Brooklyn Nine-Nine: Every Single Halloween Heist Episode, Ranked

In the first season of Brooklyn Nine-Nine, we were introduced to the Halloween Heist, a bet that started between Captain Holt (Andre Braugher) and Detective Jake Peralta (Andy Samberg) on Halloween.

Jake bet Holt that he could steal the captain’s medal of valor. If successful, Captain Holt would be responsible for completing Jake’s paperwork for the evening and publicly calling the detective an “Amazing Detective/Genius.”  Eventually, the entire squad ended up taking part in the battle of wits and the Halloween Heist episodes of Brooklyn Nine-Nine became a fan favorite.

Each season came up with a new version of the hilarious competition. While each Halloween Heist episode is funny in its own way, there are definitely some Halloween Heist episodes that are better than others.

In honor of Halloween, here is every single Brooklyn Nine-Nine “Halloween Heist” episode, ranked.

8. “Valloweaster”

Season 7, Episode 11

“Valloweaster” had to air after Halloween due to the series being temporarily canceled but later picked up by NBC. To cope with the timeline disruption, season 7’s Heist took place across several holidays including Halloween, Valentine’s Day, and Easter.

While this was definitely a clever solution, eventually the bits throughout this particular episode did get a little stale and predictable. Rosa Diaz (Stephanie Beatriz) ended up winning this Halloween Heist.

7. “Halloween III”

Season 3, Episode 5

Next up, “Halloween III.” In the third Halloween Heist, Jake and Holt faced off once more to determine who is the ultimate detective slash genius. In this iteration of the contest, Captain Holt and Jake divided up the squad between them both to help them on their mission. Well…the entire squad except Amy Santiago (Melissa Fumero). Also, Hitchcock and Scully, but that’s not entirely surprising.

Anyway, it’s in the third season that Jake and Amy finally began dating, which is why she as left out of the Heist. Holt figured he couldn’t trust her given she is Peralta’s “paramour.” Jake determined he couldn’t trust his girlfriend because of her dedication to her mentor.

This is where they made a grave mistake, as Amy ended up swooping in to win the Heist with a carefully devised pan to not only humiliate Holt and Jake but to also prove that she is her own person, capable of making her own decisions.

6. “The Last Day”

Season 8, Episode 9-10

It only made sense for Brooklyn Nine-Nine‘s final episode to be a Halloween Heist. The only reason this episode is further down on the ranking is because I was so devastated the show was over.

That said, the two-part Halloween Heist episode is so incredibly wild, hilarious, and deeply heartfelt. Oh, and somehow Hitchcock (Dirk Blocker) wins.

5. “Halloween II”

Season 2, Episode 4

The fifth best Halloween Heist episode is the second version of the competition. After Jake was victorious over Captain Holt in the first season, Jake challenges Holt to another heist. When Holt waffles over whether or not he’s interested in competing against Jake again, Jake says he will quadruple his overtime if Holt wins. Holt agrees.

This time, the object to steal is Holt’s watch. Jake hires a skilled pick pocket named “Fingers” to help him snag the timepiece off of Holt’s wrist. Of course, this wasn’t the best decision, as Fingers takes off with the watch, only saying he’ll give it back if Jake gives him $200. Jake agrees, to which Finger reveals he never had the watch and simply conned Jake out of his money.

From there, things only get worse for Jake. It seems as though at every single turn, something goes wrong. And it did by design. Because at the end of the episode, it’s revealed that Holt had been planning his comeback since the previous Halloween. He recruited the rest of the squad to help him find victory (and embarrass Jake).

4. “Halloween IV”

Season 4, Episode 5

Season 4’s Halloween Heist is hysterical. After Amy snagged a win in Season 3, she joins Holt and Jake as champions. This time, the three are competing to steal a plaque that reads “Amazing Detective/Genius.”

The three Heist champs select their teammates for the heist. Amy teams up with Rosa. Holt, surprisingly, chooses Charles Boyle (Jo Lo Truglio) to be his partner, leaving Jake to pair up with Gina (Chelsea Peretti). Holt selected Charles as a strategy to ruin Jake’s plans, as he figured Jake would have gone with his best friend had he the option.

(Sergeant Terry Jeffords, played by Terry Crews, sat this Halloween Heist out. But more on that later.)

Anyway, Holt was right because Jake hired a random guy off the streets of Brooklyn who could be Charles’ twin as part of an elaborate plan to win. Another crucial component of Jake’s planning involved rollerskating, something Charles excels at doing. After Gina convinces Jake to let her take Charles’ place, things turn disastrous after Gina runs into a wall while skating and knocks out her two front teeth as a result.

Gina ends up going to the dentist for her injury, which means Jake is stuck with Fake Charles to try to score a victory. As the fourth Halloween Heist continues on, it’s hard to keep up with who has the plaque. Towards the end of the night, all three teams come together, each holding a plaque. Suddenly, black lights turn on, revealing a message for the reigning champs to put together: “Heists are dumb.”

Immediately, everyone suspects Terry and runs to the interrogation room to corner him. However, in a major twist, the squad gets locked in by Gina, who was fine the whole time and planned the skating accident so she could win but more importantly, change the name of the champion from Amazing Detective/Genius to “Amazing Human/Genius.”

3. “Halloween”

Season 1, Episode 6

The first Halloween Heist is absolutely one of the best. Jake bet Holt he could steal the captain’s medal Of valor from his office. If Jake was successful, Captain Holt would be in charge of completing all of Jake’s paperwork for the evening and publicly stating that Jake was “Amazing Detective/Genius.”

Throughout the episode, Jake fails over and over and over again in many hilarious ways. Eventually, Jake and Holt find themselves face-to-face at the end of the night after Jake is arrested by some uniformed officers for scaling the side of the building with a blow torch.

As it turns out, this was all according to Jake’s plan. While his first attempt to steal Holt’s medal was a true failure, he then bribed the rest of the squad with the promise to do their paperwork if they helped him defeat Holt. And together, they did.

This Halloween Heist is great not only because it’s the first but also it was the first time we started to see Holt’s personality come out more and his competitive side. And, most importantly, it was when a real bond began to form between the new captain and his detectives.

2. “Cinco De Mayo”

Season 6, Episode 16

In my oh-so-humble and completely correct opinion, the second best Halloween Heist episode is in season 6. The sixth Halloween Heist takes place on Cinco de Mayo, which also coincides with Sarg’s 5 PM lieutenant’s exam. Terry hates tests, so Jake proposes the squad does a Cinco de Mayo Heist to distract Terry from his nerves.

From there, the usual chaos and betrayals ensue as everyone takes everything way too far, including Terry getting knocked out cold by a sign Jake bought that reads “All Hail King Jake.” As the squad rushes to get Terry to his exam on time, it becomes more and more clear Sarg isn’t fit to take the test.

When Jake goes into the classroom to let the test practitioner know Terry wouldn’t be taking the exam, only to be met by a completely empty room. As everyone stands around perplexed, Terry, perfectly fine and without a concussion, reveals that he not only already had taken the exam weeks ago and passed, but also was in possession of the medical alert bracelet they had been competing to steal.

Terry winning was surprising and hilarious, especially given his biggest teammate was Holt and Kevin’s dog Cheddar, which gave us one of Holt’s most iconic lines:

“Cheddar, you duplicitous bitch.”

1. “HalloVeen”

Season 5, Episode 4

And, finally, the best Halloween Heist episode has to be Season 5’s “HalloVeen.” After Jake and Rosa were framed for a slew of bank robberies in season four and sent to prison as a result, the two are eventually proven innocent and released at the beginning of season 5.

The stakes were high as the squad competed to be declared an Amazing Human/Genius. This time, they were aiming to steal a championship belt (or cummerbund, as Holt calls it).

At the end of the episode, it’s just Jake and Amy alone in the evidence room, where Amy finds the belt right at midnight. However, when she goes to read the inscription on it, it says:

“Amy Santiago, will you marry me?” And from there, Jake proposes. And Amy says yes. It’s an incredibly sweet moment.