Brooklyn Nine-Nine: The Funniest Episodes, Ranked

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Brooklyn Nine-Nine was created by Dan Goor and Michael Schur and had an eight-season run from 2013 to 2021. The show revolved around the NYPD’s 99th Precinct, led by the stoic, stern, and hilarious Captain Raymond Holt (Andre Braugher). The show’s primary focus is the squad, who rather ineptly but often successfully pursued criminals while dealing with hilariously absurd workplace drama. Occasionally, touching moments occur between characters as their arcs develop, but no moment of catharsis ever lasts very long because, without fault, something amusing always abruptly breaks the tension and keeps this workplace comedy grounded as lighthearted and boldly goofy.

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The cast includes Jake (Andy Samberg), the over-the-top goofball leading man; Amy (Melissa Fumero), the pencil-pushing goody two shoes; Rosa (Stephanie Beatriz), a monotone woman of few words with a comedic foreboding presence; Charles (Joe LoTruglio), the inept and desperate chatterbox always trying to win everyone’s approval (mostly Jake’s); Terry (Terry Crews), the stern muscle head lieutenant with a soft spot; and Gina (Chelsea Peretti), sarcastic, intelligent, witty, and never enthused about being at work.

What could have been a typical workplace comedy was elevated by this perfectly cast ensemble paired with excellent writing that let each character shine and develop in their own comedic way. The series will fondly be remembered, and as audiences sadly grieve the passing of star Andre Braugher, fans are revisiting one of the funniest television shows of all time. With all that said, here’s a ranking of the funniest episodes of Brooklyn Nine-Nine.

Update December 16, 2023: Following the tragic passing of star Andre Braugher, this article has been updated with more great episodes of Brooklyn Nine-Nine to make you laugh.

9 USPIS (Season 2, Episode 8)

While working with Rosa on a drug operation in the season two episode, “USPIS”, Jake is forced to team up with a post office inspector officer named Jack Danger, played by guest star Ed Helms. After learning that Danger pronounces his name “Donger”, Jake and Charles feel letdown, and things don’t get better when Danger and Jake start to disagree about how to handle the case. Danger’s incompetence gets in the way of Jake doing his job, which forces the NYPD officer to take matters into his own hands. Suffice to say, this doesn’t go too well.

What Makes It Hilarious

Sometimes, Brooklyn Nine-Nine is funniest when it leans into its immature sense of humor. “USPIS” isn’t the show’s smartest episode. After all, the episode’s main recurring joke revolves around the mispronunciation of a surname to make a penis gag. However, that doesn’t stop it from being laugh-out-loud hilarious. Helms steals the show as the character of Jack Danger, excellently portraying the character’s ineptitude and self-righteousness and, in doing so, acting as a great foil for Peralta.

8 The Box (Season 5, Episode 14)

If “USPIS” is Brooklyn Nine-Nine at its dumbest, season five’s “The Box” is the show at it’s most intelligent. An example of a bottle episode, it revolves around Jake and Holt spending the night interrogating the main suspect in a murder investigation, a dentist by the name of Phillip Davidson (Sterling K. Brown). Highly intelligent and chillingly calm, Davidson seemingly has an answer for everything, which makes things very difficult for the two officers. As the night goes on, and with a time limit on their hands, Jake and Holt find themselves resorting to some left-field tactics in order to get Davidson to confess.

What Makes It Hilarious

“The Box” is a smart, focused, and very well-written installment of the show. With a clear structure, lots of twists, and a magnificent guest performance by Brown – who went on to receive a Primetime Emmy Award nomination for his work here – it truly is Brooklyn Nine-Nine at its best. As well as being clever, though, it’s also very funny, with the episode’s unique structure and deliberate limitations providing fertile ground for some great comedy. The quick-witted dialogue between Peralta, Holt, and Davidson, and the bizarre ways Jake attempts to force a confession, make “The Box” a highly pleasing, fun, and rewarding watch that only gets better on second viewing.

Related: Brooklyn Nine-Nine Cast and Character Guide

7 The Fugitive (Season 4, Episodes 11 & 12)

The recurring character of Doug Judy (played by the very watchable Craig Robinson) popped up in every season of Brooklyn Nine-Nine, and the episodes he was in never failed to impress. The best of the lot, however, has to be the season four two-parter, “The Fugitive”. When a group of inmates escapes from a vehicle transporting them to prison, Jake turns to Doug to help him find them all. As is always the case with Doug Judy, though, he has his own motives, and Jake’s colleagues warn him of getting too close to someone who cannot be trusted.

What Makes It Hilarious

As is the case with all Doug Judy episodes, the reason “The Fugitive” works is largely down to the relationship between Jake and Doug. They make a strong pair, and their chemistry and banter is always fun to watch. This episode does a great job of expanding their relationship, pushing them further into friendship territory even if neither of them can trust the other. Both performers have so much charisma and report, and Robinson is easily one of the show’s best supporting characters. Overall, “The Fugitive” is a delightful and enjoyable pair of episodes that is amusing from beginning to end.

6 9 Days (Season 3, Episode 12)

One of the show’s more absurd episodes, “9 Days,” centers on Jake and Holt being quarantined in Holt’s house together after they are both exposed to mumps. As they both try and work on a case, they become sicker and sicker, and following the revelation that Jake only brought up the case to keep Holt occupied while his husband is away, Holt becomes angry, and the pair end up bickering.

Meanwhile, Terry has to deal with Hitchcock and Scully when both of them refuse to work after Terry took their sandwich.

What Makes It Hilarious

Like others on this list, the reason “9 Days” succeeds is very much down to the pairing of Peralta and Holt and the performances of Samberg and Braugher. From their early fighting to their delirious ravings, both are hilarious, and it’s a real treat to see the usually strict Captain Holt become so wildly unhinged. Brooklyn Nine-Nine regularly skirted around absurdity but rarely did it fully embrace it. That’s not the case with “9 Days”, though, which fully embraces its wacky plot and is all the funnier for it.

5 The Suicide Squad (Season 6, Episode 18)

“The Suicide Squad” acts as the season six finale and revolves around the 99 making allies with old foes in order to save their jobs. In order to take down the corrupt Commissioner Kelly, the gang puts together a suicide squad of their worst enemies in the NYPD, which consists of Holt’s arch-nemesis Chief Wuntch (Kyra Sedgwick), the incompetent Captain CJ (Ken Marino), and Major Crimes member Keith, also known as the Vulture (Dean Winters). With the team in place, Jake formulates a plan that involves staging a fake kidnapping. However, in true Brooklyn Nine-Nine style, things don’t quite go to plan – not at first, anyway.

What Makes It Hilarious

Filled with twists, turns, and betrayals that keep the audience guessing the entire time, “The Suicide Squad” is a clever and highly engaging installment of the show that serves as a truly epic season finale. Nevertheless, its boldness and high stakes never take away from the show’s humor, which is at some of its best in this episode. Having the Nine-Nine team up with their worst enemies was a genius idea and led to some hilarious clashes of personalities and more than a few great gags.

4 Coral Palms: Part I (Season 4, Episode 1)

“Coral Palms”, the three-part story that opened season four, sees a shake-up to the format by focusing solely on Jake and Holt, who are in witness protection in Coral Palms, Florida, following the events seen at the end of the last season. Under strict instructions not to carry out any police work, they must make new lives for themselves in the community, which includes taking on fake names. While Holt is happy to obey orders, Jack quickly becomes bored with normal life and is keen to investigate the case that put them there in the first place. This causes tension between the two men and, when Jake gets promoted at the kids indoor play area they both work at, he makes Holt take on duties that he doesn’t want to do as a form of revenge, such as dancing at a child’s birthday party.

What Makes It Hilarious

“Coral Palms: Part 1” is refreshing in how it allows viewers to see both characters in a different light, which also leads to a lot of laughs. The contrast between Jake and Holt – with Jake being immature and clownish and Holt being serious and stern – was always the show’s backbone, providing a wealth of both comedic and dramatic material. In this episode, with no other main characters appearing for the entirety of the runtime, that conflict is put front and center in a way that it never had been before. With a tension between the two characters that builds and builds throughout and only gets funnier as it does, this first part of a great three-part story is both suspenseful and silly in all the right ways.

3 The Party (Season 1, Episode 16)

A relatively early episode in the show’s run, “The Party” sees the squad being invited to a fancy party at Holt’s house, which he shares with his equally pompous husband, Kevin. Realizing that the gang are not accustomed to the kind of mature and highbrow party Kevin is no doubt planning to throw, Terry takes it upon himself to make sure everyone knows how to act appropriately, or, as he puts it, they need instructions on “interacting with grownups”. This includes giving them a wardrobe run down (no shorts) and stressing the importance of punctuality (and bringing wine). Of course, everyone blows it from the start, with Jake arriving late, Scully wearing shorts, and everyone bringing the same bottle of cheap wine as a gift. Ultimately, their strange behavior gets them all kicked out of the party.

What Makes It Hilarious

“The Party” is a rare example of an episode that puts all the main characters in the same place at the same time, as opposed to dividing them into smaller groups for three distinct subplots. In doing so, the viewer gets to see how each character acts in the same situation – a fancy party – which allows all of them to shine. From Gina receiving attention from a group of psychiatrists who are fascinated by her quirks, to Jake pretending to have read an article in The New Yorker in order to impress Kevin, to Amy’s cringe-inducing attempts to win Holt over, each character gets to be funny in their own unique ways, which is highly entertaining to watch.

Related: Brooklyn Nine-Nine: Where the Cast is Today

2 The Last Day Parts 1 and 2 (Season 8, Episodes 9 & 10)

Right up until the end, Brooklyn Nine-Nine was still delivering the laughs, with the epic two-part conclusion, “The Last Day” going down in TV history as a truly perfect series finale. The episodes center around one final heist before Holt and Amy leave the precinct for their new police jobs. Jake, however, is also planning to leave to raise his and Amy’s son and wants to use the heist as a perfect way of saying goodbye. Having planned it far in advance, Jake intends it to be the big reveal of his own last day, where he plans to announce at midnight that he will also be leaving. Everyone goes all-out, which leads to some hilarious moments, including Holt revealing a tattoo and Amy handcuffing Jake to a fake hospital bed.

What Makes It Hilarious

Like all great TV finales, “The Last Day” is an emotional rollercoaster filled with touching moments and sentimental callbacks. Despite this, the two-part story never skimps on the comedy and delivers just as many, if not more, laughs than any normal episode of the show. A joyous last hurrah, it manages to cram everything that is good about Brooklyn Nine-Nine into just over 45 minutes. With a multitude of fun cameos, including Gina’s hilarious and typically exaggerated return, and a main cast on fine form, “The Last Day” is both a riotous slice of sitcom television and a fitting ending for a much-loved show.

1 HalloVeen (Season 5, Episode 4)

One episode every season, Brooklyn Nine-Nine celebrated the spooky season with a Halloween Heist episode, which never failed to be big on laughs. Without a doubt, the best of the bunch was season five’s “HalloVeen” which sees Jake, Holt, and Amy team up against Terry, Rosa, and Charles to compete for a champion cummerbund (or “belt”). The most intricate and elaborate heist at this point in the show, some of the gang’s many madcap plans include Jake using someone as a Gina stand-in, and Holt training his dog, Cheddar, to steal the belt. It all ends when Amy successfully gets her hands on the belt, only to find Jake has used it as a way of proposing to her.

What Makes It Hilarious

Over the top, epic, silly, yet ultimately sweet, “HalloVeen” is everything a Halloween sitcom episode should be. By season five, the concept could easily have become stale, but this episode imbues the idea with a new energy and new lease of life, that makes it highly entertaining to watch. The appeal of these episodes has always been watching the characters we love trying to one-up one another, all the while becoming more competitive and single-minded as the episode progresses. “HalloVeen” pushes that to new and hilarious levels, before pulling the rug from underneath the viewer, and delivering one of the best climaxes in the show’s history. Few shows manage to pull off laugh-out-loud hilarity and touching sentimentality in equal measure, which only highlights how good a show Brooklyn Nine-Nine really is.

Stream Brooklyn Nine-Nine on Peacock

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