Dunder Miffed: The 10 Most Entertaining Rivalries On The Office

The bulk of The Office rides on the entertaining and over-the-top feuds between the ridiculous characters, whether it’s work- or love-related.

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.

10 Jim Versus Dwight

The Office Jim Dwight John Krasinski Rainn Wilson

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

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

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

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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

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

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

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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

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

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

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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