The Office: The Season Where Each Character Was The Funniest

Over its nine-season run, we were introduced to a number of brilliant characters, each with their own peaks and troughs in quality. Some of them made it through the show’s entire run, while a couple only appeared for a few episodes, but each brought their own unique comedic style to proceedings. The show itself might have gone drastically down in quality (as soon as Steve Carell left, many would say) but some of the characters remained beacons of happiness and humor for a long time.

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We’ve listed the main characters from the American adaptation of The Office and assigned them to the season that they made us laugh the most in.

10 Michael Scott (Season 3)

It’s almost impossible to whittle down the existence of Michael Scott into one stand-out season. The one thing that can be universally agreed upon is that the second he got on that plane is when The Office was doomed. As season three is often considered the show’s high-point, we’ve also categorized it as Michael’s thanks to his prominence. And the fact that this was the season in which we first met Prison Mike.

9 Dwight Schrute (Season 2)

Dwight Schrute was the secondary source of comedy from throughout The Office. In season one, he was effectively a clone of Gareth Keenan, but we’ve assigned him to season two here as it was where he really started to come into his own.

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This is the season in which Dwight started a massive, dramatic evacuation of the office, first showed his impressive abilities in martial arts and finally got promoted to Assistant Regional Manager.

8 Pam Beesley (Season 6)

While season six is actually the season in which Pam is the least present in The Office, it is also the one in which she develops the most. As she isn’t one of the main sources of laugh-out-loud comedy, she is one of the characters we follow for their story. As such, her recent marriage to Jim and the birth of their first child really allow us a window into her life.

7 Jim Halpert (Season 1)

While Jim certainly isn’t at his most important or interesting during season one, this is the season where it was his response that allows the audience to understand The Office. Michael is a little too like David Brent at this point and Dwight hasn’t come into his own, so we use Jim’s confused facial expressions to pinpoint normalcy as we’ve coming to know these characters.

6 Kevin Malone (Season 5)

Kevin is a consistent source of humor throughout The Office, even if he is tucked away at the back and often doesn’t get much time to shine. He takes home season five as this included not only his best moment but one of the most iconic moments in the show’s history: Kevin’s Famous Chilli.

5 Jan Levinson (Season 4)

Jan started out as Michael’s boss, before turning into his girlfriend, and finally, his emotional abuser. Season four was the pinnacle of their relationship and includes the legendary episode, ‘Dinner Party’. Often considered the show’s best episode, it paints Jan in the worst, yet most hilarious, light possible.

4 Creed Bratton (Season 9)

Giving Creed a definitive best season is almost as hard as Michael, simply because he has so many great moments despite his very rare appearances.

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The final moments of season nine in which he is revealed to have faked his own death to avoid paying for his past crimes before being found living in Ryan’s office is just comedy gold.

3 Robert California (Season 8)

Robert California is the easiest character to place into their own best season because, aside from a very brief cameo at the end of season seven, only appeared in season eight.

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This meant he was the only character to have been given ‘Main Cast’ billing despite only appearing in one season. While we missed Michael, his confusing and complex personality made him an endearing, creepy and hilarious stand-in boss.

2 David Wallace (Season 6)

Like Jan Levinson, David’s position across the entire nine seasons of The Office changed drastically. He started his life in the show as CFO of Dunder Mifflin, and eventually sold a toy vacuum to the US Military, purchased Dunder Mifflin and became CEO. In the middle of those big events, however, was season six. David had recently lost his job and temporarily deteriorated into an unemployed, unfocused and completely contrasting man who seemed to enjoy jam sessions with his son.

1 Toby Flenderson (Season 9)

One of the best recurring jokes in The Office was Michael’s pure hatred of Toby. Obviously, after Michael left, this fizzled out and left Toby to require some meaningful characterization. This came in the form of an obsession with the Scranton Strangler case. The reactions when he brings up the case are brilliant, but what is even more interesting is the way the show leads its audience towards a possible conclusion that Toby was actually the strangler himself.

NEXT: The Office: 10 Things About Jim That Would Never Fly Today



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