Ten years ago on Sept.27, 2007, NBC’s The Office began its journey through a shortened fourth season due to the ongoing Hollywood writer’s strike. Ten years later, Season 4 of The Office stands the test of time as the most important during the show’s nine-season run.

Yes, that’s right — Season 4 of The Office is the most important in the show’s history, story-wise. Here are several standout moments that set this season apart from the other eight during the series’ entire run.

Episodes 18 & 19: “Goodbye, Toby” – Say Hello to Holly Flax

Let’s start off with one of the biggest character introductions ever on The Office, which occurred during the Season 4 finale, “Goodbye, Toby.”

After Toby announced earlier in the season that he would be leaving for Costa Rica, the door opened up for a new HR rep to take his place in the annex. During the season finale, not only did we meet Toby’s replacement in Holly (Amy Ryan), but also Michael Scott’s future wife.


Holly’s introduction to the show was fantastic. First, she’s hated by Michael and Dwight simply because she’s the new HR rep, then she becomes sympathetic toward Kevin because Dwight tells her the accountant is “special. Later on, she becomes the victim of a raccoon in her car, once again due to Dwight.

After the raccoon is freed, Michael uses one of his weirdest complimentary lines on Ms. Flax:

“Holly is the best thing that has happened to this country since World War 2.”

Just the simple fact that we meet Michael’s future wife is enough to make Season 4 a top three season.

Episodes 18 & 19: “Goodbye, Toby” – Ryan was arrested

Holly wasn’t the only character to grab headlines in this episode. Five characters actually went through life-changing events in the season’s finale. One of them was good ol’ Ryan Howard.

Ryan wasn’t in the finale for very long, but that’s because he was only shown in a video getting arrested for fraud related to his baby “Dunder Mifflin Infinity.”

This arrest led to Ryan’s eventual redemption arc and also opened the door for Charles Miner (Idris Elba) to take Ryan’s job, leading to the Michael Scott Paper Company and other Season 5 shenanigans.

All in all, Ryan’s arrest had the biggest impact on corporate during the show’s run.

Episodes 18 & 19: “Goodbye, Toby” – Jan is pregnant!

Michael’s former flame and boss Jan Levinson had an interesting arc during Season 4. She went crazy in one of the season’s best episodes (“Dinner Party”) and then later decided to become a mother.

Jan deciding to become a mother had a big impact on Michael’s life and kind of delayed his relationship with Holly at one point. On top of that, Jan’s decision to get pregnant kept her on the show in general.

While this was a major twist in the finale, it wasn’t as big as Holly’s introduction or Ryan’s arrest and definitely wasn’t as impactful as what happened to Dwight and Angela.

Episodes 18 & 19: “Goodbye, Toby” – Dwight and Angela were caught by Phyllis

The final scene of Season 4 is one of the best season-ending moments on The Office. Due to Phyllis catching Dwight and Angela sleeping with each other IN THEIR ACTUAL OFFICE shortly after Angela agreed to marry Andy, the following occurred in later seasons:

  1. Phyllis takes over as the head of the Party Planning Committee
  2. Dwight and Andy have a duel over Angela
  3. Andy and Angela break up

Those three events were big enough to create a ripple effect throughout the rest of the series as Dwight and Andy bonded over being cheated on, the PCC was never the same, and Andy and Angela never actually got married.

The finale of Season 4 played a big role in making season four the most important of the nine the show had, but there were other big episodes during that season as well.

Episodes 1 & 2: “Fun Run” – Michael hits Meredith and Jim and Pam become official

The first scene of the season is quite the memorable one as we see Michael get ready for work and then promptly hit Meredith with his car. This leads us on one heck of a journey as Michael proceeds to learn Meredith has rabies and then hosts a fun run.

But that wasn’t the biggest moment in the season’s premiere as we also learned Jim and Pam were officially dating. While the viewers (and camera crew in the show) learned this in the season’s premiere, the rest of the show’s characters didn’t learn this until episode 3. Still, the fact that Jim and Pam became official was the biggest beginning of a relationship on the show.

Episode 10: “Branch Wars” – Karen is the regional manager in Utica

Season 3 ended with Jim dumping Karen and then promptly asking Pam out. What wasn’t shown, however, is what ended up happening with Karen. But in the Season 4 premiere, we learned that Karen had left her job in Scranton shortly after she and Jim ended things.

Surprisingly enough, we didn’t find out what was next for Karen until episode 10 until it’s revealed that she’s the regional manager in Utica. Moving Karen off the show was important to the series as a whole, but it worked out well for Rashida Jones, who went on to play Ann Perkins for six seasons on Parks and Recreation.

Episode 13: “Dinner Party” – The most awkward dinner party evre

When I first watched The Office, this episode was so painful I thought I could never watch it again. But the thing is, it may be the best episode of the season because as painful as it is, it’s also so great. From Jan’s candles being deadly, Jim and Pam’s failed escape, the osso buco not going in the oven early, a terrible game of charades, a Dundie Award finding Michael’s plasma TV, and finally the arrival of Dwight and his girlfriend/nanny, this episode was hilarious.

Oh, and did we mention this was really the final straw for Michael and Jan’s relationship? That was pretty important for the show going forward.


The Michael, Jim, Pam, Dwight arcs

The final thing that makes Season 4 the most important during The Office’s series run is that at least two MAJOR events happened to each of the show’s four main characters.

Michael: He finally broke up with Jan (kind of sort of) and met Holly.

Jim: He became official with Pam and begins to test the waters of being manager when Michael is out.

Pam: She became official with Jim and gets accepted into her art program in NYC.

Dwight: The Angela fiasco and we see large portions of Dwight’s farm.

While there were other seasons where the four main characters experienced big events, what our fearless foursome went through in Season 4 made the biggest impact on their lives in Scranton.

Seasons 2 and 3 were funnier and Season 9 was definitely more emotional, simply because it was the show’s final season, but Season 4 was the most important for The Office‘s series run.

More life-changing events happened during this season than in any other to our favorite characters and even the supporting ones such as Ryan (getting arrested), Jan (becoming pregnant), Holly (being introduced), Toby (going away), Stanley (DID I STUTTER), etc. had memorable moments.

Four years since The Office ended provides enough distance to look at the entire series, making it clearer that Season 4 was the most important for the show. That season began 10 years ago and boy, was it a good one.

About David Lauterbach

David is a writer for The Comeback. He enjoyed two Men's Basketball Final Four trips for Syracuse before graduating in 2016. If The Office or Game of Thrones is on TV, David will be watching.