not the episode of The Office in which Michael Scott dramatically declares bankruptcy.
Directed by Steve Carell, “Broke” was the conclusion of the enjoyable Michael Scott Paper Company arc. Michael once again demonstrates that there’s a method to his madness as he proves to be a shrewd businessman while negotiating a return to Dunder Mifflin for Pam, Ryan, and himself.
“There are certain defining moments in a person’s life. The day he is born. The day he grows hair. The day he starts a business. And the day he sells that business back to Dunder Mifflin.”
'Garage Sale' (Season 7, Episode 19)
“Garage Sale” is known for Michael’s adorable proposal to Holly, but it’s the assortment of small moments that make The Office such a beloved classic.
Pam calls Michael into a meeting he didn’t schedule, so to cover he just starts talking about recycling. It’s a tiny moment, but it’s perfectly in character with the Michael Scott we’ve grown to love. Little beats like this separate good shows from memorable, rewatchable fan favorites.
Michael’s proposal was silly, emotional, and it set off the fire alarm. The Office trifecta.
'Goodbye, Michael' (Season 7, Episode 22)
The final goodbye between Michael Scott and Jim Halpert will bring a tear to your eye.
Even though it’s a happy ending — Michael is moving to Colorado with Holly — you can’t help but feel as though it’s the end of an era. As Jim and Michael part ways, the genuine sense of friendship and respect between John Krasinski and Steve Carell shines through.
Saying goodbye to Michael Scott was hard but satisfying.
That’s what she said.
You can watch Michael and Jim’s tearful farewell scene here.
