The 10 Most Heartbreaking Episodes of ‘The Office,’ Ranked

The Office is one of the most popular sitcoms in the U.S., being an adaption of the British sitcom series by the same name. So much so that Peacock is producing a spinoff of The Office, though it will feature a new cast. Still, there is hope for the return of the original characters who made the show the wholesome and comedic show that it is.

While The Office has had plenty of wholesome moments, it has also had plenty of sad episodes and moments which strengthened and gave foundation to the characters and story. Many of the sad episodes take place later on in the series when viewers have grown to love and appreciate the cast. It’s hard not to shed a tear when these moments play on TV.

10. “Casual Friday” Season 5, Episode 26

Kevin’s Famous Chili

“Casual Friday” is the reinstatement of Dunder Mifflin’s “casual Friday” with Michael (Steve Carell), Pam (Jenna Fischer), and Ryan (B. J. Novak) returning to the company. It opens with Kevin (Brian Baumgartner) bringing in his famous chili to bring everyone closer together again, but as he struggles to get the pot upstairs, having a hard time due to the comedic timing of the elevator being out of order, he spills the entire pot of chili.

This episode does not come close to competing with the other saddest episodes of The Office, but this moment alone is pretty sad in a pitying kind of way. Kevin’s excited voiceover as the crew documents his genuine joy in bringing in his chili despite the hardships that followed, ending with his sincere distress over spilling the entire pot in the office and not being able to scoop it all back into the pot while also getting chili all over himself. This is especially sad when viewers consider that Kevin spent the night slaving over the stove to make everyone his famous chili in hopes of bringing everyone together.

9. “Money” Season 4, Episode 7/8

Dwight Is Rejected by Angela

Due to a financial crisis, Michael begins working a second job as a means of relieving the debt earned while living with Jan. Meanwhile, Dwight (Rainn Wilson) hosts Jim and Pam at his bed and breakfast, where they learn of his anguish over Angela (Angela Kinsey). Later on, Angela publicly accepts Andy’s (Ed Helms) invitation to a date, and Dwight cries to himself in the stairwell, where Jim decides to have a heart-to-heart conversation with him.

Dwight’s infatuation with Angela leads to comedic moments, but when she decides to publicly humiliate Dwight by accepting Andy’s invitation, it’s hard not to feel sad for him. This is especially true when Jim relates to Dwight in their heart-to-heart conversation, speaking of how in love he was with Pam, reigniting old memories. Love is hard, but so is the heartache that comes with it; something that both Jim and Dwight are oh-so familiar with, tragically enough.

8. “Boys and Girls” Season 2, Episode 15

Roy Crushes Pam’s Dreams

Two seminars for men and women in the workplace take place simultaneously at Dunder-Mifflin. However, Michael’s attempts at hosting a seminar backfire when a union is formed, and Jan (Melora Hardin) threatens to close their branch. Later, Jan suggests Pam join a graphic design program, which Roy (David Denman) dismisses heavily. This leaves a crying Pam.

When it comes to love, everyone wants their partner or significant other to support their dreams. It’s not a requirement, but it’s expected to have a supportive partner. Unfortunately, that is not the case when it comes to Roy and Pam, and it is likely that they would never have worked out, even if Jim was not in the picture. Nothing hurts more than to have one’s dreams crushed, especially by someone who is supposed to lift you up. Pam’s tears are very real, and it’ll be hard for viewers to hold in their own tears when watching Pam cry over Roy’s harsh words.

7. “Casino Night” Season 2, Episode 22

Pam Rejects Jim

“Casino Night” is Season 2’s season finale where Michael hosts a charity event inside the warehouse. Jim and Pam discuss a little bit about Pam’s wedding, and Jim decides to confess his feelings for Pam to her. However, things go downhill, as Pam initially does not return Jim’s feelings and rejects him.

Viewers have been rooting for Pam and Jim ever since the start of the show. This is especially true since Roy has proven to be a pretty toxic boyfriend at times, making Pam feel inadequate about herself. However, when Jim confesses his feelings for Pam, she rejects him, claiming that he misinterpreted things. Jim, obviously hurt by her cold rejection, wipes a tear from his cheek. Although it’s pretty clear Pam has feelings for Jim, her cold words strike viewers in the heart; it’s a familiar feeling for many, and it’s one of the worst feelings in the world.

6. “Employee Transfer” Season 5, Episode 6

Michael and Holly Break Up

Michael and Holly’s (Amy Ryan) relationship is discovered, and Holly is in the process of being transferred back to her old branch in Nashua, NH. Darryl (Craig Robinson) and Michael help her on the move back, with the couple planning on working out their relationship via long distance. However, Holly and Michael both realize that it is not going to work out, and Michael joins Darryl on his way back.

Michael has not had the best relationships with women. Rather, he has always struggled immensely when it came to finding someone he could truly love and be with. So, when Michael and Holly first got together, it was like a perfect match (excluding Pam and Jim, of course). When Holly starts to break down into tears while Michael fails at singing “Life Is a Highway,” it’s hard not to feel heartbroken for Michael when it becomes clear that this relationship is not going to last. This is especially the case when Michael realizes that a long-distance relationship could not possibly work, and he has no other choice than to break up with Holly.

5. “Business School” Season 3, Episode 17

Pam Hosts an Art Show

In The Office, Pam often dreams about going to art school. She loves art, and she loves drawing. However, very few people support her dreams, including that of her previous boyfriend, Roy. However, one day, Pam decides to share her art with her colleagues and invites them out to an art show after work. However, no colleagues show up, save for Oscar and his critique-driven partner and her boyfriend at the time, Roy. However, then Michael shows up and purchases a piece of art: a portrait of the Dunder Mifflin building.

Although not the saddest episode, “Business School” was certainly disappointing and gloomy, specifically because of Pam’s art show. Viewers feel for Pam, and it’s hard not to feel sad for someone who tries so hard only to be disappointed. However, this is also a relatable episode, as many have faced a similar disappointment, which can add to the heartbreak that viewers already feel towards a solemn Pam. However, as she begins to pack her paintings up, Michael shows up, and he relishes her art. Most importantly, Michael tells Pam that he is proud of her, a saying that many long to hear, and it’s enough to bring a few tears to the eyes of viewers.

4. “The Finale” Season 9, Episodes 24/25

The End of The Office

“The Finale” is the last episode of The Office. It’s officially a year later after the events at the Dunder-Mifflin office were recorded. The crew reunites to shoot bonus features, and Dwight and Angela are planning their wedding. On the day of the wedding, Michael returns to be Dwight’s best man. Pam and Jim sell their house so that Jim can pursue his dreams, and they inform Dwight of their decision. The cast gives their last round of interviews, and Pam retrieves her old portrait of the office building before leaving.

While many good things happen in this episode, it’s hard not to be a little sad at the conclusion of The Office. Many memories are made with this sitcom, and to see the fitting conclusions of everyone’s story is certainly fitting. Viewers will be elated to see that Pam and Jim are doing extraordinarily well, and they will also be happy to see Michael return. But it’ll be hard not to shed a tear when Pam reviews the painting of the office building that Michael loved and cherished, indicating that an era is leaving, and a new one is beginning.

3. “Paper Airplane” Season 9, Episode 20

Pam Doesn’t Hug Jim Back

After a big fight between Pam and Jim, and with Jim finding out that his actions are pushing Pam away, the two decide to go to couples counseling. They have to do a few exercises throughout the day to remember each other’s appreciation for one another, though they continue to grow more passive-aggressive towards one another. However, as Jim prepares to leave for Philly, he confesses to Pam that he believes in the exercises and that they are beneficial to restoring their relationship. As he leaves, Pam chases after him to return his umbrella to him, and as they stand in silence with one another, he finally caves in and embraces her ever-so-tightly, though she does not return this sentiment. After a long pause, Pam, too, gives in and embraces Jim tightly.

Paired very closely with “Customer Loyalty,” this episode is another tearjerker. Pam and Jim are trying to make amends with one another and fix their strained relationship, but it seems as though the rift between them is too big to fix. This is heartbreaking for the couple’s fans, as viewers have been rooting for Jim and Pam all nine seasons. Things get exceptionally hard and heavy when Pam does not return Jim’s desperate embrace, one that indicates his love for her. It’s a frighteningly sad moment, as Pam seems puzzled about her own feelings, a tough pill to swallow to even consider that Pam is no longer in love with Jim.

2. “Goodbye, Michael” Season 7, Episode 22

Michael Leaves the Office

Michael Scott is the core character that makes the office what it is. Sure, some of his humor can be a tad bit outdated, but his often cringeworthy humor makes The Office one of the more unique sitcoms out there, with Parks and Recreation following closely behind.

It would be an understatement to say that Michael leaving the office was a sad moment. But this episode was an absolute tear-jerker. Especially when Michael leaves Dunder Mifflin without saying goodbye. This episode was particularly sad since everyone — including Pam — was planning a goodbye party. The tears really begin to come when Michael, at the airport, is stopped and greeted by Pam carrying her heels in hand so that she can run up to him. Throughout the entirety of The Office, Michael forms and develops special relationships with specific characters, including those of Pam, Jim, and Dwight, so Pam and Michael’s farewell feels exceptionally sad.

1. “Customer Loyalty” Season 9, Episode 12

Pam and Jim Fight

Pam and Jim have always had a good relationship on The Office. There were a few moments here and there and in between where Pam and Jim had a hiccup in their relationship, but nothing was ever too serious for the comedic couple. However, later on in the series, after their marriage and Jim takes a new job far away, their relationship strains even further, with Pam and Jim not knowing how to appropriately handle the long-distance relationship. This leads to one of their major fights that shocks viewers with a harsh reality.

Anyone and everyone who is in a relationship or has had a relationship knows the heartache that comes from a strained relationship. In Pam and Jim’s case, Jim is trying his best to provide for his family while enjoying the work he does. But this means not being present for special moments like recitals. The strain reminds viewers of how fragile relationships can be at times, and how one mistake can lead to frustration from both parties. This was especially hard to watch, after having watched Pam and Jim’s relationship grow from working with one another to marrying each other, so to see Jim and Pam fight and Pam break down after the fact, out of fear of losing everything, will bring viewers to tears.