watchworthy presents

The Saddest Moments On 'The Office' 

Rory Arnold
Updated February 7, 2020 504 votes 93 voters 1.5k views 14 items

List Rules Vote up 'The Office' moments that bring a tear to your eye.

There are so many moments from The Office that have stood the test of time and remain funny years later and after much repetition. Michael hitting Meredith with his car may be one of the greatest comedy television moments from the early 2000s, and his trainwreck dinner party with Jan serves up all of the belly laughs.

But, given its documentary-style format that catches a range of emotions, the beloved series is also known for its sincere and heartfelt moments like Jim and Pam’s wedding and Michael’s tearful goodbye. In spite of all the silliness, there are times when the characters on The Office endure real pain and crushing heartbreak. Here’s a rundown of some of the saddest moments in the history of The Office - and be sure to vote up the ones that truly tug at your heartstrings.

Data-driven recommendations based on voting from over 40 million monthly visits to Ranker. Try the free app
Michael Leaves Dunder Mifflin A Day Early
Michael Leaves Dunder Mi... is listed (or ranked) 1 on the list The Saddest Moments On 'The Office'
Photo: NBC

Episode: Goodbye, Michael (Season 7, episode 22)

Why It's Sad: When Michael announced his departure from Dunder Mifflin, it was difficult to imagine The Office without him. In "Goodbye Michael," everyone believes this is Michael's penultimate day at the office, when it is in fact his very last. To say goodbye, he plans to share a special moment with each of his staff members - offering them advice or giving them physical gifts like a silly painting for Kevin, his clients for Andy, and a letter of recommendation for Dwight. Jim cracks this code, though, and when he confronts Michael about when he's actually leaving for Colorado, they share a touching moment about working together for the past several years, exchanging heartfelt compliments. Antics aside, Michael means so much to The Office and it's heartbreaking to watch him leave. 

Barely Anyone Shows Up To Pam’s Art Show
Barely Anyone Shows Up T... is listed (or ranked) 2 on the list The Saddest Moments On 'The Office'
Photo: NBC

Episode: Business School (Season 3, episode 17)

Why It's Sad: In “Business School,” Pam is back with Roy and having an art show at her school. Pam invites everyone at the office to attend, and while Kelly pretends to be excited and Toby is genuinely, perhaps excessively, disappointed that he has to attend his daughter’s school play that night instead, hardly anyone shows up to support her. At the show, Pam overhears Oscar and his boyfriend Gil criticize her art, with Gil describing it as “motel art.” They quickly leave without realizing Pam overheard them. When Roy shows up, he rubs salt in her wounds be pointing out that nobody else from Dunder Mifflin attended. Pam is left bummed out and disappointed that her friends couldn’t be bothered to drop by and support her true passion. Michael eventually shows up and Pam is extremely grateful, but the art show as a whole is incredibly hard to watch.

Pam Turns Jim Down After Casino Night
Pam Turns Jim Down After... is listed (or ranked) 3 on the list The Saddest Moments On 'The Office'
Photo: NBC

Episode: Casino Night (Season 2, episode 22)

Why It's Sad: In the Season 2 finale, it’s Casino Night at the Dunder Mifflin warehouse and Jim and Pam’s friendship is about to hit a major crossroads. After much debate, and watching Pam and Roy go from failing engagement to an actual wedding date, Jim talks to Jan about a transfer to the Stamford branch. Before officially accepting the new position, Jim takes a chance and tells Pam how he truly feels about her. Just when it feels like it might be the moment everyone’s been waiting for and that the budding romance will finally take off, Pam tells Jim she can’t be with him and is sorry he misinterpreted their friendship. Jim apologizes and, in a truly soul-crushing moment, quickly wipes a tear from his face and leaves. He does come back and kisses her just to see how it felt, but is again turned down for Roy. 

The Staff Sings To Michael After His Final Dundies
The Staff Sings To Micha... is listed (or ranked) 4 on the list The Saddest Moments On 'The Office'
Photo: NBC

Episode: Michael's Last Dundies (Season 7, episode 21)

Why It's Sad: The Dundies are an awards ceremony that Michael puts together to recognize the members of Dunder Mifflin annually for their accomplishments. Most of the awards are just silly, like the Spiciest Curry award he gives to Kelly or the Whitest Sneaker award he gives to Pam after years of giving her The World's Longest Engagement award. Many of the staff members even confess to not enjoying the ceremony at all, but putting up with it because it means something to Michael. Just before Michael leaves to be with Holly in Colorado, they host his final Dundies.

It doesn't quite go to plan and they get kicked out of their restaurant venue, but before everyone goes home, they gather in the conference room and sing a parody of Rent's "Seasons of Love." In the lyrics they put some of the most memorable Michael moments, like running over Meredith and kissing Oscar, and while the references are funny, the sentiment is entirely heartfelt. Imagining the office without Michael is clearly tough for the employees and it's hard not to tear up hearing a recap of all of their moments together.