Best Brooklyn Nine-Nine Halloween Heist Episodes Ranked

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In this article, we rank the best Halloween Heist episodes of Brooklyn Nine-Nine in chronological order. Now Brooklyn Nine-Nine is has people talking about it as one of the best comedy sitcoms of the decade, maybe of all time. The show effortlessly blended great comedy, stakes and serious topics to become one of the most loved shows ever. Not to mention the sheer amount of catchphrases and references it spawned, to the point where most people have quoted the show and not even realized it. Also, the lack of a laughter track, very common in US sitcoms, only enhances the hilarity of the jokes created by Michael Schur, Dan Goor and the talented cast. 


The show follows a police precinct in Brooklyn, New York and the wacky adventures they get up to whilst doing police work. The cast is a who’s who of comedic actors from Stephanie Beatriz’s silent badass Rosa to Terry Crews playing a muscled up police sergeant, Terry Jeffords. All of the cast made the show one of the most sitcoms of the last decade, especially given the variety of characters. But, what is the best part of Brooklyn 99? How much the characters feel human and relatable. Underneath all the ‘Noice’ and ‘Toits’, every episode has an emotional core that drives it along. Highlights include Rosa coming out to the squad, Holt being gay without it defining his character and many more.

Back to the topic of this article, the Halloween Heist episodes were often the best of a season due to the insanity of the heists. Whether it was Terry using a dog to steal a bracelet or Jake crashing through a ceiling, the Heist normally guaranteed madness. Whilst the episodes are remembered for the stunts, they also featured great character development, especially Jake and Amy.

In this regular feature, we take a look at the top editions of a particular TV programme. And so today, we’re picking the best Halloween Heist episodes of Brooklyn Nine Nine. So, what tops our list? Read on to find out!

Best Brooklyn Nine Nine Episodes

7. Season 6 – Cinco De Mayo

One of the main reasons this heist ranks last is it’s not set on Halloween. As the title suggests, this heist is set on the 5th of May so it comes in last kind of by default. That isn’t to say that the episode doesn’t have great moments or twists because it does in abundance. Highlights include the running gag of who is a two time heist winner between Amy and Holt and Kevin participating for the first time. This episode also fully embraces the wackiness of the heist, especially seen when Terry slowly turns everyone against each other prior to the heist. Truly, a supervillain in training. Anyway, whilst the episode is funny, I can’t in good faith rank it above last place. Sorry, Terry….

6. Season 1 – Halloween

Next up in the Halloween Heist rankings is the episode that started the Heist as a series tradition: Halloween. Unlike later series, this task is remarkably simple in practice: Jake has to steal Holt’s medal of honour by midnight. Whilst this is the original, it just doesn’t hit the same heights as later heists which is fairly understandable as it was just the sixth episode ever. That isn’t to say that there aren’t highlights because this episode lays the groundwork for relationships that last across the series. This is true in the case of Jake’s desire for Holt to be the father figure he couldn’t have growing up. So wholesome. For what it achieved, Halloween is a good introduction to the heist for new viewers but not a great heist on its merits.

5. Season 2 – Halloween II

Finishing narrowly above the original in the Halloween Heist rankings is the second Heist. The reason I haven’t put it higher is: the winner was never really hard to guess. After losing the original heist, Holt gets his win back with the help of the rest of the Brooklyn 99 squad. That is not to say the episode does not have funny moments with Holt’s plan being put together well. Like all the best plans it’s wacky and over the top and pays homage to Ocean’s 11. Speaking of that film, this is the first heist to really ramp up the Ocean’s homage, though the first heist might have something to say about that.

The shot of Holt revealing the squad betrayed Jake to see him humiliated is a brilliant reveal and this has definitely helped influence future heists. Why? Simply it nails the dynamic of the Brooklyn 99 squad on Halloween, where anyone can turn at any time, kind of like Pirates of the Caribbean. To conclude this entry, Halloween II is a good episode but not quite as good as the remaining heists. 

4. Season 4 – Halloween IV

This heist really started to ramp up the insanity with a surprise winner in the form of Gina, Holt’s assistant. This made up for the previous heist’s obvious winner with a shock one and a great reveal. The reveal in question centres around Gina’s false teeth which she deliberately knocked out to make it seem impossible that she could win yet she does. The reveal also cleverly references Holt’s reveal in season 2. Other highlights of this heist include Amy and Rosa bonding, the introduction of Bill (Charles’ ‘Doppelganger’) and the iconic Gina knows best jumper. Truer words have never been spoken in a Halloween heist (except one but I’ll get to that…..)

3. Season 3 – Valloweaster

Now look, I might be a hypocrite by including this amongst the best Halloween episodes of Brooklyn Nine Nine. But even I can push aside the ill-fated timing of this episode, damn it NBC! You had one job…. . Anyway, this entry on the heist ranking once again delivers on the customary insanity that makes a heist. The winner this time out was Rosa, depending on your view of heist winners the only 3x winner? Anyway, this heist was ridiculous, especially the montage of Cheddar, Holt’s dog, running but who am I to complain? But unlike Cinco De Mayo, this heist does have a connection to Halloween. The connection in question? The heist keeps getting new timings for comedic purposes until Easter thus it’s still a ‘Halloween’ Heist, maybe?

2. Season 3 – Halloween III

Coming in at number 2 on the Halloween Heist rankings is the third Heist. This is the first one not won by Holt or Jake? Who could have won it? Spoiler it’s Amy, the one other person in serious contention. Shocker…. This heist was good as it was the first since Jake and Amy get together and plenty of hijinks occur. Mostly around Amy’s chest. The running gag involves Holt and Jake thinking Amy has a microphone on her chest. She doesn’t but the joke still stands.

The episode also features Holt and Jake being too reluctant to pick Amy on their teams. Why? Because they both think she’s a double agent. This is a great girl power moment without it being a girl power moment. I know that seems confusing but I’ll elaborate. Because she was written off, Amy is able to use Holt’s fear of her. She also uses Jake’s failure to win the heist. So when she is revealed as the winner it shows the only side she’s on is her own as she wins it undercover. Albeit with the help of a cackling witch. Seriously.. To sum up this heist is a very solid one but there is one heist that triumphs over it.

1. Season 5 – HalloVeen

And at number one for the best Halloween episodes of Brooklyn Nine Nine is HalloVeen. This is mainly because of the most wholesome proposal in TV history: Jake proposing to Amy. Whilst this heist doesn’t officially have a winner, that doesn’t stop madness ensuing in the 99th as usual. But truly the reason I’ve ranked it at Number One is the emotional core of the episode. The core shows how despite it being sappy as hell it hits you right in the feels every time. Nevermore so does the show emphasise how the characters are emotional because they are human.

This works even better given the squad’s competitive and crude approach on Halloween. Besides the proposal and emotional beats, HalloVeen features a truly great subplot about Jake and the mysterious company Nutriboom. Spooky stuff indeed. To conclude my thoughts on HalloVeen, the fact the writers made a satisfying payoff to a relationship without undercutting the emotional core is brilliant. Damn, I’ve become sappy.

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So, those are our thoughts on the best Halloween Heist episodes of Brooklyn Nine Nine! But what do you think? Let us know by leaving a comment below!