When Brooklyn Nine-Nine aired their very first Halloween-themed episode in season 1, they unknowingly started a great trend and tradition that would be repeated every season due to the extremely positive response it received from the dedicated fanbase.
This quirky police sitcom is unique for many reasons, and one of them is the fact that they take their holiday episodes very seriously. Including the Halloween specials, Brooklyn Nine-Nine airs multiple other holiday-themed episodes every season, and everyone loves them for it.
The chemistry and lovable dynamics between the Nine-Nine gang mean that the writers of this sitcom are given lots of room to get creative with the misadventures their characters embark on in every episode. The Halloween Heists had a humble start in season 1, but the episode format became more popular than anyone initially imagined it would, and now the show is pretty much obligated to stick to the tradition.
Jake started the Halloween Heists as a way to try to get Holt to loosen up a little and have some fun. This worked and also brought out the captain's competitive side. Throughout the seasons, all the other characters have joined in on these extremely fun, entertaining, sometimes even mindbending heists.
Let's take a closer look at every Halloween Heist from each of Brooklyn Nine-Nine's seasons.
6 HALLOWEEN IV (SEASON 4, EPISODE 5)
The Halloween Heist from Brooklyn Nine-Nine's fourth season is actually regarded as the worst one. The episode wasn't really bad, but it seemed to fall short of the ones that preceded it. Every heist is iconic, but this one tended to feel a little lackluster to the fun that was had in the past. In Halloween IV, the detectives vie for the title of Ultimate Human Slash Genius, and things get intense pretty quickly.
This episode is full of signature Brooklyn Nine-Nine silliness, and a complete unabashed wackiness that only this show can pull off. Beginning with Jake almost killing Scully with an airhorn and ending with Gina ultimately winning the much fought-for title, this episode proves that even a "bad" episode of Brooklyn Nine-Nine is still super fun to watch.
5 CINCO de MAYO (SEASON 6, EPISODE 16)
Cinco de Mayo is the most recent Halloween Heist to take place at the precinct, and it's also the only episode of its kind to be named something other than "Halloween". Overall, Cinco de Mayo was a great episode, but due to the fact that it felt a little different than the past Heist episodes, it's not many fans favorite Halloween special.
This season 6 episode primarily focuses on Terry's upcoming lieutenant's exam and his fears surrounding this big milestone. This is an important plot, of course, so it kind of took away from the usual light-hearted fun that the Halloween Heists typically provide. Still iconic, though.
4 HALLOWEEN, PART III (SEASON 3, EPISODE 5)
Halloween III was an action-packed, completely fun thrill-ride. Since it takes place in season 3, Holt and Jake are the main players, which allows some other characters to sneak up on them and join in the Heist fun. Like every Halloween episode, Halloween III provides all the insane tricks and hilarious gags that make audiences love this tradition so much.
Jake and Holt split the squad into two teams, and everyone is dragged into the fun, even unwillingly. Halloween III primarily follows one main plot, and it does this so well. This show can have one focus for an entire episode and nail it completely.
3 HALLOWEEN 2 (SEASON 2, EPISODE 4)
In season 2, Brooklyn Nine-Nine was still finding its footing and developing its main characters. Relationships were forming and dynamics were being fleshed out, and since everything was still so new, the success of Halloween 2 is pretty impressive. Brooklyn Nine-Nine has always been somewhat of an underrated gem, and this was particularly true in the early seasons. In season 2, this series still had a whole lot to prove.
Halloween 2 revolves around the second annual Nine-Nine Halloween Heist. At this stage, the Heist was still portrayed as an intense bet between Holt and Jake that gets taken to new, crazy extremes. This Halloween episode covered a lot of new ground and worked to further flesh out Jake and Holt's dynamic. As the two vie for the title and Jake insists that he can steal Holt's watch by midnight, we are also treated to some fun with Gina and her dance group, Floorgasm.
2 HALLOWEEN (SEASON 1, EPISODE 6)
The very first episode to spark the trend of the beloved Halloween Heists will forever be iconic. It was definitely the most simple episode, as it begins with Jake attempting to prank Holt by taking his Medal of Valor from his office. Holt is the unwilling participant in Jake's typical antics.
This episode's plot was Jake betting the rest of the precinct that he could steal Holt's Medal. He eventually recruits everyone to help him, and once Jake is the ultimate winner, Holt's competitive side is revealed and the later episodes slowly morphed this elaborate prank into an all-out heist.
1 HALLOWEEN (SEASON 5, EPISODE 4)
The fifth Halloween episode will forever be iconic and will always hold a very special place in fans' hearts. This was no ordinary Heist, as Jake put a beautiful spin on it. The episode is chock-full of fun twists and turns and absolutely hilarious moments, but it's also one of the most emotional episodes of the series.
This episode was pretty close to perfection, from Jake making a bunch of Handmaid's Tale cosplayers infiltrate the precinct to Amy being the ultimate winner. When she finds the object everyone is searching for - a cummerbund - Jake encourages Amy to read the inscription, which says, "Amy Santiago, will you marry me?" This episode is undoubtedly one of Brooklyn Nine-Nine's best, and it is definitely a tearjerking experience.