Greetings, reader!
With Halloween just around the corner, I shall dedicate my last post of October 2023 to spooky season - not in the usual manner of discussing horror films, but by taking a look at television's finest Halloween tradition: the Halloween Heists from Brooklyn Nine-Nine (2013-2021). Every season of the show's run had its own take on the heist, and this is my ranking of these instalments.
8. Valloweaster (Season 7 Episode 11)
"The vests add nothing"
"The vests add gravitas"
"Your butt adds gravitas!"
It was a smart move to switch things up in later seasons, so that the heist tradition could keep on going without getting stale. But still, there's no getting around the fact that the later ones that don't take place on Halloween just aren't quite as dynamite as the original Halloween heists (there is one exception, which we'll get to later).
There are glimpses of brilliance in this taking-place-across-multiple-holidays instalment, including the hilarity of the characters being skeptical of an actual disaster being a mere heist scheme and the fact that technically, in one way of interpreting the ever-contested score, Rosa (Stephanie Beatriz) has won three times and a filing cabinet has won once due to this episode. But, a lot of the actual schemes and reveals during the heist do feel a bit tired, feeling like the tradition was past its prime albeit still entertaining.
7. Cinco de Mayo (Season 6 Episode 16)
"You tricked me, Rosa! And then you shipped me to New Jersey!"
"First of all, grow up. Second of all, how'd you get back here so fast?"
The season 6 heist is the first one to break from the tradition of taking place on Halloween. Like I said - a smart move, but still, that alone can't save the tradition to being just a bit beyond its best days. The Cinco de Mayo heist is like Fast & Furious 6 (2013) - the fourth F&F had been bigger and better than previous sequels and the fifth had perfected the recipe by being even bigger and better - and then the sixth one proved that if you go more large-scale from there, it starts to feel bloated.
Now, I'm not saying that Cinco de Mayo is bad - there's a lot to enjoy, including the Scully's (Joel McKinnon Miller) twin brother reveal, and as is the case with every heist episode, it is one of the better ones in its season. But when compared to the high standard of other heist episodes, there's a lot in Cinco de Mayo that feels like trying just a bit too hard, or simply existing after the first five Halloween Heists had perfected the recipe and there was nothing left to outdo. It's still entertaining as hell.
6. Halloween IV (Season 4 Episode 5)
"Gina! Of course! It all makes sense - except for the parts I don't understand and the fact that I still kind of think Terry did this"
By season four, the tradition was an anticipated fan favorite, the writers were tasked with keeping the concept fresh with new twists, and they still had quite a few punches left in them at this point. The main reason for IV being ranked lower than the other actual Halloween-set heists is mainly that this one has the least epic final reveal - I don't care about Gina (Chelsea Peretti) as much about the other main characters so her victory doesn't feel so special, and how the victory came about is semi-clever but not as mind-blowing as the final reveals in the other heists.
Still, the opening act of the episode is delicious and classic stuff, and there are plenty of memorable moments. The tradition of everyone getting more competitive and downright mean (in a hilarious manner) each year really starts to find its voice around year four, and the trash talking is a joy to follow.
5. Halloween (Season 1 Episode 6)
"Can you magically make everyone kind, sober and fully dressed?"
"Kind, sober and fully dressed. Good news everyone, we found the name of Santiago's sex tape"
There's something special about the original. It may be the least flashy, least high-stakes and least blockbuster our of the heists, but the tradition works so well because it started off small enough that there was room to grow on and the growth arch was a wonder to follow. Here we have but a delightful battle of minds between Jake (Andy Samberg) and Holt (Andre Braugher), and the episode is simply really good - so good, that they decided to make another one the next year, and so forth.
Also, the final reveal in this one is very clever and feels like a true payoff. Some real Ocean's Eleven (2001) vibes right there.
4. Halloween II (Season 2 Episode 4)
"We're doing it Boyle! We're Tokyo Drifting!"
The second Halloween Heist is much like the first, but with a classic one-notch-up improvement: it's just a tad bigger and better, a tad better-thought-out, and an overall solidification of what would become a beloved tradition. It's still very much Jake vs. Holt this time, as Heists #3 and #4 would be where the other characters started to actively participate more. But one more round of Jake vs. Holt was just what we needed, and boy, the show sure delivered.
Halloween II is pure and simple fun - it's not as grandiose as the future ones nor does it need to be. The heist tradition was built one block at a time, and this building block was an important one. Also, the final twist is one for the ages.
3. Halloween III (Season 3 Episode 5)
"You drank a soda? Not sure that's the worst thing in the world"
"It was the worst thing in the world. Worse than a fruit-forward Riesling. No, I'm not exaggerating"
Halloween III hits a true sweet spot: the tradition has grown more beloved, more grand-scale and more high-stakes than the previous ones, yet not even the most cynical fans could call the tradition overdone or stale, as everything is still so fresh and the writers have a blast with the opportunities presented by the premise.
Also, hats off to Amy (Melissa Fumero). Her win is well-deserved, cementing her as a true mastermind and amazing detective/genius.
2. The Last Day (Season 8 Episodes 9-10)
"Wunch's grave"
"Wow, did Terry put up a balloon arch just for the heist?"
"No, that was me. I come every week to install a fresh one"
Oh man, this one hits hard. By the final season, the once-per-season heist tradition was such an integral part of the show's DNA that they decided to utilize it for the series finale. And this was the right choice, as can be surmised from The Last Day's #3 ranking in my blog post of the greatest sitcom series finales of all time. It's the perfect setting for B99's final episode.
Even though the concept had become a pit past its prime in seasons 6 and 7, this spectacle doesn't suffer from that - there were no punches left to pull at this point, allowing the writers to truly give their everything with just the craziest twists and turns. Amy tricking Jake into thinking he was in a coma for years (and that Amy moved on and remarried) is such a perfect peak for eight years of heist plots growing more elaborate and delightfully mean-spirited.
Also, pretty much every character has the idea of manipulating the final heist into a means of saying their sweet goodbye to the others. These overlapping plans make everything a bit messy, but in a sweet and tongue-and-cheek fashion. A nice bow on things, this one.
1. HalloVeen (Season 5 Episode 4)
"And, it's midnight! So I guess I'm an amazing human/genius!"
"Yeeah...although...you might want to read the inscription on the belt"
Nothing can quite beat this one. From the hysterical cold open, through everyone separately coming up with the plan to hide microchips in Terry's (Terry Crews) yoghurt, all the way to the final reveal - Jake's proposal to Amy, which I dare to call the single greatest moment in the whole damn series. Not only is HalloVeen the best instance of the Halloween Heist tradition, it's the best episode in all of Brooklyn Nine-Nine. You will laugh, you will cry, you will re-watch it over the years and enjoy it every time. Sitcom television, with the exception of Community, just doesn't get better than this.
Thank you for reading! Next week's Tuesday is Halloween, and I have quite a special horror marathon planned, so next week's post will be a recap of that (in the form of a top 10 list, obviously).
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