Every Halloween Heist Episode Of Brooklyn Nine-Nine, Ranked

Halloween is a holiday about rituals. Whether you're a wide-eyed little kid trick or treating for the first time, a fan of escaping yourself via elaborate costumes, a horror movie marathoner, or just an unimaginative stick-in-the-mud that enjoys all the leftover candy, it's got something for everyone. As children, teenagers, and then adults we have to decide how much a big deal we want to make of it, and establish new rituals with our friends and families over the years as our collective balance of innocence, irony, and laziness fluctuate.  Witness poor Charles Boyle in "Brooklyn Nine-Nine" — the only Halloween enthusiast in a squad full of adult killjoys, stung more each year by his co-workers going out of their way not to get his costumes.

Rituals like Halloween present the most difficulty in a workplace. Even if there's some sort of office Halloween party, if you dress up you're just going to spend part of the day doing your same job, but in costume. The "Brooklyn Nine-Nine" creative team managed to find one for their fictional police precinct that became a yearly tradition and took the show to new heights: the Halloween Heist. What began as one episode rooted in character became a near-absurdist riff on the kind of needlessly elaborate thrillers that have double and triple-crosses stacked on top of one another until nothing makes remotely any sense anymore. Unfortunately going to elaborate, expensive lengths to steal from and deceive your co-workers isn't a ritual that we can apply in real life, but it made the Halloween episodes worth looking forward to. 

Even when seasons of the show aired at midseason, and thus nowhere close to Halloween, the writers found inventive ways to make sure each yearly Heist episode took place partially on October 31. So in honor of the holiday, here's every Halloween Heist episode of "Brooklyn Nine-Nine," ranked from worst to best.

By the seventh season, the Halloween Heists had become a genre unto themselves, and the writers had seemingly exhausted every possibility. What started as an extension of the brinksmanship between Jake and Captain Holt had grown to include the whole squad (usually with the exception of the useless Hitchcock and Scully) in multiple permutations. And since this was one of the years "Brooklyn Nine-Nine" didn't begin its season until January, an April episode began with multiple Easter bunnies fighting over a knockoff-brand Infinity Gauntlet. Weary background characters that we've never met before wonder aloud "Is this still going on?" as it's revealed that due to a series of mishaps, the Halloween Heist from the previous year is still happening six months later.

Unfortunately, having characters lampshade the idea that the heists are growing stale to the rest of the precinct isn't enough self-awareness to keep the episode itself from feeling stale, and "Halloveaster" is by far the weakest of the heist episodes. The structure, where first Cheddar the dog and then the equally guileless Scully accident eat the toy gems that everyone's attempting to steal, is half-clever as the characters have to wait until Valentine's Day and Easter to resume the heist. But the cleverness robs the story of its momentum — where every other heist episode has a winner that pays off the interplay between the characters, the revelation that Rosa was behind nearly every little thing the seventh time around seems arbitrary. Sure, it's typical Rosa and pretty badass when she jumps off the roof and reveals her name written in fire, but past winners had all had something to prove, and had deepened their relationships over the course of the heists. The only interesting bit that carries over to future episodes is Rosa's claim that by winning a three-part heist she's technically a three-time winner, and the debate that sets off within the squad.

The sixth season heist finds the "Brooklyn Nine-Nine" writers grasping at straws only slightly less than the following year. They also manage to call attention to it as Rosa outright says "Five heists was enough — literally nothing new can happen." And while the episode's focus on Terry is a welcome change of pace for an underserved character, the way the heist unfolds doesn't have much to do with Terry's story in any satisfying way. Often sitting either sitting out the heist or only participating reluctantly ("Heists are dumb!" is a direct quote), Terry has somehow come all the way around to "I love how crazy the heists get." He's also somehow masterminded an elaborate fake gas explosion on the previous Halloween, somehow anticipating that the heist would get delayed for seven months, long enough for him to manipulate Jake into suggesting they resume it on the day of his lieutenants' exam.

His "big speech" revealing how he fooled everyone else is as comedically delightful as any other heist episode, especially Mark Evan Jackson's delivery of "I was manipulated?" as even Captain Holt's husband Kevin is drawn into the fray this time around. But even though he's specifically betrayed by Jake three different times during the episode, Terry's motivation isn't to prove how the ruthlessness of the heists had gone too far, or how the squad had been unsupportive of his studying for the exam, or anything really. As cartoonish and detached from reality as the heists become, there's still a balance of character-based story beats that need to be at least hinted at to justify going so all-out crazy once a year. Some semblance of humanity has to tether us if we're expected to just roll with Rosa mailing Boyle to New Jersey in a box, or Scully having a twin brother we've never heard about before.

The fourth Halloween heist is one that marks the transition from relatively straightforward plots in the first three years — with fewer moving parts, at least — to more earth-shattering mic drop reveals with Gina's surprise mastermind of the events of the day. Granted, her point that competing for the title of "amazing detective-slash-genius" was excluding her as the lone civilian employee in the group is a fair one, but going to so much effort over the course of several months doesn't really fit with the Gina we've known for four years at this point. 

"Halloween IV" does introduce recurring heist character Bill, played by a perfectly cast Winston Story and an uncanny dead ringer for Joe Lo Truglio's Boyle, and the grimy details of Bill's life are an endless source of entertainment moving forward. The most effective subplot of the episode is the team-up of Rosa and Amy, as Rosa lets her guard down for one night in order to try and win the heist and embraces all of Amy's uber-organized, "Baby-Sitter's Club"-themed ways. But just like with Terry in Season 6, the revelation that Gina wasn't even hurt prevents any lesson from being learned about letting the heists get out of hand. It's also impossible not to wonder, as the heists grow more elaborate and involving, just how many crimes are going unnoticed in the 99th precinct with the staff so thoroughly pre-occupied.

The second heist, "Halloween II," is an important step in the heists becoming a category of episode unto themselves. Captain Holt's turn in the "big explanatory speech" role is brilliant, as he reveals he played Jake "like Frans Brüggen plays the flute." The revelation that he started planning for the heist the very moment the first one was over (fully nine months before Jake started working on his own plan) opened up the door for all the future heists to grow in scale and complexity. It's an important moment in the evolution of the character, as winning the second heist restores the power balance in the precinct (he is the Captain, after all), but reveals his deep competitiveness for what it is, and humanizes him in a way that signifies a real evolution from the robotic, cold version of the character we initially came to know.

And while Andy Samberg nails Jake's growing desperation as his plans go awry, if there's one knock against this episode it's that humiliating an arrogant Jake is pretty much par for the course for "Brooklyn Nine-Nine." He takes it in stride, rededicates himself to planning the following year's heist right away, and learns hardly anything other than a notch more respect for the captain he already respected. "Halloween II" also is bogged down a bit by a subplot involving Gina having trouble balancing taking classes with her dance troupe — while Chelsea Peretti's dancing is always welcome, storylines that require empathy for the hilariously caustic Gina can be a tough sell.

Season 5's "HalloVeen" wastes no time getting manic — Jake and Amy, now a couple for two seasons, reveal they went to bed fully dressed in preparation for "Heist Day," only to be startled by Captain Holt, who has seemingly been watching them sleep just to get psyched for the heist as well. We've left reality well behind at this point — Jake hyperbolically states at the briefing that planning for this year's heist is what got him through his stint in prison between seasons. Reflecting the new heist format of a free-for-all instead of teams ("Like 'Bachelor in Paradise'!" as Boyle puts it), what follows is pure heist chaos as everyone scrambles to steal the "Championship Cummerbund."

Boyle forms a team with Rosa and Terry (who incredibly agree to be called "The Tramps") and betrays his best friend, handcuffing Jake to a file cabinet. He escapes by signing up with returning Boyle doppelgänger Bill for a multi-level marketing scheme called Nutriboom, only to be one step behind Amy and Holt in the quest for the prize. Ultimately the reason Jake's desperation to win the heist seemed more pitched than usual, and the reason planning it got him through prison is revealed: he switches the cummerbund for one that says "Amy Santiago, Will You Marry Me?" and uses the heist to propose. It's a wholly unexpected, sentimental turn that instantly anchors the tradition in Jake and Amy's series-long story, and one of the most sentimental endings of any episode. As Holt petulantly points out, the proposal effectively means no one won the heist, but the goodwill is too much to really care about that technicality.

The first Halloween heist found "Brooklyn Nine-Nine" really beginning to hit its stride. Jake's bet with Captain Holt is a natural part of their early dynamic, as Jake bristled under Holt's ubiquitous professionalism, but for the first handful of episodes his attempts at rebellion usually end in his own embarrassment. And at first, his attempts to steal Holt's Medal of Valor seem disastrous — he falls through the ceiling, gets caught disguised as a janitor, tries to put doves in the air vents, and finally Amy tells Holt that Jake's been arrested scaling the building with a blow torch.

It's a welcome and surprising reveal, then, when it turns out Jake has elicited the help of the entire squad to steal the medal, and the majority of his fumbling was actually a misdirect. It's a testament to Andre Braugher's acting chops that Holt accepts defeat with grace and humility, and gamely calls Peralta "an amazing detective-slash-genius" as per the terms of the bet. You can tell Holt is actually perhaps proud that Peralta has learned how to work as a team inadvertently in his quest for personal glory. "Halloween" is also the only episode of "Brooklyn Nine-Nine" with a subplot devoted to the holiday itself, as Boyle teaches a cynical Santiago the true meaning of getting egged and surviving the costumed chaos amongst friends. The following years would conveniently forget the central premise that Halloween is one of the busiest, most chaotic days of the year for the squad, since they spend every subsequent Halloween episode hardly doing police work. But introducing the heists (and the running "title of your sex tape" gag) is enough to make this one of the best episodes of the show.

Entering its final season, "Brooklyn Nine-Nine" was faced with more challenges than just finding a satisfying way to bring its story to a conclusion — the nationwide protests against police brutality caused the creative team to scrap the original plan and first few episodes of the season, and introduce new plot elements to address to the tone of the country. Rosa quit the force to become a private investigator for victims of police misconduct, and Amy and Captain Holt eventually decided to leave the squad to join a new task force focusing on reform. It was a sober, somewhat successful attempt to blend the show's often wacky tone with the more complicated reality of police work. Fortunately, the reality of police work had been historically completely forgotten in the heist episodes, so a final heist was the perfect way to send off the series in "The Last Day."

A double-length episode with far too many twists and turns to sum up, "The Last Day" is a perfect finale full of familiar faces (Gina returns, of course) and callbacks to long-running gags. Once again, as Holt, Amy, and Jake (who's decided to leave the NYPD to raise his son) all conspire to turn the final heist into the "perfect goodbye," a series of mix-ups and confusing turns leads to the ultimate abrupt disappointment when Hitchcock, of all people, randomly buys the object of the heist from a now homeless Bill. It's a pitch-perfect result, as it completes a long evolution of the heists becoming more random and impossible to track, and it forces Jake to admit he was just hoping to avoid saying an emotional farewell.  

After some tears among the cast, they walk out of the 99 as a group for the last time.  And even though all of this was an impromptu, "non-holiday specific" heist, the episode ends by flashing forward to the following Halloween, when the gang surprises new Captain Terry with the final reveal: the heists will never stop, as long as the bonds between the squad remain.

The third and best heist episode captures the moment when a Halloween tradition is cemented between a group of loved ones. The squad is so committed at this point to making fun of Boyle's Halloween costumes that they all dress up in them briefly, to trick him into thinking they've finally caught the Halloween spirit themselves. But of course, the real spirit of Halloween on "Brooklyn Nine-Nine" is all about the heist, which functions as an alleged "tie breaker" between Captain Holt and Jake, who pick teams this time instead of bribing the squad to help them. Amy, suspect because of her status as Jake's "paramour" and Holt's teacher's pet, is left off both teams, to her frustration.

Melissa Fumero steals the episode as she plays Amy's growing anger, as both Jake and Holt assume her attempts to be sincere are attempts at subterfuge. It might be somewhat predictable that she ends up sabotaging them both and being crowned "Queen of the 99" herself, but it's the most satisfying reveal on a character level as both Jake and Holt have more than earned their comeuppance after three years of going full heist-brain. "Halloween III" is also when even the subplots of each episode start to get subsumed by the heist, as Gina assumes Boyle setting her up is part of the action. It's the most elaborate heist that's still actually easy to follow, and the best Halloween Heist on a show that created its own unique tradition.