The Office: 10 Saddest Moments, Ranked

The Office (US) is one of the most beloved television comedies of all time. The misadventures of the folks at Dunder Mifflin never fail to put a smile on our faces and provides the occasional touching moment. While the show is no doubt hilarious, it also had a real talent for tugging at the heartstrings of its audience.

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After nine seasons, we came to love all these wacky characters. Despite their very evident flaws, we wanted to see them happy and were heartbroken when things didn't work out for them. The relationships we cared about had problems which meant the tears of laughter were occasionally replaced with tears of sadness. Here are the saddest moments ever on The Office.

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10 Kevin's Chili

It's a real skill to create one of the funniest moments in the show's history which is also one of the most heartbreaking. In this classic cold open, Kevin Malone excitedly talks about his famous chili which he makes once a year for the office. As he is detailing the painstaking work that goes into this and his passion for the cooking, we watch as Kevin struggles with the massive pot and dumps it all over the office floor.

It's impossible not to laugh at the moment, but it's also impossible not to feel bad for Kevin. The devastation on his face is so painful as he talks about how this is the thing he is most talented at. His pathetic attempts to clean up the mess only makes it worse.

9 Erin's Father Figure

Erin in The Office

Erin Hannon is one of the most happy-go-lucky characters on the show. She is kind and warm to everyone, while also be a little oblivious. But she also has a pretty sad past in which she was a foster child who had trouble finding a permanent home. Since her childhood, she has been searching for a parental relationship.

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Erin immediately takes a liking to Michael, looking at him as her surrogate father. Sadly, Michael doesn't understand how important he is to Erin. When she seeks his respect and approval, he dismisses her, breaking her heart. Luckily, Michael then understands what she's looking for and gives her the faux-fatherly advice she was seeking.

8 Closing Ceremonies

The Office Michael Scott Jim Dwight Office Olympics Awards

The Office Olympics were another classic plan that Jim came up with to avoid having to work. He gets the entire office excited for the creative office-based games while Michael is out for the day. While the rest of Dunder Mifflin is having fun, Michael is in the midst of buying a condo which he quickly realizes has a terrible investment.

When Michael returns to the office after having a horrible day, the games immediately come to a stop. However, Jim wants to see the thing through and recognizes his boss needs some cheering up. With tears in his eye, Michael receives his gold medal and quickly forgets all his problems.

7 Pam Breaks Down

The Office Pam Brian Console

The final season of The Office was disappointing to many fans of the show. The absence of Michael Scott was really being felt in the last episodes, and the show didn't feel like itself anymore. The final season also had a storyline which troubled many fans as Jim and Pam's perfect relationship began to fall apart.

With Jim in Philadelphia, trying to start a new business, the distance put a strain on things. After one particularly heated conversation over the phone, Pam breaks down in tears and is comforted by a member of the documentary crew. It's devastating to see poor sweet Pam trying so hard but seeing her marriage in serious trouble.

6 Pam Confronts Jim

The relationship between Jim and Pam has had a lot of ups and down over the years, which we'll see throughout this list. For so long, this seemingly ideal couple just couldn't seem to line things up to make it work.

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After Jim left Scranton, he eventually returned but with a girlfriend. This destroyed Pam's chances of finally being with him and led to a season of her dealing with that sadness and becoming a more confident person. This led to Pam confronting everyone at Beach Day, including Jim who she felt she had lost as a friend. It's a difficult moment to see Pam put her heart out there finally and address her pain.

5 Michael And Holly Break Up

While Jim and Pam are clearly everyone's favorite romance from The Office, there's no denying that Michael and Holly were adorable together. It seemed impossible that Michael would ever find a perfect match but Holly certainly fit that bill. However, they also had a bit of a rocky road to romance.

When corporate finds out that Michael and Holly are an item, they decide to transfer Holly to another office. They convince themselves that they can make the long distance work, but when driving Holly to her new life, she has a breakdown, realizing it's not going to work. As insensitive as Michael can be, watching his one shot at happiness be taken away was pretty rough.

4 Jim Confronts Pam

Before Pam told Jim how she felt, he was the first to bare his heart for her. At the office Casino Night, Jim finally says what we had been waiting two seasons to hear him say — he loves Pam. This, of course, puts Pam in a very difficult position since she is engaged.

Ultimately, Pam rejects Jim and you can immediately see how much that hurts him. He knows how she feels about him but there's nothing left he can do. The goofy prankster side of Jim we're sued to disappears and we're left feeling sorry for a guy with a broken heart.

3 Pam's Art Show

Jim and Pam in The Office

Pam's love of art has always been a big part of her character. Jim has usually been the only person to encourage her in her pursuit of that, but she slowly started to get more confidence in her skills. She even enrolled in an art class and had her work displayed in an actual art show.

Despite being very excited and inviting the entire office, no one shows or gives their support — not even Jim. Defeated, Pam is ready to leave when Michael shows up at the last minute. He is enthusiastic and proud of Pam and even offers to buy one of the pieces, causing Pam to hug him and cry.

2 Jim And Dwight Have Heart To Heart

Rainn Wilson and John Krasinski as Dwight and Jim in The Office

Dwight and Jim were the best of enemies for much of the series. They rarely ever saw eye-to-eye and were usually actively hurting each other. But they do eventually find some something they both are familiar with — heartbreak.

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After Dwight's relationship with Angela falls apart, he falls into a depressed state. Jim finds him one day crying in the stairwell and tells him he understands the pain that he is going through and would not wish that on his worst enemy. In a touching and funny moment, Dwight goes in for a hug not realizing Jim already left.

1 Michael Leaves

Michael Scott leaving is the most devastating thing that happened on the show — and that's not just because his exit hurt the show's quality dramatically. While the reasons for leaving to start a new life with Holly were cause for celebration, the goodbye was hard to take.

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Michael tries to avoid the painful farewell by leaving one day before he said he was. He shares a final moment with everyone, but misses Pam who is away from the office. She eventually tracks him down and she sees him off on his way to his new life.

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