7 Most Surprisingly Emotional Moments in The Office

More than just a comedy, The Office included some surprisingly emotional moments throughout its nine-season run between 2005 and 2013. The American remake of The Office – developed by Greg Daniels – became one of the most successful and beloved sitcoms ever during its release, and has persisted as one of the greatest TV shows of all time. While celebrated as one of the funniest shows on TV, The Office also contained some incredibly heartfelt, emotional, and tender moments that became some of the series’ most memorable scenes.

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Led by comedy legend Steve Carell, The Office’s cast proved perfect at delivering both the sitcom’s comedic and emotional moments. John Krasinski, Rainn Wilson, Jenna Fischer, Angela Kinsey, and Carrel himself contributed to some of the series’ most poignant and heart-wrenching scenes, spanning the entire run of The Office. Now that a follow-up series, The Paper – starring Domhnall Gleeson and Sabrina Impacciatore – is gearing up to stream on Peacock in September 2025, we hope the impact of these emotional moments from The Office are repeated and remembered.

7) Michael and Darryl Sing in the Car (“Employee Transfer”)

During The Office season 5, episode 6, “Employee Transfer,” Michael (Carell) and Holly (Amy Ryan) relocate the latter to Nashua after she is transferred to her old branch. They’re driven by warehouse worker Darryl (Craig Robinson), but the pair realize that the distance will be too much to sustain their relationship, causing them to break-up on the journey. Michael and Darryl drive home without Holly, with the former being very upset, but Darryl tries to console him by singing the blues. This moment of connection and friendship between Michael and Darryl is one of the series’ most memorable moments.

6) Pam Cries to the Camera About Her Crushed Dreams (“Boys and Girls”)

The Office season 2 marked the start of the series’ deviation from the original British show’s storyline, and one new story was shown in episode 15, “Boys and Girls.” Jan (Melora Hardin) leads a “Women in the Workplace” seminar at Dunder Mifflin Scranton, where Pam (Fischer) expresses her desire to be a graphic designer. Jan suggests she should follow her dream, and Jim agrees, but Pam’s then-fiancé, Roy (David Denman), quashes the idea. This prompts a very emotional response from Pam, who cries during one of her talking heads, crushed under the weight of her unsupportive fiancé and dashed ambitions.

5) Jim Consoles Dwight in the Stairwell (“Money”)

The Office season 4 two-parter, “Money,” not only saw Michael declare bankruptcy after Jan’s firing from Dunder Mifflin, but also saw Jim and Pam stay at Dwight Schrute’s (Wilson) bed-and-breakfast, Schrute Farms. This was in the wake of Dwight and Angela’s (Kinsey) break-up, with the former still in intense grief. Usually depicted as enemies, “Money” saw Jim console Dwight after finding him sobbing in the Dunder Mifflin stairwell, expressing how painful his former crush on Pam was, and how powerful love can be. This was a beautiful shared moment between the two adversaries, teasing their evolution into firm friends.

4) Michael Questions David Wallace on the Phone (“Business Trip”)

Following Holly’s emotional transfer in The Office season 5, Dunder Mifflin CEO David Wallace (Andy Buckley) sends Michael on a restorative international business trip to Canada. However, despite making a sale, this trip only reminds Michael of how much he misses Holly, therefore prompting him to berate Wallace over the phone. We see Michael’s true emotional state at this moment, and it’s fantastic to finally see him standing up for himself. This scene also just reminds us of how heartbreaking Holly’s transfer was two episodes prior, making it even harder to watch.

3) Oscar Offers Angela a Place to Stay After Her Divorce (“Livin’ the Dream”)

The Office came to an end after its ninth season, and the last few episodes contributed to some of most heartbreaking episodes. Season 9, episode 21, “Livin’ the Dream,” saw Dwight finally promoted to Regional Manager after Andy (Ed Helms) quit, but Dwight’s rise coincided with Angela’s descent. She lost her husband, her home, and her cats, prompting Oscar (Oscar Nunez) to offer her a place to stay. Angela and Oscar often came to odds in The Office, so this was a beautiful moment of redemption and care from the latter, and a rare moment of vulnerability from the former.

2) Pam Watches Jim’s Video and Reads the Note (“A.A.R.M.”)

After “Livin’ the Dream,” the double-episode, “A.A.R.M.” sets up the series finale perfectly, most emotionally by resolving the marital problems in Jim and Pam’s relationship. After Jim refused to return to work at Athlead, Pam worries she isn’t enough for her husband, but this prompts Jim to enlist the documentary crew’s help to edit a video of their entire relationship, and Jim finally shows Pam the teapot note from Secret Santa in The Office season 2 – the contents of which are still private. This video makes both Pam and the viewer very emotional, looking back at The Office’s entire run.

1) Jim Says Goodbye to Michael (“Goodbye, Michael”)

Season 7’s “Goodbye, Michael” marked Steve Carrel’s departure from The Office, which is easily remembered as the entire series’ most emotional episode. Michael relocated to Buffalo to be with Holly, leaving Scranton a day before he said he would to forego emotional goodbyes. Jim works out this scheme, however, and promises to meet Michael for lunch “tomorrow” where he hopes to tell Michael “what a great boss [he] turned out to be.” With both Krasinski and Carrel tearing up, this moment is easily the most heartbreaking scenes in The Office’s history, but one scene might still have it beat.

Honorable Mention: Kevin Spills His Famous Chili (“Casual Friday”)

The Office became renowned for starting most of its episodes with hilarious, standalone cold opens, and the opening of season 5, episode 26, “Casual Friday,” is perhaps the most memorable. In the scene, Kevin Malone (Brian Baumgartner) arrives at the office early, bringing in his famous chili. As he narrates how proud he is of his family’s famous chili, he spills the entire pot on the carpet, and makes futile attempts to shovel it back into the pot. This is a truly heartbreaking moment of defeat from Kevin, who was routinely the butt of the joke in The Office.

What moments in The Office do you find the most emotional? Let us know in the comments!