Filling Out My The Office March Madness Bracket

Corona Quarantine 2020 allowed me to put way too much thought and time into this.

We may have no March Madness brackets, but today in honor of the 15th anniversary of the show, the twitter account for The Office released a bracket consisting of 32 of the series’ greatest episodes.

Full Bracket

In my previous blog I listed 64 films currently available to stream on Netflix to help you get through being stuck inside for weeks. (That can be found here.) But, in that blog I stated that most people usually just end up scrolling through Netflix for 40 minutes trying to decide what to watch before inevitably just choosing an episode of a TV show they’ve already seen before. For me, and so many others, this TV show is usually The Office, which is why I feel qualified to fill out this bracket.

Before I start selecting my winners, I have two quick thoughts on the bracket itself.

  1. I appreciate the fact that The Office twitter account knew not to include any season nine episodes besides “The Finale.”
  2. I could easily expand this bracket to 64, but instead of doing that I’ll just note some episodes I think should have been included: “Beach Games” (S3 E22), “Basketball” (S1 E5), “Weight Loss” (S5 E1-2), “Email Surveillance” (S2 E9), “Michael’s Birthday” (S2 E19), “The Fight” (S2 E6), “Cocktails” (S3 E17), “Gay Witch Hunt” (S3 E1), “The Coup” (S3 E3), “Goodbye, Toby” (S4 E14), “Customer Survey” (S5 E7), “The Duel” (S5 E12), “Delivery” (S6 E17-18), Happy Hour (S6 E21), “Sex Ed” (S7 E4), “Garden Party” (S8 E4).

Round One:

Top Left Region:

  • “Dinner Party” (S4 E9) vs. “The Client” (S2 E7)

Look, if I go too in depth on every single matchup then this blog is going to be way too long so I’ll try to keep it brief for the first couple rounds.

Even though when I wrote about The Office last month I ranked Season 2 as the best season, and “The Client” as the best episode from that season, the winner here just has to be “Dinner Party.”

Winner: “Dinner Party”

  • “Booze Cruise” (S2 E11) vs. “Casual Friday” (S5 E26)

As I continue to pick my winners, I imagine many of the Season 2 and Season 3 episodes are going to advance. This is one of those matchups where I have to say I love “Casual Friday” but unfortunately it just isn’t going to beat out a classic episode from one of the peak seasons.

Winner: “Booze Cruise”

  • “Money” (S4 E7) vs. “Goodbye Michael” (S7 E22)

It will be interesting to see how some of the great emotional episodes, like “Goodbye Michael,” fare against episodes beloved for their comedic value. At the end of the day, I love The Office because it makes me laugh. But, I’m also very much invested in the characters so even though it may not end up making a long run, “Goodbye Michael” is definitely worthy of a round one victory.

Winner: “Goodbye Michael”

  • “Niagra” (S6 E4-5) vs. “The Deposition” (S4 E12)

“The Deposition” is certainly a great episode, but unfortunately it got stuck with a very tough first round matchup. The two-part “Niagra” is one of the few late season episodes that could really make a deep run in this tournament.

Winner: “Niagra”

Bottom Left Region:

  • “Drug Testing” (S2 E20) vs. “Garage Sale” (S7 E19)

Even though this is a Season 2 episode vs. a Season 7 episode, this is actually a tough matchup to decide. “Drug Testing” is probably the better overall episode with more funny moments, but “Garage Sale” does have the most memorable moment in this matchup with Michael’s proposal to Holly coming at the end of the episode. At the end of the day, I have to go with my gut and what I think is the better start-to-finish episode though.

Winner: “Drug Testing”

  • “Benihana Christmas” (S3 E10-11) vs. “Christmas Party” (S2 E10)

The only two Christmas episodes to make the bracket square off against each other in round one, and it’s not an easy decision. In a weird way I think the fact that “Christmas Party” is a single episode and “Benihana Christmas” is two parts, actually helps out “Christmas Party.” There are so many great moments condensed into those 21 minutes, so there really isn’t a wasted second in the whole episode.

Winner: “Christmas Party”

  • “Murder” (S6 E10) vs. “Sexual Harassment” (S2 E2)

This one was a fairly easy decision to make. “Sexual Harassment” is an incredible episode, and while I enjoy “Murder,” I have always found it to be just a little bit overrated if I’m being honest.

Winner: “Sexual Harassment”

  • “The Injury” (S2 E12) vs. “Fun Run” (S4 E1)

Probably the toughest matchup in this whole region, both of these episodes are amazing. Season 2 has been cleaning up in this region winning all three of the previous matchups, but unfortunately I don’t think it’s winning a fourth. “Fun Run” is one of the best 40-minute episodes of the whole series and kicked off Season 4 in an incredible way.

Winner: “Fun Run”

Top Right Region:

  • “The Alliance” (S1 E4) vs. “Product Recall” (S3 E21)

The six episode first season finally makes its debut in this tournament with “The Alliance” but it’s going up against a real tough opponent in “Product Recall.” I am a big defender of Season One but that doesn’t mean I can give the nod to “The Alliance” in this matchup. “Product Recall” is just too good.

Winner: “Product Recall”

  • “Casino Night” (S2 E22) vs. “The Surplus” (S5 E10)

For as funny and memorable as “The Surplus” is, “Casino Night” is, in my opinion, a far superior episode. “Casino Night” is one of those few special episodes of The Office that is iconic for its comedic moments, as well as its emotional moments.

Winner: “Casino Night”

  • “The Dundies” (S2 E1) vs. “Business School” (S3 E17)

This is another matchup with a very good episode going up against an iconic episode that just cannot lose in the first round. “The Dundies” is too good and too important to the show as a whole to lose here.

Winner: “The Dundies”

  • “Threat Level Midnight” (S7 E17) vs. “The Job” (S3 E24-25)

This is, without a doubt, the toughest matchup in this region. The two-part finale to Season Three, “The Job,” is a wonderful episode and contains moments that are very pivotal for some of the series’ most important plot lines. However, “Threat Level Midnight” is one of the most memorable episodes in the history of The Office, and that has to count for something.

Winner: “Threat Level Midnight”

Bottom Right Region:

  • “Safety Training” (S3 E20) vs. “Broke” (S5 E25)

This was a fairly easy decision. I’m honestly surprised that “Broke” is the episode containing The Michael Scott Paper Company that they decided to include. It’s a fine episode and it brings Michael, Ryan, and Pam back to Dunder Mifflin, but as a whole I don’t find it as great as some of the other Michael Scott Paper Company episodes.

Winner: “Safety Training”

  • “The Finale” (S9 E24) vs. “Branch Wars” (S4 E6)

“The Finale” advancing is going to make things tricky because it is just such a hard episode to compare to others, considering the circumstances. Still though, I can’t deny that it was a great final episode and deserves to move on past the first round.

Winner: “The Finale”

  • “Scott’s Tots” (S6 E12) vs. “Diversity Day” (S1 E2)

The most uncomfortable half hour in the history of sitcom television, “Scott’s Tots,” just simply cannot enter the second round of this tournament. I thought about choosing it for a second because it still is an iconic episode in its own way, but I just couldn’t do it.

Winner: “Diversity Day”

  • “Pool Party” (S8 E12) vs. “Stress Relief” (S5 E14-15)

This is another far too easy decision. While “Pool Party” is a solid late season episode and probably one of the best Robert California episodes, it is not in the same league as “Stress Relief.”

Winner: “Stress Relief”

Round One Results:

Round One Results

Sweet Sixteen:

Top Left Region:

  • “Dinner Party” (S4 E9) vs. “Booze Cruise” (S2 E11)

I hate to make this so brief because “Booze Cruise” genuinely is one of the better episodes of all of Season Two, but “Dinner Party” is just one of those episodes that will cruise through these first couple rounds.

Winner: “Dinner Party”

  • “Goodbye Michael” (S7 E22) vs. “Niagra” (S6 E4-5)

The worst case scenario for “Goodbye Michael,” an episode strengthened by its emotional moments, is for it to run into an iconic episode that has equally great emotional moments as well as great comedic moments, like “Niagra.” For that reason, “Niagra” simply has to advance here.

Winner: “Niagra”

Bottom Left Region:

  • “Drug Testing” (S2 E20) vs. “Christmas Party” (S2 E10)

Two great Season Two episodes are going up against each other here in a very tough matchup. This may be a little unfair, but I think the fact that “Christmas Party” is a Christmas episode gives it an immediate advantage here. The Office’s Christmas episodes are special, and “Christmas Party” is probably the best one.

Winner: “Christmas Party”

  • “Sexual Harassment” (S2 E2) vs. “Fun Run” (S4 E1)

Even more so than the last matchup, this is a real toss-up. Both “Sexual Harassment” and “Fun Run” contain iconic moments in the history of the series. Because this is virtually a tie, and I don’t want Season Two to just dominate this entire bracket, I’m going to go with “Fun Run” here.

Winner: “Fun Run”

Top Right Region:

  • “Product Recall” (S3 E21) vs. “Casino Night” (S2 E22)

“Product Recall” is amazing, but “Casino Night” is a legitimate final four contender that simply has to advance here. As we go deeper into this bracket, it is going to be the truly iconic episodes that emerge, and unfortunately for “Product Recall” it doesn’t come close to “Casino Night” in terms of iconic status.

Winner: “Casino Night”

  • “The Dundies” (S2 E1) vs. “Threat Level Midnight” (S7 E17)

Honesty time, I love “Threat Level Midnight” but I think it is more beloved for the idea than the actual episode itself. The episode is good, but maybe just a tad bit overrated at this point. Truthfully, I might prefer the table read of Michael’s script that takes place in “The Client” to the full Season Seven episode itself. Also, c’mon it’s “The Dundies.”

Winner: “The Dundies”

Bottom Right Region:

  • “Safety Training” (S3 E20) vs. “The Finale” (S9 E24)

In the last round, I stated that “The Finale” was going to be difficult to compare to other episodes. I think that is hurting its chances in this matchup because truthfully, even though I love “The Finale,” if you were to ask me which of these episodes I’d be more inclined to put on on a random day, it would be “Safety Training.”

Winner: “Safety Training”

  • “Diversity Day” (S1 E2) vs. “Stress Relief” (S5 E14-15)

An unfortunate matchup for “Diversity Day,” which is probably one of the most important episodes in the history of The Office. However, there’s just simply no way “Stress Relief” is exiting in the second round.

Winner: “Stress Relief”

Sweet Sixteen Results:

Round Two Results

Elite Eight:

Top Left Region:

  • “Dinner Party” (S4 E9) vs. “Niagra” (S6 E4-5)

This is the first real test for “Dinner Party.” “Niagra” is a formidable opponent worthy of this matchup. “Niagra” is an incredible two-part episode. It is full of hilarious moments, while also containing real emotional moments involving Pam, Jim, and their wedding. It’s probably one of the best wedding episodes in the history of television. Also, I believe it is the true end of The Office‘s prime and the show never really was the same after “Niagra.” With all that being said though, “Dinner Party” was essentially a lock for the final four once this bracket began. It’s sad to say because I really do love “Niagra” but unfortunately for that episode, “Dinner Party” is just going to have to advance here.

Winner: “Dinner Party”

Bottom Left Region:

  • “Christmas Party” (S2 E10) vs. “Fun Run” (S4 E1)

This is a very tough Elite Eight matchup to choose. Both “Christmas Party” and “Fun Run” are not only incredible episodes from a quality standpoint, but also two unique episodes because one is a Christmas episode and the other is the opening episode to a season. The fact that “Christmas Party” is a Season Two episode does give it some advantage here. Also, while “Christmas Party” is probably the best Christmas episode of The Office, I can think of several other debut episodes of a season that I hold in similar or higher regard than “Fun Run.” That isn’t a knock against “Fun Run” though, because it is genuinely one of the best Season Four episodes and clearly one of the better episodes of the whole series since it has made it this far, but when it comes down to the Elite Eight difficult choices have to be made and the slightest edge can give the win to one episode over another.

Winner: “Christmas Party”

Top Right Region:

  • “Casino Night” (S2 E22) vs. “The Dundies” (S2 E1)

Literally the first and last episodes of Season Two are facing off here with a chance to go to the final four on the line. The best season of The Office, Season Two, is full of so many great episodes and was clearly bookended by two of the best of the whole series. Both “Casino Night” and “The Dundies” deserve their spots in the Elite Eight. This is a very difficult decision because The Dundies as a thing within The Office universe is probably more iconic than any one single thing that appears in “Casino Night.” But, “Casino Night” as a whole is probably a more iconic episode when it comes to story and its impact on the overall plot of the show. At the end of the day, because “The Dundies” really set off The Office into its prime in a major way, I think I have to go with it as my winner in this incredibly close matchup.

Winner: “The Dundies”

Bottom Right Region:

  • “Safety Training” (S3 E20) vs. “Stress Relief” (S5 E14-15)

In a shocking turn of events, “Safety Training” was the only Season Three episode to make it to the Elite Eight. This matchup is similar to the “Dinner Party” vs. “Niagra” matchup because it is really the first difficult test “Stress Relief” has faced after cruising through the first two rounds. I love “Safety Training,” all the warehouse guys are absolutely incredible, and Steve Carell does some of his best work of the whole season in that episode as well. With that being said, “Stress Relief” is another episode that just has to make the final four. Between its two parts, it has three of the most iconic and hilarious scenes in the history of the show. My apologies to “Safety Training” and Season Three as a whole, but this matchup has to go to “Stress Relief.”

Winner: “Stress Relief”

Elite Eight Results:

Round Three Results

Final Four:

  • “Dinner Party” (S4 E9) vs. “Christmas Party” (S2 E10)

Well, we’ve finally reached the final four and unfortunately we’re starting it off with a somewhat anti-climactic matchup. I say that because honestly I think “Niagra” was a tougher test for “Dinner Party” than “Christmas Party” is. Don’t get me wrong, “Christmas Party” is great, however, I think “Niagra” is overall a better episode than it, and I obviously think that “Dinner Party” is a better episode than both of them. I salute the run of “Christmas Party,” it had a great tournament and really showed up for all the Christmas episodes of The Office. However, as many probably could have guessed from the start, “Dinner Party” is advancing to the finals.

Winner: “Dinner Party”

  • “The Dundies” (S2 E1) vs. “Stress Relief” (S5 E14-15)

This is a matchup of two truly iconic episodes. Both “Stress Relief” and “The Dundies” are incredibly important to The Office as a whole. “Stress Relief” may be the more mainstream pick because it has more “meme-able” moments but I still think it is the correct choice. The greatness of “The Dundies” can’t be understated though. It is truly one of the most important episodes in the history of the show and marks the shift from what the first season was to what the show would ultimately go on to be. I believe “The Dundies” is where the version of Michael Scott that we would come to know and love was truly born. With that being said, “Stress Relief” just has too many moments of undeniably great comedy to stop it from making the finals. I don’t want to say this was an easy decision though because it really was not.

Winner: “Stress Relief”

Final Four Results:

Round Four Results

The Championship:

  • “Dinner Party” (S4 E9) vs. “Stress Relief” (S5 E14-15)

Let me start this off by saying how shocking it is that the finals came down to an episode from Season Four and another from Season Five. That just goes to show the strength of these two episodes though. Even though they may not be from Season Two or Season Three, they have established their place as two of the greatest episodes in the history of The Office. The hardest part about this decision is the fact that “Dinner Party” is a normal-length episode and “Stress Relief” is a two-part episode. The reason that makes the decision so difficult is because “Dinner Party” is probably funnier from start to finish and has less “filler” scenes than “Stress Relief,” but “Stress Relief” has some of the best scenes in the history of the show spread out over its 40 minute runtime. “Dinner Party” is one of the funniest 22 minutes in the history of television, I simply can’t deny that. But, “Stress Relief” has three scenes — the opening scene, the CPR scene, and the boom roasted scene — that I think has to solidify it as the champion here. Even though it may have the somewhat forgotten B-story that focuses on Pam’s parents going through a divorce, and “Dinner Party” may be more solid from start to finish. Those three scenes I mentioned, along with Michael’s roast, are so good that the edge still goes to “Stress Relief” here. Forgive me for being basic.

Champion: “Stress Relief”

Final Bracket:

Final Bracket


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