Dunder Miffed: The 10 Most Entertaining Rivalries On The Office

There are very few television comedies that have been able to compete with The Office. The show revolves around the employees of the seemingly dull paper company, Dunder Mifflin. However, the combination of outrageous antics with these somewhat cringy characters somehow make for one hilarious spectacle.

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The bulk of the show rides on the rivalries that are commonplace within the office. Whether it’s work- or love-related, the one-on-one competitions are persistent. Every character has been involved in at least one feud at some point or another. It’s hard to narrow down which rivalry has been the most entertaining, but here are ten of some of the very best duels from The Office.

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The Office Jim Dwight John Krasinski Rainn Wilson
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10 Jim Versus Dwight

The Office Jim Dwight John Krasinski Rainn Wilson

This show may have never picked up steam like it did if not for the rivalry between Jim and Dwight. The show opens with Jim, the mild-mannered salesmen, pulling pranks on his colleague Dwight. Dwight, who unlike Jim, holds his position as a paper salesman to high regard, does not find Jim’s antics funny at all.

Their opposing personalities cause controversy between the two throughout the entire series, with Dwight simply acting as the front for Jim’s office pranks. Despite this, Jim and Dwight end up forming a close friendship by the season's finale.

9 Dwight Versus Andy

Ed Helms, Steve Carell, and Rainn Wilson as Andy, Michael, and Dwight in The Office

The feud between Dwight and Andy stems from their mutual interest with the accountant, Angela. Dwight and Angela have a coveted relationship from the end of the second season until sometime in the fourth. The relationship ends after Dwight kills Angela’s cat. Angela then starts dating Andy Bernard, the new salesmen at Dunder Mifflin.

While there couldn’t be a worse combination, Andy ends up proposing to Angela—much to the dismay of Dwight, who is still in love with her. Angela and Dwight resume a sexual relationship throughout Angela’s engagement. It’s not until much later that Andy finds out about this, thanks to Michael. Andy then demands that Dwight fight him outside, where he tries to run him over with his car.

8 Angela Versus Oscar

After Dwight and Andy realize that Angela has been sleeping with both men, the two reconcile and decide that neither wants anything to do with her. Angela remains single until she meets Robert Lipton (a.k.a the Senator) in season 8. Angela eventually marries the Senator and has a baby with him (later revealed to be Dwight's child).

In season 9, however, Angela finds out that her husband is gay and has been having an affair with her coworker, Oscar. Angela tries to elicit the help of Dwight to have Oscar killed, without mentioning that Oscar is the target. Once he realizes this, Dwight stops the assassination. Angela then yells at Oscar for turning her husband gay. Oscar rebuts and eventually the two settle their differences. The Senator decides to announce publicly about his homosexual relationship, but it is revealed that he actually has a third lover—that Angela and Oscar both didn’t know about.

7 Phyllis Versus Angela

As head of the Party Planning Committee, Angela seems to take pleasure in bossing Phyllis around. Angela is hot-headed and demanding, which is initially intimidating to Phyllis, who is meeker. However, Phyllis gradually starts to gain confidence and works up the courage to stand up to Angela. Angela rebuttals by talking down to Phyllis and continues to treat her poorly.

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The tables eventually turn after Phyllis realizes that Dwight and Angela are having an affair. By the next season, Phyllis is head of the Party Planning Committee and gleefully proceeds to treat Angela in the same condescending manner that she gave Phyllis over the years.

6 Michael Versus Toby

For some inexplicable reason, Michael Scott, manager of Dunder Mifflin’s Scranton Branch, loathes his HR representative. Toby Flenderson is a shy and non-threatening character whom Michael Scott hates with a fierce passion. Michael continuously undermines Toby, while blatantly stating his hatred for him.

Toby never sticks up for himself, even when Michael tries to get him fired by planting “drugs” in his desk. Toby appears to not take Michael’s hatred to heart, but in the episode “Double Date,” Toby expertly teaches Pam the best way to punch Michael (who broke up with Pam’s mom on her birthday).

5 Jim Versus Roy

Jim Pam and Roy From The Office

Before Jim and Pam's inevitable relationship, Pam was engaged to the warehouse worker, Roy. While it was always evident that Jim and Pam had feelings for each other, Pam refused to act on them because of her long-term engagement to Roy. Jim was also respectful of this relationship until he could no longer hide his feelings.

With mere months before Pam and Roy’s wedding, Jim finally confesses his love for Pam and kisses her. Pam doesn’t relent to her feelings and nothing comes of the relationship for a while. However, Pam does call off her wedding and eventually tells Roy about Jim kissing her. Despite their relationship being over, Roy storms into the office and tries to fight Jim. The fight is intercepted by Dwight, who sprays pepper spray in Roy’s eyes.

4 Dwight Versus Michael

Michael and Dwight the Office

Dwight is subconsciously fighting for Micahel’s job as regional manager. Although Michael offers Dwight the fake position of “Assistant to the Regional Manager,” Dwight eventually wants more. In the third season episode, “The Coup,” Dwight meets with Jan Levinson to express his interest in taking Michael’s job.

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Dwight has always been extremely loyal to Michael, so when Jan calls to tell Michael of Dwight’s deception, he is offended. Michael leads a ruse to make Dwight believe that he is the new manager. Eventually, it falls through and Michael confronts Dwight. After begging for forgiveness and offering to do Micahel’s laundry for a year, Dwight returns to being his loyal right-hand man.

3 Pam Versus Karen

This unintentional rivalry happens after Michael brings his staff on a beach day outing. Pam has broken off her relationship with Roy, but in the meantime, Jim started dating Karen Filippelli, who he met while working at the Utica Dunder Mifflin location.

Jim and Pam resume their usual, albeit awkward, friendship, although they continue to flirt in front of Karen. At the end of their beach day, Pam summons up the courage to tell Jim that she called off her wedding for him and misses them being best friends. This puts a bit of a sour taste in Karen’s mouth, especially as she and Jim continue dating.

2 Ryan Versus Mindy

Ryan Howard is the office temp who holds an unhealthy and somewhat abusive relationship with the customer service representative, Kelly Kapoor. Ryan is perceived as an arrogant and egotistical young man, while Kelly is vapid, vane, and only cares about her appearance and celebrity culture.

The two have a tumultuous relationship for the bulk of the show, even with them constantly fighting with each other. Each time they break up, they try to impose jealously. Kelly goes as far as to flaunt her relationship with Darryl from the warehouse. Kelly even gets married and has a baby with another man, but she and Ryan end up running off together, with Kelly leaving the baby with her husband.

1 Michael Versus Charles

After Michael unexpectedly gives his two weeks notice to Dunder Mifflin, he begins to goof off at the office. In charge is the new corporate vice president, Charles Miner. Michael’s playful and relaxed attitude does not mesh well with Charles’ strict no-nonsense persona. It was Charles’ micro-managing that led Michael to give his two weeks in the first place.

When Michael announces he is starting the Michael Scott Paper Company, Charles fires him immediately. He has Michael escorted out of the office, but Michael returns to try to persuade the staff to join him. As he’s crawling on the floor to remain undetected, Charles sees him and threatens to physically escort Michael out himself. Michael relents and leaves the office.

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