The Halloween Heists of Brooklyn Nine-Nine were some of the absolute highlights of the show's eight-season run. This tradition started with a simple episode: Jake Peralta challenges Holt to a bet, saying that he can steal anything that the Captain is protecting. From there, the contest involves the whole cast, with different winners coming out on top in each episode.

Starting in season one and ending with the final episode of the entire show, the heists were a staple of the workplace TV comedy that grew and evolved as the cast changed and developed. They became more complicated and intricate as each character had a chance to plan double-crosses or elaborate cons to get themselves whatever items were selected to be stolen. What's more, many of the most important character-defining moments of the show happened during these heists.

Like many other Micheal Schur comedies, Brooklyn Nine-Nine proves you don’t have to have a death grip on a specific status quo for a sitcom to be popular and enduring. Characters can and should change. While elements of the heists remain the same, these heists often show how much our characters have changed.

8 Season 1: "Halloween"

Brooklyn Nine Nine Halloween Season 1
NBCUniversal

In this season one episode, Jake spends Halloween trying to steal Holt's medal from him, as the two have a bet going on that Jake cannot do so before midnight. The first Halloween Heist is still a great episode, but it isn't as complex and intricate as the others, and so it can feel a bit less exciting by comparison. However, at the same time, if you are marathoning these episodes, it is essential that you watch this one first, as you will see how the heists have escalated with time. It's also missing some twists and turns of later heists, like the betrayals and the gimmicks. This heist is the episode that spawned the entire tradition and is an excellent episode of Brooklyn Nine-Nine, like all the heist episodes are, it just isn't as flashy as the others.

Related: Here's What Makes Brooklyn Nine-Nine a Groundbreaking Comedy Series

7 Season 6: "Cinco de Mayo"

Brooklyn Nine Nine Cinco De Mayo Season 6
Via NBC

The "Cinco de Mayo" heist, as the last Halloween Heist was canceled, sees Terry Jeffords outwit all the other detectives on what seems at first to be an impromptu heist, but really one being manipulated by Terry himself. It's fun to see Terry get a win in a Halloween Heist, since he often ends up sitting them out or pretends to sit them out. Though Gina began the "pretend to be injured and then win the heist plan," Terry perfected it in this episode, as he manages to get the precinct to carry him to an exam he already had while pretending to be unconscious, just so he can give his victory speech. This episode is a solid baseline for heist episodes in Brooklyn Nine-Nine.

6 Season 4: "Halloween IV"

Brooklyn Nine Nine Halloween IV Season 4
Via NBC

"Halloween IV" is the episode where Gina manages to steal a plaque while fooling everyone else with three identical copies of it. This episode is a great showcase of Gina Linetti, especially during the reveal at the end. One clever twist from the episode was that Gina actually didn't break her teeth while falling; instead, she had previously broken her teeth in the fourth grade, and now has false teeth. The partnerships remain stable with no major twist betrayals, save for the one where Gina steals the win from under everyone while on Jake's team, and those pairings are actually quite fun. We get Rosa and Amy, who are both always fun to see interacting together, and Charles and Holt, who rarely get to share a plotline.

5 Season 7: "Valloweaster"

Brooklyn Nine Nine Valloweaster Season 7
Via NBC

Like "Cinco de Mayo," "Valloweaster" has the distinction of being one of the few Halloween Heist episodes not actually occurring on Halloween. In this episode, Rose Diaz manages to trick the 99 into holding the Halloween Heist three times, using each opportunity to steal the item the gang are trying to grab on each day. "Valloweaster" is perhaps the most elaborate of the heists before the series finale heist, with Rosa winning the heist on three separate days. She did so during an episode, where each of the Brooklyn Nine-Nine detectives that competed were handcuffed to their partner, which is all the more impressive when you consider the fact that she was handcuffed to Scully and then a filling cabinet.

4 Season 2: "Halloween II"

Brooklyn Nine Nine Halloween II Season 2
Via NBC

"Halloween II" proved that the Halloween Heists were not going to be a one-off episode gimmick. Once again, Holt and Peralta go head-to-head, but this time Holt pulls out the win by sussing out Jake's plan before he can put it into motion. The episode takes the original Halloween Heist and one-ups the twist, showing Peralta's plan and how Holt sabotaged it. While the original Halloween Heist could have been predicted, "Halloween II" might have been the hardest twist to see coming of these heists. The normal tradition of the heist hadn't been established yet, so audiences didn't necessarily know the pattern of each heist having a character winning when they seem the least likely to come away with the win.

Related: Why Brooklyn Nine-Nine Has One of the Best TV Finales Ever

3 Season 3: "Halloween Part III"

Brooklyn Nine Nine Halloween Part III Season 3
Via NBC

Season 3's "Halloween Part III" is also another one of these heists most likely to have surprised audiences as, before now, we didn't know that the contest of the Halloween Heists would be open to be won by characters other than Peralta and Holt. Ultimately, Amy Santiago manages to take the win after being dismissed by both Holt and Peralta as an agent of the other's side. This episode was quite important in the context of the heists because it showed how they could be opportunities for characters other than Holt and Peralta, who often are shown as competent and smart, to be able to come up with ingenious schemes. It also reinforces that Amy is her own woman, able to exist outside the context of either Jake or Holt's character, and do her own thing. It also established Heist Amy, whose competitive side is a fun fixture of future heists.

2 Season 5: "HalloVeen"

Brooklyn Nine Nine HalloVeen Season 5
Via NBC

"HalloVeen" manages to stand out in the context of Halloween Heists because it ends with a unique twist. No one technically "won" the heist, but Peralta used it to propose to Amy, which was a win for the two of them. "HalloVeen" showcases how these characters have changed and matured over time, with Jake forgoing the personal glory of winning the heist and trying to instead plan a proposal to Amy. We also see Charles, in a rare move, try to strike out on his own, betraying Jake in the process. Everyone also feels less like they're in control, which is good for making a Halloween Heist feel different, as often it's one person manipulating things behind the scenes in ways they'll explain with a smug flashback.

1 Season 8: "Last Day"

Brooklyn Nine Nine Last Day Season 8 Finale
Via NBC

The two-parter "Last Day" is less a Halloween Heist in the traditional sense and more a way to explore how the show and the characters have grown in eight seasons during a Halloween Heist. In a bit of synchronicity between creators and characters, Jake is trying to make the heist the perfect send-off as he plans to leave the 99 while the people making the show also have to deliver a satisfying conclusion to this eight-season comedy. The latter succeed in their aims, while Jake struggles and finds his plans for a perfect goodbye unraveling towards the end, as they come to the same conclusion Jake does. That the bond between everyone in the show lives beyond their relationship as co-workers in the 99, and the episode ends with Jake showing up unannounced to a Terry-run precinct to challenge him to another Halloween Heist. This perfect ending aside, this heist has all the staples. Twists and turns, surprise reveals and plenty of backstabbing. It's fair to say this finale is one of the best on TV.