Over the course of its five (and counting) seasons, Brooklyn 9–9 has never been anything less than consistently charming, rarely (if ever) turning out an episode that could be called ‘bad’. The show’s episode count is now well past 100, and almost every single one of those episodes sits somewhere in the range between “good” and “great.”
But there’s something about their Halloween episodes that are just a cut above even the already above average standards set by the show.
To set the stage: Waaaaaaay back in season one, immature-but-capable Detective Jake Peralta (Andy Samberg) was determined to prove his capability to his new captain, the unflappable Ray Holt (Andre Braugher). That determination took shape in a bet between the two on Halloween night, wherein Jake vowed to pull of a perfect heist and Holt was challenged to stop him.
Since then, every year has seen the duo engage in a new heist-centric bet, each time upping the stakes and involving the rest of the detective squad, including over-worked Sergeant Terry Jeffords (Terry Crews), Holt’s chaotic neutral assistant Gina Linetti (Chelsea Peretti), and detectives Charles Boyle (Joe Lo Truglio), Rosa Diaz (Stephanie Beatriz), and Amy Santiago (Melissa Fumero).
Each year, the characters (and writers) up not only the stakes of the competition but the number of elaborate and convoluted schemes utilized to steal that year’s prize. The result is five of the best episodes in the entire series, with even the weakest among them being laugh-out-loud funny and endlessly rewatchable (I know because I have rewatched them…endlessly).
So, without further ado, here is the complete and indisputable ranking of the Halloween Heists.
5. Halloween II
The Heist: Steal the watch off Captain Holt’s wrist.
The Competitors: Jake vs. Holt.
The Ultimate Detective/Genius: Captain Holt, in a flawless victory.
Best Gambit: Holt predicts (correctly) that just saying the word “bus” in front of Boyle will launch an outburst that Holt can record and re-purpose mid-heist.
About that ranking: Halloween II comes early enough in the show’s life that they still hadn’t quite figured out that the heist element was enough to sustain an entire half hour. The episode keeps interrupting the heist plot for a B-story about Terry getting frustrated with Gina’s lack of interest in her job, a story the show has told before and since (and done better, although I’m sure many in the audience have more patience for this iteration since it ends with Terry Crews cruising dancing around shirtless in a cape).
Even so, Halloween II suffers from being built around a twist that’s far too easy to spot. Having Jake pull off the heist within a couple minutes of the episode starting only to spend the rest of the night chasing after his ill-gotten goods is a neat enough reversal of the original template, but the whole thing is more labored and less inventive than these episodes, and Brooklyn 9–9 in general, promise.
But while the reveal that Holt is the evil puppet master behind Jake’s After Hours-ian plight, complete with near-sociopathic desire to defeat Jake, isn’t difficult to spot, Andre Braugher’s delivery of the Big Reveal monologue is an absolute hoot. Braugher makes a meal out of each and every line, and later episodes would pick up this competitive/childish/still-sorta-terrifying thread in his character established with this episode and find all kinds of new deranged avenues for it.
4. Halloween IV
The Heist: Steal a plaque from a padlocked caboodle placed in the middle of the precinct.
The Competitors: Jake and Gina vs. Holt and Charles vs. Amy and Rosa.
The Ultimate Detective/Genius: Gina. Or, should we say, the ultimate “person”/genius.
Best Gambit: Gina feigns an injury and then re-enters the precinct disguised in Amy’s pantsuits, which render her invisible.
About that ranking: If Halloween II is a weak set-up leading to a great punchline, Halloween IV is a terrific build to an only middling close. Gina outwitting the entire detective squad is fun, but Gina in general rolls through life like Bugs Bunny clowning on an entire planet of Elmer Fudds, so her victory doesn’t even have a good underdog kick.
Still, if the episode’s finale is somewhat limp, that doesn’t take away from how fun it is to get there. By season four, the creative team had fully embraced that the heist episodes 1) can be all about the heist, and B) take place in a heightened version of the show’s (already heightened) reality, which means schemes and counter-schemes unfold with the convoluted nonsensical precision of a Batman villain’s death-trap. Among other things, this episode features the introduction of Bill, the male prostitute Charles lookalike, Captain Holt going full-on berserker, and Rosa and Amy concocting an elaborate scheme based in part on (and with code names inspired by) the Baby-sitters’ Club.
That last one is an especial delight, as Rosa’s desire to win puts her on board with “all of your (Amy’s) nerdy crap.” Amy’s giddy reaction to this development is some of the most purely joyful work we’ve ever seen from Fumero on this show, so much so that when she declares that she never wants this night to end, we’re inclined to agree.
3. Halloween III
The Heist: Steal a crown from a locked interrogation room, and have possession of it at midnight.
The Competitors: Jake, and a team including Charles and Rosa, vs. Holt, with a team including Terry and Gina.
The Ultimate Detective/Genius: Amy, furious after an entire night being insulted and demeaned by Jake and Holt.
Best Gambit: Charles fills his pants with cockroaches. It’s not even especially clever, but…like…dude.
About that ranking: It’s a testament to just how good the top two picks are that this only comes in at three, as by any metric Halloween III is a terrific episode of Brooklyn 9–9 and a terrific episode overall.
III gets a lot of juice by centering around Amy Santiago, the show’s best character in this humble writer’s opinion, and by hanging all of this year’s hijinks onto Amy’s unsure place in the precinct as Jake’s new girlfriend and Holt’s devoted apprentice. Neither Holt nor Jake are sure that they can trust her, which might, on some other show, have resulted in a story where Amy had to prove her trustworthiness to one or both men. But this is Amy goddamn Santiago we’re talking about, goddammit, so instead she beats those two dopes at their own game, sends them on a wild goose chase, before tricking them into running up dozens of flights of stairs (with mid-climb puke breaks, of course).
The mayhem surrounding Amy’s triumph is top-notch as well, as the show no longer felt the need to prop up the heist with an unrelated B-story (there is a minor subplot involving Charles trying to fix Gina up on a date, but it’s short and fun and tied into the heisting going on), so the writers clearly took great glee in piling up as many fake-outs and surprises as they could into one 20-something minute go.
Also, if nothing else, between Stephanie Beatriz as Little Bo Peep and Terry Crews as Popeye, this episode’s costume-game was on point.
2. Halloween
The Heist: Steal Holt’s Medal of Valor from a locked safe in Holt’s office.
The Competitors: Jake vs. Holt.
The Ultimate Detective/Genius: Jake, thanks to a major assist from the squad.
About that ranking: It’s easy to forget this, but the original Halloween represented a pretty major sea-change in the dynamics of Brooklyn 9–9, giving an early signal that this show was capable of growth and change, unlike so many other sitcoms that cling to a single status quo for as long as possible.
See, every episode prior to Halloween followed a very similar trajectory: Holt would tell Jake to do something, or tell Jake specifically not to do something. Jake would do the opposite of what Holt said, immediately land into trouble, and then have to use the captain’s advice to clean up his mess, said mess usually stemming from Jake’s desire to be seen as a lone wolf badass, refusing to use any kind of help from his fellow detectives.
Halloween uses this immediately-familiar format as the springboard for its big twist: Jake actually learned his lesson from those previous times. He put aside his ego, worked with a team, and pulled off the impossible. While there will always be tensions between Jake and Holt (it’s kinda, you know, the engine of the show’s stories and comedy), Halloween was an early indicator that these characters could learn and evolve, something that has continued in all the following seasons.
As well as being a major stepping stone in the show’s growth, Halloween is just a terrific episode all around, with Jake’s frustrated attempts to outwit Holt taking on Coyote/Road Runner-like proportions of one-sided self-ownage. It set the gold standard for these episodes, and for a while it sure seemed like that magic would never be completely matched, let alone bested.
Bonus Point: Halloween features the first ever “Title of Your Sex Tape” joke, a running gag that’s only gotten funnier the longer that it’s run.
1. Halloween V
The Heist: Steal a champion cummerbund (“Or belt, as people call it,” Jake says) hanging from the ceiling in the middle of the precinct.
The Competitors: Everyone vs. Everyone Else.
The Ultimate Detective/Genius: Amy. Holt opines that the heist had no true winner, but come on, Amy had it last.
Best Gambit: I’m going to give it up for Amy somehow finding and training a decoy dog, identical to Holt’s own, to throw Holt off. She has allergies! That must have sucked for her!
About that ranking: Maybe it’s just recency bias, this being the last Halloween Heist episode to air to date. But I don’t know, man, I think this episode really is the peak for this tradition, a capstone so perfect that I’m honestly not sure if the writers wouldn’t be better off discontinuing the heist episodes and calling it quits here. It seems that impossible to top.
For starters, the every detective for themselves format this time out means that the episode is just stuffed to the gills with absurdly complex schemes and tricks. Elaborate pulley-systems, laser grids, Bill the male prostitute, and Jake somehow summoning an army of Handmaids, it just keeps piling up. By the time it turns out that Terry has been fed three different tracking devices (placed into his yogurt, because Terry loves yogurt) things have almost reached wacky overload.
And that’s when the episode pulls off its best, most surprising twist: All the frantic heisting has really all been a means for Jake to propose to Amy. The moment when Amy recovers the belt only to realize that Jake has altered it to read, “Amy Santiago, Will You Marry Me?” is a genuine jaw-dropper, made all the more perfect by just how well Fumero plays Amy’s stunned joy and Samberg plays Jake’s nervous excitement.
(Sidenote: Samberg’s really come into his own over the course of this show, right? If you had told me during season one that Andy Hot Rod Samberg would be a credible romantic leading man, I probably would’ve laughed you out of the room. But the Jake/Amy rivalry-courtship-relationship-engagement has been handled near-perfectly, and Samberg hasn’t missed a step in it.)
I mean, Jake’s proposal plan was contingent on his awareness that his girlfriend was smarter than him and she would of course be the last person holding the prize.
It’s silly, it’s sweet, it leaves you with a giant grin across your face, ready for more.
It’s Brooklyn 9–9.