Brooklyn Nine-Nine is easily, my second favourite sitcom. It would be number 1, if only that pesky Red Dwarf had never been made (I am not complaining about the existence of Red Dwarf, it is my number 1 favourite sitcom)! I got into Brooklyn Nine-Nine during the fourth season, and just couldn’t stop watching it. It was, is, and will always be one of the greatest sitcoms ever created (but after Red Dwarf of course).
One of the show’s mainly highlights over it’s eight season run (‘IT SHOULD HAVE BEEN 10+…WHY ONLY 8…WHY?’) is of course the annual Halloween Heists. What started out as a plot from one episode in the first season, became one of it’s more anticipated annual presents, as the squad pulled out all the stops to take a coveted title. Over those eight (‘WHY?’) magnificent seasons we saw surprise victories, astonishing moments of deception and trickery, and of course barrel loads of laughter inducing content.
But which is the best Halloween Heist? Which one is the standout master of of all those spooky themed capers. Well, I thought I would share with you which ones were my favourites, ranking them all in a list, with the truly most magnificent of them all waiting at the very bottom of this post (which you could cheat and skip to, ignoring all the other positions and the hard work I put into ranking them all into a written list, if you really want to), just for dramatic purposes. So then, without further ado, here are my Top 8 Favourite Brooklyn Nine-Nine Halloween Heists; Enjoy!
8. Season 1 (Halloween) – Winner: Jake Peralta – The first Heist, always an important point, as if there is no beginning, there is no tradition. The first heist is a good one, as it shows a rather desperate detective trying to prove he can be a great criminal, and desperate to try and defeat his workplace Nemesis. So there’s plenty of chaotic moments, albeit on the small side, and plenty of silly smaller moments too. The first heist though, is not the full focus of the show, as there’s two subplots to connect with. There’s the case of Terry trying to find out one of the many deep secrets of Rosa, and then there’s Charles trying to get Amy to enjoy Halloween. So, Not the greatest Heist, but you can easily see there’s something starting!
7. Season 8 (The Last Day Pt.1 and Pt. 2) – Winner: Michael Hitchcock – Finishing off the final series with a mega Halloween Heist was a terrific idea, and in some ways for this alone it could be considered the best. It features heroic returns from cast members such as Gina and of course Pimento, plus it had some surprising twists and turns along with some good old Joker style anarchy. But, it suffers on two points. Firstly, as it is the final episode, it commits quite a bit of time to wrapping up the show. Due to the decision to make the final season only ten episodes long, it tries to slash and burn the series, and as a result, it’s not a truly satisfying conclusion, it’s just a conclusion. And then it has the wrong person winning it. Yes, it’s a laugh that Hitchcock wins it, but, it really should have been Charles. All these years as a supporting detective, this should have been his crowning achievement as the best detective. Instead we get this continually, and never resolving case of Charles never winning the Halloween Heist… which is just really sad!
6. Season 6 (Cinco De Mayo) – Winner: Terry Jeffords – The first Heist not to take place during Halloween, given the scheduling conflicts due to the show being cancelled by Fox after five seasons, to then be picked up by NBC. So, it’s not on Halloween, but it’s still a festive themed Heist. This one is less chaotic than other Heists, as the contestants try hard to pull off smaller capers without anyone noticing, only for them to be double crossed, by, well…everyone else. But, the chaotic nature returns at the end, as the true puppet master is revealed, who has been pulling the strings of everyone this time, to pull off a well deserved victory!
5. Season 5 (HalloVeen) – Winner: Jake, or Amy, or Captain Holt – This is a weird Heist, given that to this very day, the winner is still disputed. OK, the episode was done as a way to lead up to the big reveal at the end as Jake proposes to Amy, but, due to the amount of onscreen havoc, leading up to this finish does feel a bit lame. But, despite this controversial subject, the episode is a decently fun one, as it cements Cheddar as an integral part of all future Heists, not just a cameo. There’s intrigue, deceptions a plenty, and a mad dash at the end, as the cast reveal their dark side, by placing intrusive (and dangerously unhealthy) devices into one contestant, to gain their desperate edges!
4. Season 3 (Halloween III) – Winner: Amy Santiago – The third Heist feels like the first time where the episode is fully committed to the Heist, and is not sharing the episode with the sub plot. Although there is still some subplot in Gina and Charles’s interactions in the interrogation room. The focus here though is on two warring clans, as they try their utmost to outdo the other, not realizing that their scheming is being watched over by a third party, who uses their ignorance to steal victory from both of them. These two clans were hoping to end it all here, but now, things cannot end, as too many people are becoming involved!
3. Season 2 (Halloween II) – Winner: Captain Raymond Holt – Much like the first Heist, this heist is more or a less still an ordinary episode of the series. But, it is the first time that we see how over the top the heists can become. We still have a subplot outside of the heist involving Gina’s dance troupe, but the Heist still takes the lead in the episode. Holt wins this time around, which is rather ironic given that the amount of hilarity inducing antics he has to do in order to beat Jake, as it against his more professional outlook in both work and life, over Jake’s clowning around. It is the first real taste of what is to come!
2. Season 7 (Valloweaster) – Winner: Rosa Diaz – This Halloween Heist ranks highly for several reasons, but most of all it proves, in a Bret Hart sort of way, that Rosa Diaz is the Best There Is, Best There Was, and the Best There Ever Will Be! The episode starts off in a frantic way, with the entire opening sequence looking like a scene from a mad horror film, with that evil laugh as a bunny jumps off the roof. Then we get three heists in one episode, as the heist keeps getting postponed due to several reasons, mostly involving a vet (who also examines Scully), leading onto the third chaotic edition. But, this was all planned as the winner, had an argument to win, an argument which then continues to her joy, in the process turning her into the Booker T of the squad, as she technically becomes a ‘Five Time, Five Time, Five Time, Five Time, Five Time‘ Halloween Heist Champion!
1. Season 4 (Halloween IV) – Winner: Gina Linetti – The fourth Halloween Heist is the best, because the winner of the contest is so well set-up, and no matter how many time you watch it, it’s still a surprise that Gina wins it. It’s a surprise, because she is taken out of the episode early on with what you believe is a legitimate injury, and you don’t question it. She is no longer in the episode, and therefore out of the competition. But then, BANG! She’s back, she’s won! You thought she had gone, but no, it was all a ruse, planned out by one the most devious (but caring) characters in sitcom history. Seriously, watch it over and over again, and tell me you’re still not shocked at Gina winning it!
Which is your favourite Halloween Heist?








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