Ranking the ‘Brooklyn Nine-Nine’ Halloween Heists Ahead of the Final Season (POLL)

Brooklyn Nine-Nine Season 7 Valloweaster
Jordin Althaus/NBC

With the final season of Brooklyn Nine-Nine steadily approaching (Thursday, August 12 at 8/7c on NBC), when better to take a look back at what has become an annual event, the Halloween heist?

The tradition began with Detective Jake Peralta (Andy Samberg) insisting he’d make a good criminal and no one could catch him — and setting out to prove it by stealing Captain Raymond Holt’s (Andre Braugher) Medal of Valor. Over the years, it’s evolved to include the entire squad competing against one another and extended to other holidays (Cinco de Mayo, Valentine’s Day, Easter). But what’s remained the same is that these heists bring out the absolute worst in everyone, including but not limited to insults, tasers for gifts, and chloroforming and shipping a friend to New Jersey.

Below, we’ve ranked the heists over the years from least to most entertaining and memorable.

“Cinco de Mayo” (Season 6, Episode 16)

With then-Sergeant Terry Jeffords (Terry Crews) seemingly stressed out about his upcoming lieutenant’s exam, the squad decides to distract him with a heist. Working in pairs, they had to steal Scully’s (Joel McKinnon Miller) medical alert bracelet. Everyone betrayed their partners, of course. In the end, Terry won, having orchestrated everything (including the circumstances preventing them from heisting on Halloween). The highlights are easily Scully being revealed to be a twin and Holt’s husband Kevin (Marc Evan Jackson) getting in on the heisting a bit (because he didn’t want that bracelet hanging in their house). But overall, it just wasn’t as fun as the others. (And Jake was right when, at one point, he admits, “this is officially getting too hard to track.”)

“Halloween IV” (Season 4, Episode 5)

With previous winners Holt, Jake, and then-Detective Amy Santiago (Melissa Fumero) competing to determine the “champion of champions,” they play for a plaque reading “The Ultimate Detective/Genius.” Gina (Chelsea Peretti) fools everyone by seemingly sending herself to the dentist (though she later reveals she lost her front teeth a long time ago) before emerging as the victor, calling the use of “detective” on the plaque discriminatory. The path to getting there just isn’t as entertaining as the other heists’, though we do like the fact that Gina plants copies of the plaque to make everyone think they won — and she’s able to sneak back in and be “invisible” by wearing Amy’s clothes.

“Halloween III” (Season 3, Episode 5)

In the third heist, Jake and Holt compete against one another to steal a crown. They choose the others to be on their teams — except Amy. Neither trusts her not to work for the other; she and Jake are dating and she’d do anything to win Holt’s approval. We very much enjoy Amy getting back at them by stealing the crown herself (and making them walk up over 30 flights of stairs in the process). But Boyle (Joe Lo Truglio) putting roaches in his pants as part of Jake’s plan is completely unnecessary.

“Halloween” (Season 1, Episode 6)

It’s the one that started it all. After seemingly losing and getting caught multiple times along the way, Jake ends up cuffed in an interrogation room. That’s when he reveals to Holt how he’s actually pulled it off — with the help of the rest of the squad along the way. It’s actually the simplest one, and there’s just something special about everyone working together to get the job done before the heists get more and more complicated each year.

“Valloweaster” (Season 7, Episode 11)

Once again working in pairs but handcuffed to their partners, the squad’s goal is to steal the gems of a knock-off of the Avengers‘ Infinity Gauntlet. When Holt’s dog Cheddar swallows them, the heist is postponed to Valentine’s Day. When Scully then swallows the gems, taking that victory away from his partner Detective Rosa Diaz (Stephanie Beatriz), it’s once again postponed, to Easter — at which point, everyone dresses up as bunnies. Rosa shocks everyone, not only by finding a way around staying cuffed to her partner (now a filing cabinet) but by becoming a three-time winner. Yes, she orchestrated everything, including the multiple postponements, tricking Cheddar and Scully into swallowing the gems, and getting rid of her first partner (though she doesn’t have to pay a doctor to declare him unfit to complete, given his health).

“Halloween II” (Season 2, Episode 4)

For Round 2 of the Halloween bet, Jake decides he’ll steal the watch off Holt’s wrist and goes so far as to enlist the help of a pickpocketer. The productions become more elaborate, only for Holt to turn the tables on Jake from the first heist in an interrogation room. He has the entire squad help him win. The highlights: the reveals that Holt used a recording of Boyle from eight months earlier and that the captain’s the costumed partygoer who steals Jake’s badge. And so begins the very early planning for the following year’s heist.

“HalloVeen” (Season 5, Episode 4)

Holt may not have been a fan (as he says the following year), but this one holds a special place in our hearts — in large part due to the fact that Jake uses the heist to propose to Amy, switching out the cummerbund with one that reads “Amy Santiago, Will You Marry Me?” But that’s not the only reason this one tops our list. The cold open is also so much fun, as Amy, Jake, and Holt, in the couple’s bedroom, one-up each other in heist prep. There’s Amy’s repeatedly declaring that Jake can’t surprise her (until he does). There’s the fake Cheddar (and Holt’s reaction to him). There’s the Handmaid’s Tale takeover in the squad room.

Now it’s your turn. Which heist is your favorite? Vote in our poll below.

Brooklyn Nine-Nine, Eighth and Final Season Premiere, Thursday, August 12, 8/7c, NBC