The Funniest Episodes Of 'Brooklyn Nine-Nine' So Far

At its heart, Brooklyn Nine-Nine is a workplace comedy that plays fast and loose with the realities of police work, so it’s refreshing when an episode reminds us that the detectives of the 99th precinct are pretty good at their jobs. “Tactical Village” sees the squad attend operations training, where Amy runs into her ex Teddy (he loves pilsners!), which naturally sets off Jake’s jealousy and leads to him getting more than a little carried away in trying to beat his rival.

Elsewhere, “Tactical Village” does an excellent job of strengthening Diaz and Boyle’s friendship, as the former is genuinely hurt not to be invited to the latter’s wedding. Early episodes of Brooklyn Nine-Nine did a poor job of setting up a potential romantic relationship between the two, as Boyle’s inability to accept Diaz’s rejections came off as deeply problematic. Thankfully, this dynamic didn’t last long, and the show was all the better for it.

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As much as the officers of the 99th precinct goof off, at the end of the day, they still get results. The same can’t be said for detectives Norm Scully and Michael Hitchcock, who are so lazy and incompetent they’d have a hard time holding down any job, let alone one in law enforcement (which of course is part of the joke). “Hitchcock & Scully” finally lift the veil on these doofuses, revealing not only that the pair were good at their jobs in their younger years but were smoldering superstar detectives.

While this revelation is used primarily for comedic effect, the episode also takes the time to reinforce that even though present-day Hitchcock and Scully are (larger) shells of their younger selves, their hearts remain in the right place. Brooklyn Nine-Nine flashback episodes are always a good time — who doesn’t love seeing Captain Holt with a full head of hair? — but “Hitchcock & Scully” is the show’s finest 80s throwback to date.

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Alongside Craig Robinson’s Doug Judy, Jason Mantzoukas’s Adrian Pimento is arguably Brooklyn Nine-Nine’s best recurring guest character. In his self-titled debut, Pimento is introduced as a detective recovering from 12 years working undercover for mob boss Jimmy “The Butcher” Figgis. Pimento’s readjustment to society is painful, to say the least, as he’s suffering from his traumatic experiences working undercover. Brooklyn Nine-Nine takes a risky move here in going into such dark territory, but ultimately succeeds thanks to Mantzoukas’s broad, over-the-top performance.

Pimento would go on to figure heavily into season 3 and 4, striking up a passionate (and often uncomfortable) relationship with Diaz along the way. While some viewers may not be a fan of Jason Mantzoukas, he’s one actor we wish had become a series regular, as Brooklyn Nine-Nine just hasn’t been the same since he was last seen in season 4.

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It’s easy to forget now, but when “Jake & Amy” aired, it very well could have been the series finale (NBC had not yet rescued Brooklyn Nine-Nine from cancellation). We’re thankful this wasn’t the endpoint, but if it had been, “Jake & Amy” would have been an excellent place to leave off. In addition to the usual chaos you’d expect from a Brooklyn Nine-Nine season finale, “Jake & Amy” finds a way to end entirely with Jake and Amy exchanging wedding vows in front of their ragtag police family (Holt even officiates!).

Jake and Amy’s relationship has always worked because it leans into the fact that both characters are total doofuses (in their own way, of course) who support each other wholeheartedly. As such, it’s only fitting that their wedding works as a fakeout series finale, one which puts the series’ thesis statement into clear view: “Life is unpredictable. Not everything is in our control. But as long as we’re with the right people, we can handle anything.”

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Every good detective needs a nemesis. Of course, when you’re Jake Peralta, your nemesis also happens to be your best friend. Craig Robinson’s Doug Judy a.k.a. The Pontiac Bandit has made an appearance in every season of Brooklyn Nine-Nine, and his episodes are always a highlight. Doug Judy’s sophomore appearance in season two’s “The Pontiac Bandit Returns” is arguably the best of the bunch because it firmly establishes the crook’s rivalry with Peralta.

Still bitter about letting Judy getaway during their first encounter, Jake is reluctant to trust him in helping catch the “Giggle Pig” drug kingpin. While full of laughs, what puts “The Pontiac Bandit Returns” a step above is its conclusion, as Jake admirably sets aside his personal vendetta against Judy for the benefit of the squad, letting Judy go in favor of apprehending drug kingpin Tito Ruiz.

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Given Jake Peralta’s unhealthy John McClane obsession, It was only a matter of time before Brooklyn Nine-Nine did a Die Hard episode. Thankfully the show didn’t disappoint, as “Yippie Kayak” is a lovingly crafted homage to the classic police actioner (it even doubles as a Christmas episode!). The setup is pretty simple: when a group of thugs stages a hostage situation at a department store, Jake excitedly seizes the opportunity to carry out his own real-life Die Hard moment.

From there, “Yippie Kayak” cleverly pays homage to the 1988 classic in an amusing fashion, such as Dean Winters’ Vulture playing the incompetent operations leader and Gina being taken, hostage. It all culminates in an all-time gut-buster: Boyle saves the day but, in typical Boyle fashion, mistakenly utters the catchphrase “yippie ki-yay, motherf—ers” as yippie kayak, other buckets,” much to Jake’s dismay.

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“He Said She Said” is one of Brooklyn Nine-Nine’s more “serious” efforts. While these types of episodes may not be everyone’s cup of tea, they’re infrequent enough to maximize their impact, as Brooklyn Nine-Nine would be a very different show if it constantly navigated touchy subject matter. Then again, when an episode is as good as “He Said She Said,” maybe the show should take these kinds of risks more often.

Directed by Stephanie Beatriz, “He Said She Said” is an episode about and for the #MeToo era. Reflecting on her own experiences of sexism in the workplace, Amy fights to help a woman who claims one of her male co-workers sexually assaulted her. Humorous and topical, “He Said She Said” is an earnest attempt at examining gender power dynamics wrapped in the same good-natured storytelling that made Brooklyn Nine-Nine a hit in the first place.

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Up until the airing of “Moo Moo,” Terry Jeffords was generally characterized as the lovable, gentle giant of the Nine-Nine, a man who loves his family, his job, and his yogurt. That isn’t to say Terry didn’t get serious sometimes, but most of his stories involved worrying about his daughters and the antics of his other squad members. “Moo Moo” changed things. The episode takes a serious look at the issue of racial profiling in modern policing, as a white police officer nearly arrests an off-duty Terry.

Rightfully indignant, Terry decides to file a complaint against the officer but is met with resistance from Holt. This leads to one of Brooklyn Nine-Nine’s most heart-wrenching scenes; Holt explains to Terry how filing a complaint could hurt his career. Episodes like ‘Moo Moo” help reinforce how progressive Brooklyn Nine-Nine is. It’s hard to think of another comedy series that could successfully depict two black men (one of whom is gay) having a frank discussion about systemic corruption and racism.

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One of Brooklyn Nine-Nine’s more surprising accomplishments is that it made its annual Halloween episodes must-watch, appointment television. What started as a competitive bet between Jake and Captain Holt has turned into increasingly elaborate office heists involving the whole squad. Each Halloween episode has delivered something special, and while it’s tempting to go with the one that started it all, we have to give the nod to the much-anticipated follow-up.

“Halloween II” signaled that the show’s writers weren’t interested in simply doing a retread of the original heist. Instead, Holt orchestrates an intricate “revenge” plot against Jake to win, culminating in a shocking twist that sees Holt reveal his plan to Jake in supervillain fashion. Later Halloween episodes would deliver clever twists of their own, but none have rivaled the sheer audacity of Brooklyn Nine-Nine’s sophomore effort.

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Brooklyn Nine-Nine rarely breaks from its established formula, but when it does, it can deliver something extraordinary. As its title suggests, “The Box” is a stripped-down episode, providing a gripping single location story with just a handful of characters. Here, Jake and Holt interrogate a stoic, overly confident dentist (wonderfully played by guest star Sterling K. Brown) who’s committed a murder but seemingly covered his tracks at every turn.

The mystery alone is gripping and feels pulled from the best Agatha Christie serial, but what makes “The Box” the best episode of Brooklyn Nine-Nine is the way it holds a magnifying glass up to the master/protege relationship between Captain Holt and Jake Peralta.

In a lesser show’s hands, Jake probably never would have won his captain’s respect, even with the results he gets. Here, we see that even though they have seemingly contradictory views on law enforcement, both characters have found a way to learn something from the other. The fact “The Box” can tie such insightful character work into a truly stunning police procedural format merely is masterful.

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