The Definitive Ranking of Brooklyn Nine-Nine's Halloween Heists

7. The Humble Beginnings: Halloween

Kicking off our list is the episode that started it all: Season 1’s 'Halloween.' This inaugural heist laid the groundwork for what would become a beloved tradition. With Jake ambitiously challenging Holt to a Medal of Valor theft, the episode tantalizes with its simplicity and raw charm. Despite its predictability, the finale where Jake triumphs is a testament to the show's evolving wit. The episode's success is not just in the plot but also in establishing the team dynamics that would be pivotal in future heists.

Holt, Peralta, and Santiago in the office with Halloween decorations in Brooklyn 99

The episode's humor fused with a competitive spirit set a high bar for subsequent seasons. Jake's initially pathetic attempts at theft, which are later revealed to be a clever ruse, demonstrate the series' signature blend of humor and cunning. This episode also marks the beginning of the Jake-Holt rivalry, adding a layer of depth to their relationship that fans have come to adore.

Holt and Jake face to face during a Halloween Heist

Although 'Halloween' may not have had the complexity of later heists, its significance in the Brooklyn Nine-Nine universe is unassailable. It's a classic case of starting small and growing into something legendary, much like the series itself. This episode not only provided laughs but also laid the foundation for the heist tradition, making it a fitting entrant on our list.

Holt, Jake, and Amy talking in a podium in Brooklyn Nine-Nine

6. The Start of a New Era: Halloween II

Season 2's 'Halloween II' takes the sixth spot, building on the dynamics established in the first heist. The episode is a fascinating exploration of the evolving relationships within the squad, particularly between Jake and Holt, who are both hell-bent on outsmarting each other. The involvement of the entire team, albeit in a more passive role than in later heists, adds a communal aspect to the rivalry.

Jake and Holt after the Halloween Heist.

One of the episode's strengths lies in its ability to balance character development with the thrill of the heist. The detectives’ choice to side with Holt to humble Jake is a sharp turn of events that enriches their interplay. The episode also cements Holt's investment in the heists, which is crucial for the comedic gold that ensues in future seasons.

While 'Halloween II' does not carry the same shock value as some of its successors, it is a pivotal chapter in the saga. It is an impressive feat for a second-season episode to handle the weight of expectation following a successful premiere and still manage to deliver, making it deserving of its rank on our list.

Jake looking worried in Brooklyn Nine-Nine

5. The Underdog's Victory: Halloween III

At number five, we have 'Halloween III' from Season 3, which takes an interesting turn by sidelining Amy from the main event. This decision ultimately leads to a rewarding payoff when she emerges as the mastermind behind the heist. The episode excels in subverting expectations and showcases Amy's growth from a sidelined character to a cunning competitor.

Jake crowns Amy after the Halloween Heist

The episode also marks a shift in the structure of the heists, with the introduction of team-based strategies. This evolution in the heist format keeps the narrative fresh and sets the stage for more complex plots. Amy's unexpected victory over both Jake and Holt is a delightful twist that reinforces the show's penchant for empowering its characters in unexpected ways.

Jake looks at Amy wearing a crown

While the ending reveal may not have been as unpredictable as intended, 'Halloween III' still stands out for its character development and the significant role it plays in the series. Amy's win is a pivotal moment that pushes the boundaries of the Halloween Heist episodes and secures its middle-of-the-pack ranking.

Amy in the precinct in Brooklyn 99

4. The Ingenious Comeback: Cinco De Mayo

Season 6's 'Cinco De Mayo' cleverly adapts the heist tradition to fit within a new holiday, demonstrating the show's ability to innovate under constraints. We place it at number four for its ingenious approach to storytelling. Terry's unexpected master plan, which involves using Cheddar and manipulating the squad, is a high point for his character and showcases his often-understated cunning.

Terry painted in bronze yelling at Jake

This episode also reflects on the growth of the characters and their relationships. Terry's reluctance to participate in previous heists contrasts sharply with his deep involvement here, offering a refreshing character arc. The heist being interrupted by emergencies adds layers of realism and tension, emphasizing the show's knack for blending the absurd with the authentic.

All the characters on an elevator in the Brooklyn Nine-Nine Finale

The 'Cinco De Mayo' heist is a testament to Brooklyn Nine-Nine's commitment to keeping the series dynamic, even in its later years. The episode's blend of humor, unexpected twists, and character development are the reasons it earns a solid spot in the upper echelons of our ranking.

Jake, Amy, Gina and others look through a hole in the wall

3. The Emotional Rollercoaster: HalloVeen

The third-best heist, 'HalloVeen' from Season 5, is perhaps the most emotionally charged episode of the bunch. This heist goes beyond the usual antics and delivers a heartwarming moment that cements Jake and Amy's relationship. The episode is packed with fun and suspense, but it's the touching proposal that elevates it to a new level, making it unforgettable for fans.

Jake proposes to Amy in Brooklyn Nine Nine's HalloVeen

With clever diversions, including Handmaid's Tale cosplayers, and Amy's intelligent maneuvers, the episode maintains the series' comedic and strategic standards. However, it's the blend of romance and rivalry that gives 'HalloVeen' its unique charm. It's a heist that manages to balance laughter with love, a combination that resonates deeply with audiences.

Jake and Amy proposal in Season 5, Episode 4

While there may not be an official 'winner' due to the proposal, the episode's significance in Brooklyn Nine-Nine history is indubitable. It's a narrative achievement that demonstrates the show's range, proving that it can deliver both hilarity and heart in equal measure. This is why 'HalloVeen' steals the third spot on our list.

People dressed as Handmaid's Tale characters in the 99th precinct

2. The Game-Changer: Halloween IV

Securing the runner-up spot is 'Halloween IV' from Season 4, where the heist takes an unexpected turn with Gina's triumphant reveal as the Ultimate Human/Genius. This episode is pivotal as it broadens the scope of potential victors beyond the detective realm. Gina's win, despite her apparent incapacitation, is one of the greatest misdirects in heist history, reshaping future contests.

Amy and Rosa look at Gina from behind a door in Brooklyn 99

The episode's brilliance lies in its seamless blend of high-stakes competition and outright hilarity. Gina navigating through the heist with a setback adds a layer of intrigue and humor, while the inclusion of Cheddar and body doubles heightens the comedic element. The stakes are palpable, and the twists are perfectly executed.

Jake yells at Amy's chest in Brooklyn Nine Nine

What sets 'Halloween IV' apart is how it redefines the competition, opening doors to new possibilities and setting a precedent for inclusivity within the heist narrative. It's a game-changer that adds depth and diversity to the event, earning its place as the second-best Halloween Heist episode.

1. The Ultimate Farewell: The Last Day

Topping our list is the series finale, 'The Last Day,' a two-part episode that encapsulates the essence of Brooklyn Nine-Nine. The final heist is not just a culmination of wacky antics and unforeseen twists; it's an ode to the characters we've grown to love. Hitchcock's accidental win is a fittingly humorous and surprising end to the heist saga, and Jake's emotional departure adds a layer of sentiment to the series' conclusion.

The final "Nine-Nine!" chant in Brooklyn Nine-Nine

This episode is a celebration of the journey, packed with callbacks and nods to the show's memorable moments. The reunion a year later is a poignant touch, illustrating the enduring bond among the characters. The heist serves as a backdrop for a larger narrative about change, growth, and the bittersweet nature of goodbyes.

The reason 'The Last Day' takes the crown on our list is the balance it strikes between honoring the past and embracing the future. It captures the spirit of camaraderie, the thrill of the chase, and the emotional weight of the series finale beautifully. It's not just the best Halloween Heist; it's a masterful sendoff to a beloved show.

Jake and Holt sitting in the precinct and talking in Brooklyn Nine-Nine finale