Summary

• The Halloween Heists in Brooklyn Nine-Nine have become a beloved tradition, with unexpected twists and surprising winners every year.
• Each Halloween Heist episode keeps things fresh and unique by involving more characters and upping the ante.
• The Halloween Heists have had memorable moments, from Amy becoming a mastermind to Terry orchestrating a plot using Cheddar and department members.

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. The Halloween Heists had a humble start in season 1, but the episode format became more popular than anyone initially imagined it would, and the show became obligated to stick to the tradition.

What helped make the Halloween Heists so fun was how Brooklyn Nine-Nine always found a way to keep things fresh and unique. Jake vs. Holt was fine on its own but seeing Amy, Rosa, and even Gina (who isn't even a detective) get involved only added to the fun and upped the ante. With unexpected twists and turns in each episode, every Halloween Heist was won in surprising fashion, making it the series' most anticipated episode annually.

Watch on Peacock

8 Halloween III

Season 3, Episode 5

Since this took place in season 3, Holt and Jake were the main players and the stakes were high since they were tied 1-1 entering the year. Like every Halloween episode before and after "Halloween III" provides all the wild tricks and hilarious gags that made audiences love this tradition so much. However, the twist this time was that Jake and Holt split the squad into teams, only to leave Amy out.

Being shunned by her boyfriend and mentor stung Amy to the point where she became a mastermind of her own. While it was a great twist to see Amy get directly involved and defeat both Holt and Jake, the reveal at the end felt a bit too telegraphed to really stick the landing. That said, Amy actually being a detective/genius made it a fitting title for her.

7 Valloweaster

Season 7, Episode 11

Season 7 of Brooklyn Nine-Nine faced a problem in delivering one of its beloved Halloween Heist adventures, as the season didn't begin until after the holiday due to the series being canceled and then brought back. However, they managed to find a clever and fun to work around that with the heist going so off the rails that it spans several holidays. It was exactly the kind of twist the show needed with the formula.

Fitting with the times, a play on Thanos' Infinity Gauntlet was what needed to be stolen here. The episode played the hits of the Halloween Heists with callbacks like bringing in Charles' body double. However, by this point in the series, only Rosa and Charles had yet to win so Rosa's win, while well done, wasn't all that surprising, and surprises are a big part of what makes these episodes special.

6 Halloween IV

Season 4, Episode 5

In Halloween IV, the detectives competed for the title of Ultimate Detective/Genius, and things got intense pretty quickly. After Amy's win in the third heist, the fourth installment saw her, Jake, and Holt pick teammates. Jake ended up with Gina, who skated into a wall and lost her two front teeth but that was only the beginning of the shocks.

With her out of action, the three detectives continued to try to win, using everything from body doubles to Holt's adorable dog Cheddar. In the end though, Gina revealed that she was behind it all and changed the title to Ultimate Human/Genius. This altered things going forward for the storyline as anyone was capable of being cunning enough to be crowned the winner.

5 Cinco De Mayo

Season 6, Epsiode 16

By the time season 6 rolled around, the show had to switch things up a bit to make these Halloween episodes work. They'd established a formula and already done twists like having a non-detective win and even including a marriage proposal in one of them. To change things up this time, the heist was interrupted several times for various emergencies, leading to a Cinco de Mayo edition.

In past seasons, Terry often didn't want to get involved in the heist antics, even going as far as to say "heists are dumb." Add in the pressure of his upcoming lieutenant's exam and he seemingly wanted not part of this installment either. So, the reveal that Terry was behind a master plan that included using Cheddar and playing the department members against each other was all the more impressive.

4 Halloween II

Season 2, Episode 4

In season 2, Brooklyn Nine-Nine was still forming relationships and dynamics were being fleshed out. Since everything was still so new, the success of "Halloween 2" is even more impressive. At this stage, the Heist was still portrayed as an intense bet between Holt and Jake that gets taken to new extremes. This Halloween episode covered a lot of new ground and worked to further flesh out Jake and Holt's dynamic.

Even with the other detectives not actively taking part in trying to win, the show kept them involved in intriguing ways as Jake got them to help him much like the year before. However, he underestimated them as they all opted to help Holt instead, simply to see Jake be humbled a bit. This was truly the start of Holt being just as invested in the heist as Jake, if not more so, which was always a good source of comedy.

3 Halloween

Season 1, Episode 6

Like many other sitcoms, Brooklyn Nine-Nine took a little while to really hit its stride. Early episodes seemed unsure of how far to take Jake's immature side but it really felt like things started clicking with the inaugural Halloween Heist. This pitted Jake directly against Holt with a simple challenge that Jake could steal Holt's prized Medal of Valor without him knowing.

Jake's attempts to win looked pathetic throughout, causing Holt to question his smarts and even call him out for the poor attempts. Of course, it was all a ruse as Jake had a plan with help from the rest of the precinct to pull off the upset. It showcased the teamwork that ended up as a staple of the series, set the tone for future similar episodes, and proved Jake could outsmart Holt from time to time.

2 The Last Day

Season 8, Episodes 9-10

Whenever a show reaches the series finale, there are always going to be callbacks and nods to what made it special in the first place. For Brooklyn Nine-Nine, there was no better way to end things than to return to one final heist. It included the usual combination of wacky Halloween antics and surprise sequences but had the added heartfelt aspect of knowing this was the end of seeing these characters.

The two-part episode also saw the most shocking winner as Hitchcock was revealed to take the crown. In typical Hitchcock fashion, he had no master plan and kind of just fell into the win. On top of the great twist, there was Jake's emotional goodbye as he was leaving the Nine-Nine and the reunion a year later as everyone returned to keep it up as an annual tradition even after people moved on to other avenues.

1 HalloVeen

Season 5, Episode 4

The fifth Halloween episode will forever hold a special place in fans' hearts. As usual, the episode is chock-full of fun twists and turns but it's also one of the most emotional episodes of the series. This was pretty close to perfection, from Jake making a bunch of Handmaid's Tale cosplayers infiltrate the precinct to Amy seemingly being the ultimate winner.

That's where the best plot twist comes though as this ends up being one of the biggest episodes for Jake and Amy. He turned the final moment of the heist into a touching marriage proposal to Amy, providing one of the sweetest moments in the series. That added emotional aspect makes it the best heist, even if there isn't an official winner. Amy got there first but Jake seemingly wanted that to happen, so the result remained up in the air.

• 

  Brooklyn Nine-Nine

  Release Date:

  2013-09-17

  Cast:

  Stephanie Beatriz, Melissa Fumero, Andy Samberg, Andre Braugher, Joel McKinnon Miller, Dirk Blocker, Terry Crews, Chelsea Peretti, Joe Lo Truglio

  Genres:

  Comedy, Crime

  Seasons:

  8

  Rating:

  TV-14

  Story By:

  Michael Schur

  Writers:

  Michael Schur, Dan Goor

  Network:

  FOX, NBC

  Streaming Service(s):

  Netflix, Peacock

  Showrunner:

  Michael Schur, Dan Goor