The Office: 10 Saddest Episodes | ScreenRant
Classic sitcom The Office featured heart-warming moments, silly running gags, and unforgettable jokes. However, the series also included heartbreaking episodes that left audiences in tears. The show captivated fans with the incredible love stories and difficulties that the Dunder Mifflin employees encountered, often dealing with heartbreak and loss.
They had as many sad days as happy ones. Of course, they often went through painfully emotional moments while a camera crew followed them around. The most painful episodes helped separate The Office from the rest of the shows, as it found a way to balance the silliest moments with the most heartbreaking.
10 Season 5 Episode 6: "Employee Transfer"
Michael Scott struggled to find love until he met his soulmate, Holly Flax. However, they sadly broke up after Dunder Mifflin assigned Holly to a new branch. The season 5 episode "Employee Transfer" featured Michael and Daryl moving Holly to her new home. The episode includes silly moments and classic jokes.
Regardless, the underlying sadness that Michael and Holly feel is easy to see. During the long drive, Holly realizes that a long-distance relationship won't work and breaks down. After a tough conversation, Michael and Holly agree to end the relationship.
9 Season 2 Episode 15: "Boys & Girls"
Initially, Pam Beesly was simply the receptionist married to warehouse worker Roy Anderson. Pam hated her job and seemed unhappy in her relationship. She always dreamt of being an artist but never followed through. In the season 2 episode "Boys & Girls," Jan offers to enroll Pam in a graphic design program.
Of course, Roy is entirely against the idea, and in the end, she decides against doing the program. During a talking head segment, Pam tries to justify not going but suddenly breaks down into tears. She was miserable with her job and relationship. At that moment, it seemed like she was stuck, and nothing would ever change.
8 Season 2 Episode 11: "Booze Cruise"
For years, Jim Halpert was madly in love with Pam. However, he kept his feelings to himself because she was engaged, even though Pam and her then-fiancé, Roy, were far from the perfect couple. In the episode "Booze Cruise," Michael takes the staff on a work cruise.
During the cruise, Captain Jack tells a story about proposing to his wife, which motivates Jim to disclose his feelings to Pam. The speech also inspires Roy. Before Jim can speak, Roy re-proposes to Pam and sets a date for the wedding. Pam and Roy celebrate with everyone except for Jim. Indeed, Jim can't hide the pain and anguish he feels. He's so upset that he even reveals his feelings for Pam to Michael.
7 Season 5 Episodes 14/15: "Stress Relief"
In the season 5 episode "Stress Relief," Dwight stages a fake fire to test the Dunder Mifflin employee's preparedness. Of course, the employees panic, and Stanley has a heart attack. However, Michael soon discovers he causes his staff a great deal of stress. Therefore, he arranges for them to roast him in the style of Comedy Central Roast.
The employees end up taking it too far and hurt Michael's feelings. His sad facial expression is a heartbreaking moment. Michael breaks down in tears and runs out of the warehouse in embarrassment. Eventually, the staff feels terrible and apologizes but not before Michael roasts them back.
6 Season 3 Episode 17: "Business School"
Michael and Pam formed a close friendship over the years. It all started in the season 3 episode "Business School", when they have a tough day. Michael speaks to Ryan's business class and finds out that his career is obsolete. At the same time, Pam has her first art show, and nobody attends.
Pam's hurt and disappointed as other artist's friends attend. Roy shows up but makes her feel worse, as do Oscar and Gil. In the end, Pam's heartbroken and embarrassed that nobody supported her. Michael shows up at the last minute and shares a touching moment with Pam.
5 Season 3 Episode 12: "Back From Vacation"
During season 3, Jim attempted to get over Pam and started dating Karen Filippelli. Of course, Pam was now the one madly in love with Jim. In the episode "Back From Vacation," Karen and Jim argue, which causes noticeable tension. Pam reluctantly offers advice to Jim that strengths the relationship with Karen.
Pam's conflicted between helping and wanting to be with Jim. She's heartbroken, upset, and alone. She might have missed her opportunity with Jim. Pam breaks down in tears and cries alone until Dwight shows up. He consoles Pam as she continues to cry. Of course, he says the wrong thing, but he's there for her nonetheless.
4 Season 4 Episodes 7/8: "Money"
Dwight Schrute's a crude but successful salesman. He seems cold-hearted but can be emotional too. He fell in love with Angela Martin from accounting, and they dated secretly for years. During season 4, Angela breaks up with Dwight after he euthanized her cat, Sprinkles. Dwight tries to hide his feelings, but he's devastated.
In the episode "Money," Jim and Pam stay at Schrute Farms. During the night, Dwight loudly sobs while thinking of Angela in a heartbreaking scene. Throughout the episode, Dwight can't hide the agony and heartbreak that he's feeling, and breaks down when Angela agrees to a date with Andy. In a memorable moment, Jim consoles Dwight in the stairwell and offers some helpful advice.
3 Season 2 Episode 22: "Casino Night" And Season 9 Episode 12 "Customer Loyalty"
Pam and Jim's relationship had many ups and downs. For instance, Jim professes his feelings for Pam in the season 2 episode "Casino Night." However, Pam rejects Jim even after kissing. Jim's so heartbroken that he moved away to a new branch. Of course, Pam and Jim eventually date and get married.
In the final season, Pam and Jim have relationship issues for several episodes. In the episode "Customer Loyalty," they get into a heated argument, and the conversation ends badly. Pam breaks down in tears and weeps until the boom operator consoles her. It's one of the saddest moments in part because Pam and Jim are such a beloved couple. Luckily, they solve their issues.
2 Season 9 Episodes 24/25: "Finale"
Critics gave the series finale rave reviews. It brought The Office to a satisfying conclusion but had fans in tears. The heartbreaking ending had characters moving on to new adventures in life and concluded numerous storylines. The characters not only said goodbye to each other but to fans as well.
The staff became closer over the years while starring in a documentary. At one point, Jim and Pam attempt to quit, but Dwight refuses. Instead, he fires them so he can give them a hefty severance package. It's a touching moment that brought smiles and tears to fans.
1 Season 7 Episode 22: "Goodbye, Michael"
Michael Scott could be an annoying and overbearing boss, but he loved his staff like family. In the episode "Goodbye, Michael," Michael doesn't tell anybody it's his last day. Jim is the only one to realize that Michael's leaving, and they have a heartfelt moment with Jim promising to see him tomorrow.
They shake hands while fighting back the tears. Pam's not at the office when Michael quietly leaves for the last time. In an incredibly touching moment, Pam chases Michael down at the airport. Michael leaving the show broke hearts and had fans sobbing. He said his final goodbyes and left to start a new life. The series wasn't the same after he left.
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