Ranked: Every Brooklyn Nine-Nine Halloween Heist Episode

Halloween is a ritualistic holiday. We have to decide how big of a deal we want to make of it as children, teenagers, and adults. And establish new rituals with our friends and families as our collective balance of innocence, irony, and laziness fluctuates over time. In “Brooklyn Nine-Nine,” Charles Boyle, the only Halloween enthusiast in a squad of adult killjoys. Is stung more and more each year by his coworkers who go out of their way not to get his costumes.

Even when seasons of the show aired in the middle of the year. Far from Halloween, the writers devised ingenious ways to ensure that each yearly. Heist episode took place in part on October 31. So, in honour of the holiday, here’s a list of every “Brooklyn Nine-Nine” Halloween Heist episode, ranked from worst to best.

Valloweaster (Season 7, Episode 11)

The writers had seemingly exhausted all possibilities. What had begun as an extension of Jake and Captain Holt’s brinkmanship had expanded to include the entire squad (usually with the exception of the useless Hitchcock and Scully) in various permutations. Because “Brooklyn Nine-Nine” didn’t premiere until January this year, an April episode featured multiple Easter bunnies fighting over a knockoff-brand Infinity Gauntlet. As it’s revealed that the previous year’s Halloween Heist is still going on six months later due to a series of mishaps, weary background characters we’ve never met wonder aloud, “Is this still going on?”

Unfortunately, having characters tease the rest of the precinct about how the heists are getting stale isn’t enough self-awareness to keep the episode from feeling stale, and “Halloveaster” is the weakest of the heist episodes. The structure is half-clever, as the characters have to wait until Valentine’s Day and Easter to resume the heist after Cheddar the dog and the equally guileless Scully accidentally eat the toy gems that everyone is attempting to steal.

Cinco De Mayo (Season 6, Episode 16)

Terry has somehow worked his way around to “I love how crazy the heists get” after either sitting out or only reluctantly participating (“Heists are dumb!” is a direct quote). He also orchestrated an elaborate fake gas explosion the previous Halloween, somehow anticipating that the heist would be postponed for seven months, long enough for him to persuade Jake to suggest that they resume it on the day.

Halloween IV (Season 4, Episode 5)

The fourth Halloween heist marks a shift from the relatively simple plots of the first three years — with fewer moving parts, at the very least — to more earth-shattering mic drop reveals with Gina’s surprise mastermind of the day’s events. But putting in so much effort over several months doesn’t seem to fit with the Gina we’ve known for four years.

Halloween II (Season 2, Episode 4)

The second heist, “Halloween II,” is a significant step toward heists becoming their own category of episode. Captain Holt’s performance as Jake in the “big explanatory speech” role is outstanding, as he reveals that he played Jake “like Frans Brüggen plays the flute.”

HalloVeen (Season 5, Episode 4)

 He gets away by joining a multi-level marketing scheme called Nutriboom with returning Boyle doppelgänger Bill, only to fall behind Amy and Holt in their pursuit of the prize. Jake’s desperation to pull off the heist was. In the end, the reason for his unusually high pitch.

Halloween (Season 1, Episode 6)

“Brooklyn Nine-Nine” was really getting into its stride after the first Halloween heist. As Jake resented Holt’s omnipresence. But his attempts at rebellion usually end in his own embarrassment for the first handful of episodes. And his attempts to steal Holt’s Medal of Valor appear to be a failure at first.

When it turns out that Jake has enlisted the help of the entire squad to steal the medal. And that the majority of his fumbling was actually a misdirect. It’s a welcome and surprising revelation. It’s a testament to Andre Braugher’s acting prowess that Holt accepts defeat with grace and humility. One of the show’s best episodes.

Halloween III (Season 3, Episode 5)

They’ve finally caught the Halloween bug. But, of course, the true spirit of Halloween on “Brooklyn Nine-Nine” is all about the heist. Which serves as an alleged “tie breaker” between Captain Holt and Jake. Who this time choose teams rather than bribing the squad to assist them. Amy is left off both teams, much to her chagrin. Due to her status as Jake’s “paramour” and Holt’s teacher’s pet.


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