The Brooklyn Nine-Nine Halloween Heists: A Ranking

Halloween is upon us. It’s a time for fun, festivities, costumes, partying, and sweets. Since 2014, Brooklyn Nine-Nine has had their traditional Halloween Heist where the squad competes for an item. There were elaborate plots and hijinks, lots of betrayals, and offered some of Brooklyn Nine-Nine’s most memorable moments. It’s a TV Halloween tradition that can stand close to The Simpsons “Treehouse of Horror” segments. So now is a great time to rank the Halloween Heist episodes.

7. Valloweaster

“Valloweaster” was the most recent Halloween Heist episode. This episode saw the heist take place over three holidays: Halloween, Valentine, and Easter. At the start of this heist, the squad gets randomly assigned a partner and tethered to them. Jake and Holt worked together in Jake’s devious plan to win without realising he was manipulated by his wife. Amy worked with Boyle and Rosa was unfortunately lumbered with Scully. However, Rosa won by playing the long game and become the first three-time champion.

“Valloweaster” was bigger in scale and more self-aware due to its references to Cheddar and Bill. The funniest jokes in the episode were Bill’s deteriorating circumstances and everyone stating they love for Cheddar. Rosa’s revealing how she won was also a highlight, especially when she spoke with Scully’s doctor. This was the first episode that Rosa referred to Arlo since “9 Days.” Amy dressed in a pumpkin costume was an obvious attempt to hide Melissa Fumero’s pregnancy, but I like to think it was a reference to the Slutty Pumpkin from How I Met Your Mother.

Whilst “Valloweaster” had funny moments, the decision to split the heist over three holidays made the episode too fragmented. The Valentine’s Day segment was forgettable, and the episode felt more like three mini-stories rather than as a whole piece.

6. Cinco de Mayo

2019’s “Cinco de Mayo” was the first Heist episode to not take place on Halloween. The previous Halloween Heist had to be cancelled due to a gas explosion, so the squad decides to spontaneously hold it on Cinco de Mayo as a way to relax Terry before his Lieutenant’s Exam. What resulted was one of the most bitter and ludicrous heists in Brooklyn Nine-Nine’s history (so far.)

“Cinco de Mayo” aimed to break the mould of the Heist episode by setting on a different holiday. This episode was the Game of Thrones of Brooklyn Nine-Nine due to all the betrayals. Jake betrayed Terry, TWICE, Jake and Amy shocked each other with hidden tasers, and Rosa drugged Boyle and packaged him to New Jersey – luckily Boyle knew how to get out of a box just by getting it wet enough. However, all these betrayals and the elaborate nature of the heist where everything had to go right for Terry.

This was the episode where Terry was painted gold and looked like an Oscar, and my favourite joke was when Jake found out he wasn’t smarter than a dog.

5. Halloween IV

The fourth Halloween Heist was set to be a tiebreaker between Jake, Holt, and Amy who had won the previous heists. In this heist the squad were split up into pairs: Amy and Rosa, Jake and Gina, and Holt screwed with Jake by choosing Boyle as his partner. The heist seemed to get derailed when Gina crashes into a pillar and knocks out her front teeth. However, this was a rouse by Gina so she can win the heist from under their noses. Gina did this because she wanted to end the non-detective discrimination. It was worst than segregation.

In this heist, Gina played the long game to win the heist and her win was combined the strategies that Holt and Amy used to win. Gina sowed the idea for Holt to pick Boyle as his partner and ordered three identical plaques. Whilst like Amy, Gina competed under the radar and worn the drabbest outfit possible, one of Amy’s pantsuits.

The best joke in the episode was the opening when the previous winners announced the heist – Amy’s was dainty, Holt’s was grand, and Jake nearly gave Scully a heart attack. The other great joke was the black light revealing how disgusting the precinct was. I personally enjoyed Amy using The Baby-Sitters Club books as an inspiration and Holt using Cheddar.

4. Halloween II

“Halloween II” saw a rematch between Jake and Holt. In this heist, Jake challenged Holt that he could steal his watch by midnight and if he fails, Jake would work overtime shifts for free. Holt reluctantly agrees. Jake’s plans went awry when the professional pickpocket he hired betrayed him, leading to Jake going on a wild goose chase around Brooklyn. What Jake didn’t realise was Holt had prepared for a year and was one step ahead of his detective.

Holt was able to flip the whole squad to work to help him. Holt annoyed Jake into stealing his watch, hired the pickpocket as a double agent, and used the squad’s skills like Terry’s strength and Rosa’s seductive dancing.

“Halloween II” was the last episode Heist episode to have a B-plot. In this episode, the subplot involved Terry finding out why Gina had been skipping out on her work duties. It turned out that Gina had started attending college and she had been kicked out by her dance troupe because of her studies.

The episode was at its best when Jake and Boyle had to leave the precinct to meet the pickpocket and having to find Jake’s car. It was made even better when Holt revealed how he won the heist, like being on the party bus and who the bears really were.

3. Halloween

“Halloween” was the first Heist episode and set the precedent. In this heist, Jake challenges Holt that he could steal Holt’s Medal of Valor. To win Jake had to distract Holt and got the squad to help him. In exchange for their help, Jake would do all their paperwork, resulting in Holt doing all of Jake’s paperwork.

“Halloween” also had two subplots. The first involved Boyle and Amy going undercover with the pair having different views on the holiday. Boyle loves Halloween whilst Amy called it ‘Christmas for Jerks.’ The other subplot involved Terry asking why Rosa was kicked out of Catholic School.

The episode did play out more like a traditional episode because it had an A, B, and C plot and some jokes made it a time capsule of 2014. One of the set pieces was identifying the Royal Baby who mugged John Ross Bowie (AKA Kripke from The Big Bang Theory) and Jake had to split up Hillary Clinton and Kim Jong-un who were making out in the holding cell. Due to the episode taking place early in the show’s run Holt saw Jake as nothing more than a manchild and underestimated his abilities.

2. Halloween III

I have a soft spot for Amy Santiago and my bias is one of the reasons why her Heist winning episode ranks so highly. The third Halloween Heist was set to be a tiebreaker between Jake and Holt to confirmed who was the true heist winner. The squad was split into two teams but neither Jake nor Holt choose Amy. Holt believed Amy would be too loyal to her boyfriend whilst Jake thought she would do anything to earn Holt’s approval. Amy spited the two of them by setting out to win the Heist, with a little help from Hitchcock.

What made Amy’s win special was she had to come up with her plan on the fly. She had to use all her detective and observational skills to discover what Jake and Holt’s plans were and disrupt them. Her reward was being crowned Queen of the Nine-Nine.

The episode showed how resourceful and quick-witted Amy was. I enjoyed the running gag of people yelling at Amy’s breasts, motivating Amy to win the heist. “Halloween III” had the best Halloween cold opening because the squad trick Boyle into wearing a costume after Boyle decided not to wear one.

1. HalloVeen

Topping the list was the fifth Halloween Heist. The 2017 competition was open to all members of the squad, so making the Heist for the championship cummerbund into a free for all. In the episode Boyle, Rosa and Terry form an alliance known as The Tramps, Amy kidnaps Holt’s dog despite being allergic, and Jake was so desperate to win that he signed up for a multi-level marketing opportunity. All this led to the big moment where Jake proposed to Amy.

“HalloVeen” had the big emotional moment of the proposing and it was a busy episode. The big set-piece was Jake’s Handmaid Tale distraction, and it was a funny episode throughout. Holt got some of the funniest moments in the episode because he had to lie to Scully and Hitchcock about why he’s sweating, and his reaction to finding out Cheddar had been kidnapped. Never get between a man and his dog. Amy had an interesting take on her loving relationship.

The episode had ramifications. Later in the series Jake tried to get bring down NutriBoom, Jake and Amy got married at the end of the series, and during the Cinco de Mayo heist, Jake, Amy, and Holt all claimed victory. Jake proposed, Amy remembers Jake being down on his knees, and Holt found the original cummerbund.