The 15 Best Episodes of Brooklyn Nine-Nine Of All Time

NBC’s first season of Brooklyn Nine-Nine has continued to produce the same comedic high-energy episodes fans of the series were used to seeing, allaying fears that quality would change after Brooklyn was saved from cancellation. The Nine-Nine squad is as hilarious as ever, while still managing to touch on some real-world issues as they explore the “toit” relationships behind the award-winning ensemble cast.

Today we are going to take a look at ten of the best episodes Brooklyn Nine-Nine has aired over the last six seasons, though it’s hard to find a truly bad episode of the series. The following episodes showcase not only the funniest comedic elements of the series but also key moments for specific characters that might tug on a few heart-strings.

Updated April 28th, 2020 by Alyssa Avina. Brooklyn Nine-Nine has just wrapped up their 7th season with another fantastic finale, and we can’t help but take a look back at some of the greatest episodes of the series of all-time. There are many to choose from, but these are the ones that left us laughing, crying, and awestruck all at once. The Nine-Nine has a way of doing that to you, and it makes it hard to choose favorites because of it, but these are the best of the best, trust us.

15 Season 2, Episode 3: “The Jimmy Jab Games”

Towards the beginning of season 2, we saw the ultimate team-building exercise from the Nine-Nine with the “Jimmy Jab Games”. It was a competitive yet comical set of games that tested each member of the squad’s skillsets.

Not only was the episode filled with hilariously disastrous moments, but it was the episode where Jake realized and admitted to Rosa that he still had feelings for Amy. He even let her win the games because of his feelings for her. It was adorable, really.

14 Season 7, Episode 3: “Pimemento”

Adrian Pimento is hands down the funniest side-character in Brooklyn Nine-Nine history. He is also a little bit crazy and always has trouble following him everywhere he goes. In this episode, Pimento comes to Jake and Charles claiming someone is trying to kill him.

The only problem is he can’t remember who and he now seems to have short-term memory loss…much like Leonard in the classic film Memento did. Jake repeatedly tries to reference the movie to Adrian and Charles and neither of them has seen it. Instead, they think it’s just like the movie Finding Dory. Needless to say, it was a fan-favorite episode of the season.

13 Season 5, Episode 4: “HalloVeen”

We always love the Halloween Heist episodes of Brooklyn Nine-Nine and part of why is because they seem to up the ante every single year. We are always on the edge of our seats because of this, waiting to see who is going to be crowned the “Ultimate Detective/Genius”, but this heist episode was different.

No one technically won, but Jake did finally propose to Amy in the most beautiful and quintessentially “Jake and Amy” way possible. Aside from the proposal being heart-warming, the heist’s events unfolding before that was a sight to behold, too.

12 Season 4, Episode 18: “Cop-Con”

In this season 4 episode, the squad is going to Rochester to a Cop-Con which is basically a huge convention for cops to see the latest gear and techniques in their field. But the Nine-Nine uses it as an excuse to party.

When their original plans are thwarted, they decide to throw a party of their own in their rooms while trying to evade Holt’s judgment and scolding. They end up getting so inebriated they can’t remember what happened the night before and must try to crack the case before Holt’s presentation is ruined.

11 Season 4, Episode 16: “Moo Moo”

Brooklyn Nine-Nine has a wonderful way of touching on important issues without being controversial or demeaning. A perfect example of this is “Moo Moo”, an episode that focuses on Terry being stopped by another cop in his own neighborhood because he’s a black man.

It wasn’t until the cop realized Terry was, in fact, a cop himself, that the issue was dropped. But for Terry, it still was a major problem that needed to be reported. The way the writers tackled this very real issue that happens all of the time was respectful and rather poignant.

10 SEASON 2, EPISODE 23: “JOHNNY AND DORA”

Following a number of hurdles that included an undercover operation and ill-timed relationships, Detectives Jake Peralta (Andy Samberg) and Amy Santiago (Melissa Fumero) were both finally single when Santiago declared no more relationships with cops just as Jake was about to make his move.

They would then awkwardly go undercover as newly engaged couple “Johnny and Dora,” resulting in a couple of fake make-out sessions before Jake and May’s first official kiss. This episode also featured an incredibly emotional moment from Detective Raymond Holt (Andre Braugher) who was forced to leave the Nine-Nine by his recurring nemesis Madeline Wuntch (Kyra Sedgewick) in order to save his squad from being split up.

9 SEASON 3, EPISODE 10: “YIPPIE KAYAK”

One of the more endearing qualities of Peralta is his obsessive love for Die Hard which has shaped his personal and professional life and has resulted in a number of hilarious episode gags and even a guest appearance from Reginald VelJohnson. The third season even saw Peralta, Detective Charles Boyle (Joe Lo Truglio) and Gina Linetti (Chelsea Peretti) trapped in a department store hostage situation on Christmas, poised to re-enact Jake’s favorite film.

Of course, things don’t quite go as Jake would hope when the German terrorists turn out to be French Canadian robbers and Peralta is forced to sit on the sidelines while Boyle butchers John McClane’s iconic line, saving the day with a dramatic rescue from the air vents. This episode also featured the always comedic Keith “The Vulture” Pembroke (Dean Winters) as acting Captain of the 99, in one of many fan-favorite recurring roles from the Vulture.

8 SEASON 1, EPISODE 12: “THE PONTIAC BANDIT”

It’s difficult to pick the best of guest star Craig Robinson’s annual Doug Judy appearances, as watching his and Jake Peralta’s friendship develop has arguably been just as rewarding as Jake and Amy’s “romantic-styles” relationship. Robinson’s first appearance came as the titular Pontiac Bandit, a car thief Peralta had been investigating for years.

Judy’s first interaction with Peralta is a lie, as he is caught on identity thief charges but instead offers up Peralta’s nemesis, the Pontiac Bandit. This kicked off a series of bait-and-switch games played by Judy with each season’s appearance that would bring the two closer while also dragging Judy closer to the right side of the law.

7 SEASON 5, EPISODE 22: “JAKE AND AMY”

The fifth season of Brooklyn was building towards two huge moments for the Nine-Nine, Jake and Amy’s wedding and Holt’s campaign to achieve his lifelong goal of becoming the Commissioner of the NYPD. In “Jake and Amy,” Holt is set to learn the results of the election while the wedding is ruined by a bomb set by a criminal from Amy’s past (Kyle Gass of Tenacious D).

While the season-long planning of the wedding was ruined by the bomb, Boyle set up a perfect replacement wedding at the precinct officiated by Holt. The episode ended on the biggest cliffhanger yet with the postponement of Holt’s commissioner reveal, especially considering the series was canceled by Fox shortly after the episode.

6 SEASON 5, EPISODE 10: “GAME NIGHT”

Inspired by actress Stephanie Beatriz’ own coming out as bisexual, “Game Night” featured her character Rosa Diaz doing the same during a morning briefing to the squad. Determined but scared to tell her parents (guest stars Danny Trejo and Olga Merediz), Diaz asks Peralta for help through an awkward dinner and even worse family game night, which leaves the Diaz family at odds with each other.

The episode featured a touching scene from Beatriz and Trejo as the father accepts his daughter, and also showcased Jake and Diaz’ friendship and Peralta’s continuing growth into a mature and responsible adult. Brooklyn Nine-Nine went on to win the GLAAD Media Award for Outstanding Comedy Series in 2018.

5 SEASON 1, EPISODE 13: “THE BET”

This episode serves as the culmination of a season-long bet over who is the better detective, Peralta or Santiago. The wagers? Jake’s prized 1965 Ford Mustang versus Amy having to go on the worst date ever in Jake’s Mustang.

When Santiago loses at the last minute, she is forced out on the meticulously planned worst date which turns into a stakeout on a rooftop where the two end up actually having a good time. The episode served as one of the first moments that teased the eventual romance between Jake and Amy, though it would still be a couple of seasons until those feelings were fully realized.

4 SEASON 4, EPISODE 15: “THE LAST RIDE”

Upon news that the Nine-Nine is about to be shut down, Peralta and Boyle decide to go out in a blaze of glory against mean drug dealers, while Santiago and Holt rush through a planned nine-year mentorship in ten hours, and Sergeant Jeffords (Terry Crews) with Diaz battles against Hitchcock (Dirk Blocker) and Scully (Joel McKinnon Miller) for the precinct arrest record.

In true Nine-Nine fashion, the precinct is saved by Gina’s live-streams that not only captured numerous moments of hilarious cement drinking pranks, but also an impassioned speech by Holt when Peralta and Boyle decide to go for the bigger bust instead of saving the precinct. The episode features great moments from the entire squad and perfectly exemplifies the depths the show can reach.

3 SEASON 5, EPISODE 20: “SHOW ME GOING”

Another episode that proves the show isn’t all about comedy is the fifth season’s “Show Me Going,” which features the squad dealing with the news that Diaz is involved in an active shooter situation that has already suffered police casualties. It’s a tense environment in the precinct and Holt struggles to comfort his squad, hoping to rely on Peralta for the Nine-Nine’s emotional support.

Jake goes against his own instincts to defy orders and try to help Diaz, and instead does the right thing and chooses to be there for the Nine-Nine until Diaz’ safe return. It was an emotional episode that highlighted the deep relationships this team has developed with one of the least emotional members of the team.

2 SEASON 2, EPISODE 4: “HALLOWEEN II”

Brooklyn Nine-Nine is known for every season’s recurring themed-episodes, such as the annual appearance of Robinson’s Doug Judy or the heist-based Halloween episodes. While it’s again hard to pick the best Halloween episode, season two’s “Halloween II” comes out as the best due to the creation of the ongoing challenge between detectives and their captain.

While Peralta prompted the events of the first and second Halloween heists, the episode reveals that Holt had engineered the events of the second heist through detailed manipulations and planning begun one year prior. Holt’s pitch-perfect delivery of his plans like a classic Bond villain clinches this Halloween as the best of the bunch.

1 SEASON 5, EPISODE 14: “THE BOX”

“The Box” features Holt and Peralta locked in an intense interrogation against arguably one of the Best guest-stars to hit the Nine-Nine, Sterling K. Brown. While we’ve seen police interrogations before, none can compare to the mind games witnesses in this episode.

Brown’s cool and collected Dr. Philip Davidson used his arrogant intelligence and turned Holt and Peralta’s interrogation techniques back on them. This calls in to question Holt’s trust in Peralta’s competence. At the end of the day, Peralta is able to attack Davidson’s pride and get a nail-biting confession that showcased why Peralta is the star of Holt’s detective squad.

About The Author

Scoot Allan
(193 Articles Published)

Entertainment reporter, writer, and all-around geek, Scoot Allan has written for print and online media sources like Geek Magazine, GeekExchange, GrizzlyBomb, WhatCulture, RoguePlanet.tv and the Urban 30 before joining CBR, ScreenRant, GameRant and The Gamer as a staff writer. He enjoys salad but prefers french fries.

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