10 Saddest The Office Episodes, Ranked

Even though everyone agrees that The Office is one of the most hilarious sitcoms ever created, the series also contains nostalgic and harrowing episodes. The Office constantly combines absurd humor with bittersweet moments. This way, the audience sympathizes with all the characters and their relatable and moving story arcs.

Some of the saddest episodes of The Office include the main characters reflecting on their life, realizing not everything is how they expected it to be, or simply going through a rough patch. The Office makes the audience shed a few tears occasionally, elevating the series’ tone and showing the character’s true humanity.

10.“Take Your Daughter to Work Day” Shows Michael’s True Feelings

As the title suggests, in this episode, the Dunder Mifflin workers get to take their daughters to work. However, the sad part of the episode arrives when Michael shows the rest of the office a tape of a children’s show, Fundle Bundle, where he appeared as a kid. Michael says that when he grows up, he wants to be married and have 100 kids so he has 100 friends so no one can reject him.

The scene affects Michael, who realizes he didn’t achieve his dream. “Take Your Daughter to Work Day” shows great insight into Michael and explains why he constantly needs attention and validation. Seeing how lonely Michael truly feels is one of the saddest moments in The Office.

9.“Grief Counseling” Reflects on Death

In “Grief Counseling,” Michael learns that his former boss, Ed Truck, passed away in a terrible accident. This news deeply impacts Michael, especially because Ed was the former Regional Manager. In a way, this makes Michael think about his own mortality. He tries to cope with this death by creating a support group within the office, but no one takes it very seriously. At the end of the episode, Michael freaks out about a dead bird and decides to have a funeral for it.

While “Grief Counseling” discusses the issue of death with a lot of humor, it also portrays some of Michael’s insecurities and fear of passing away without being missed by anyone. Eventually, everyone in the office helps Michael process this death, and the episode ends on a sad yet hopeful note.

8.“Prince Family Paper” Makes Michael Realize the Consequences of his Actions

“Prince Family Paper” revolves around Michael and Dwight, who have to visit a local paper company, Prince Family Paper, to obtain information about their client list. The episode starts with a lot of The Office‘s usual comedy since Michael takes his job as a spy very seriously. However, it ends on a sad note when Michael realizes that the members of the company he’s going to destroy are actually good people.

In “Prince Family Paper,” Michael has a surprisingly insightful moment when he realizes that the greediness of the big companies is pointless, especially when it comes to ruining a good, hard-working family. Unfortunately, Dwight, ruthless as always, forces Michael to submit the list of clients they stole from the Prince Family Paper, and Michael has to go against his principles. This is one of the few moments when the audience empathizes with Michael, and it’s heartbreaking.

7.“Employee Transfer” Follows Michael and Holly’s Break-Up

Most people know that Michael has trouble making friends and connecting with women. When he finally finds a happy relationship, it’s heartbreaking to see it end. In “Employee Transfer,” David Wallace finds out about Michael and Holly’s romance and transfers her to Nashua, prompting the break-up.

Even though, in the beginning, Holly and Michael decide to continue the relationship through the distance, Holly changes her mind in the middle of the trip. This makes for a harrowing journey as Holly and Michael embrace for the last time and Michael goes back to Scranton with a broken heart.

6.“Boys and Girls” Crushes Pam’s Dreams

In “Boys and Girls,” when Janet leads a seminar for women in the workplace, Michael, feeling left out, initiates another seminar for men. The episode is filled with Michael’s stereotypically absurd and hilarious moments, but it has one scene that makes it one of the saddest episodes of The Office.

Throughout the seminar, Jan encouraged Pam to start taking graphic design classes since Pam loves to draw. However, when she tells Roy about it, he immediately reacts poorly, crushing Pam’s dream. While Pam tries to act okay, she starts crying in front of the camera. Pam’s journey in The Office is truly inspiring, but initially, it was hard to see her struggle with her career path and her romantic life simultaneously.

5.“Finale” Is A Nostalgic Goodbye

Series finales are always hard, especially when it comes to sitcoms. Even though The Office desperately needed closure, it’s always sad for the audience to see some of their favorite characters depart. An episode filled with nostalgia shows Dwight and Angela’s wedding, Jim and Pam leaving Scranton to follow Jim’s dream, and Pam’s mural of the office.

The Office‘s finale is about moving on to better things and finally getting a happy ending. It’s also about friendship and community. Even though Jim and Dwight hate each other for most of the show, Jim becomes Dwight’s best man at his wedding. It’s simply impossible to watch this episode without shedding a few tears.

4.“Goodbye, Michael” Says Farewell To One of the Best Characters in the Show

While The Office lasted nine seasons, the audience saw Steve Carell leave the show much earlier. Michael may have been obnoxious and insufferable at times, but he was undeniably the sitcom’s soul. Michael always had ridiculous ideas, but his heart was always in the right place.

In this episode, Michael decides to have a special moment to say goodbye to each employee. Jim even gets teary-eyed while telling him that he is a great boss. However, the most heartwarming moment is when Pam goes to the airport to say goodbye to Michael, as she wasn’t in the office that day. Pam and Michael hug in the middle of the airport in one of the most iconic scenes of The Office.

3.“Business School” Reinforces Michael and Pam’s Wholesome Friendship

In “Business School,” Pam is excited about her art show and invites everyone in the office to go. But when people don’t show up, Pam spends most of the episode alone standing beside her artwork. Worse, Oscar and his boyfriend show up only to criticize her projects. At the same time, no one in the gallery gets close to her drawings.

However, at the last minute, Michael arrives. He tells Pam that he’s very proud of her and even buys a drawing of the Dunder Mifflin building, which he later hangs out in the office. The scene is incredibly sweet yet harrowing, and it’s one of the moments when the audience falls in love with Michael and Pam’s friendship.

2.“Money” Consolidates Jim and Dwight’s Friendship

“Money” is one of the saddest episodes in The Office from beginning to end. It follows Dwight struggling with a failed relationship with Angela, Michael trying to keep another job to make his relationship with Janet work, and Darryl and Kelly going out but not being compatible.

However, the scene that the fandom always talks about is Jim making Dwight feel better after the latter starts crying for Angela. It’s heartbreaking to see Dwight, who usually pretends to be strong, break down like a little kid. Still, it’s also the moment the audience realizes Jim and Dwight care for each other.

1.“Customer Loyalty” Is The Most Heartbreaking Episode in The Office

Despite its low score on IMDb, “Customer Loyalty” has what everyone agrees is the most heartbreaking scene in The Office. After he decides to take a job in another city, Jim is having a hard time balancing his work life and his family. The tension in Jim and Pam’s relationship starts growing and reaches a peak when Pam fails to videotape their daughter’s ballet recital.

Jim quickly grows frustrated and shows his frustration to Pam on the phone. After she hangs up, she breaks down crying immediately, to the point where even one of the camera crew gets near her to make sure she’s okay. Even though Jim is a fan-favorite character, most people have difficulty processing this harrowing scene. Still, it gives the couple a more three-dimensional approach as the audience starts to see Jim and Pam dealing with life’s complications, which turns this moment into a bittersweet scene.