The 20 Best Episodes of Brooklyn Nine-Nine Of All Time

Summary The best Brooklyn 99 episodes shine thanks to the amazing ensemble of talented actors at the 99th Precinct.

The show blends comedy with serious subject matter, creating a unique and compelling viewing experience.

Brooklyn Nine-Nine's episodes are acclaimed, with standout moments like Jake's Backstreet Boys lineup and Rosa's coming out.

Brooklyn Nine-Nine was remarkably consistent during its run and the best Brooklyn 99 episodes matched up with any other comedy on television. Brooklyn Nine-Nine premiered in 2013 on Fox, and while it gained a lot of fans and critical praise for its off-the-wall humor, Fox canceled it after five seasons. Luckily for fans, NBC saved the show and aired it for three more seasons, and presented some more of the best Brooklyn 99 episodes, without ever missing a beat. By the end, the series ended with eight seasons and 153 episodes, while also picking up a Golden Globe along the way.

The best Brooklyn 99 episodes focused on the amazing actors that made up the cops at the fictional 99th Precinct of the NYPD in Brooklyn. No matter how the immensely talented cast was paired up in any given episode, it typically made for hilarious and compelling television. Every season of the series was critically acclaimed, with four seasons sitting at 100% on Rotten Tomatoes, and that makes finding the best Brooklyn 99 episodes hard to narrow down. It was often at its best when it blended comedy with serious subject matter in a way few shows could.

Related 25 Lighthearted Shows Like Brooklyn Nine-Nine As wonderful as Brooklyn Nine-Nine is, no show lasts forever, so it's important for fans of cop comedies to have a backup series to turn to.

20 "Pilot"

Season 1, Episode 1

Close

It's impossible to look at the best Brooklyn 99 episodes without considering where it started. The pilot episode set up the show for what fans could come to expect over the years. It has a lot of work to do in setting up the tricky tone of a funny cop show as well as introducing the large ensemble.

However, it is leaning into the dynamic between Jake Peralta and Captain Raymond Holt that shows the sitcom's promise. While it took a while to find its footing, the pilot episode of Brooklyn Nine-Nine still showed the humor that defined the comedy series.

The first episode introduced the characters that would carry the show, with Jake and Amy as the first two to hit the screen. However, it did things a little differently, with the theme music coming at the end. "Pilot" was surpassed many times over, but it's incredibly important for the series overall.

19 "99"

Season 5, Episode 9

In season 5, the ninth episode kept the irony intact, as it was the 99th episode and was titled "99." What was funny about this episode was that it was set up like a Brooklyn Nine-Nine series finale, even though the show still had a ways to go.

The episode centers around the funeral of the precinct's former captain in Los Angeles only for Holt to learn he is being considered as the next commissioner and has to make it back to New York. This was also a rare episode where the cast didn't split up to deal with different cases, and they were mostly together for the entire installment.

It was also different in that it didn't take place at the police department and instead showed them in a more natural environment. The show proved why it was so funny, by putting these characters into ridiculous situations, such as trying to sleep during a "cow orgy."

18 "DFW"

Season 5, Episode 17

"DFW" was the fifth episode of season 5 and the first time Jake's sister Kate (Nasim Pedrad) was introduced. Finding her presence annoying and terrified by the prospect of her moving to New York for good, Jake and Amy attempt to do whatever it takes to convince her to leave.

This storyline is funny enough and there are some funny subplots with Terry doing yoga with Charles and Gina setting Rosa up on a date. However, the real reason this ranks among the show's best episodes is because it features Brooklyn Nine-Nine's best cold open.

This all started with one of the best gags in the show's history as Jake was trying to help a woman pick out the man who killed her brother from a lineup. The woman only remembers that the killer sang a Backstreet Boys song at a bar that day, so Jake starts to sing "I Want It That Way," with everyone in the lineup singing along with him. It is the best example of the show embracing its absurd humor.

17 "Operation: Broken Feather"

Season 1, Episode 15

Close

The season 1 episode "Operation: Broken Feather" had one of the show's many guest star appearances and one of its biggest. The episode also develops the relationship between Jaek and Amy more with them teaming on a hotel robbery case. However, when Jake finds out Amy is considering moving to Major Crimes, he is conflicted.

This was the episode where Brooklyn 99 gained most of its fans since it aired after the Super Bowl in 2014. Adding someone like Adam Sandler to the Brooklyn Nine-Nine guest cast got people paying attention. The writers turned in one of the best Brooklyn 99 episodes, which helped the show keep many of those fans. The jokes were sharp, the characters were all completely settled into their personas, and this episode proved why people needed to pay attention to what was one of the smartest comedies on television.

16 "Halloween"

Season 1, Episode 6

The first "Halloween" episode in Brooklyn Nine-Nine history helped set the table for one of the fan-favorite traditions on the show. This introduced the annual "Halloween Heist," which went on to become one of the most beloved aspects of the show. With the holiday upon them, Jake and Captain Holt decide to match wits with a friendly competition as Jake bets that he can steal Holt's Medal of Valor before midnight.

The heists got really creative as the seasons wore on with some of the later episodes having trumped this one in many ways, but seeing the first season's heists was still fun and creative. It is the kind of entertaining and fast-paced storytelling that makes it clear why this became a recurring gag. This was also the first episode to have the "title of your sex tape" joke, making it even more iconic.

15 “The Jimmy Jab Games”

Season 2, Episode 3

Towards the beginning of season 2, audiences saw the ultimate team-building exercise from the Nine-Nine with the "Jimmy Jab Games." With Terry and Holt out of the office, Jake suggests this competitive yet comical set of games that test each member of the squad's skillsets. The games range from eating expired Chinese food to going undercover. The prize on the line is Jake's chance to get the phone number of Rosa's friend, but it seems like his heart is elsewhere.

Not only was the episode filled with hilariously disastrous moments, but it was also the episode where Jake realized and admitted to Rosa that he still had feelings for Amy, thus setting the stage for the best relationship in Brooklyn Nine-Nine. This was also the episode where Madeline Wuntch proved to be a strong member of the cast, and her insults were harsh and hilarious, setting up her antagonistic role in the future.

Related Brooklyn 99: Why Chelsea Peretti's Gina Left The Show Chelsea Peretti shocked fans when she announced her exit as Gina in Brooklyn Nine-Nine, but why did she really leave the popular NBC sitcom?

14 “Pimemento”

Season 7, Episode 3

The main cast of Brooklyn Nine-Nine makes up one of the most beloved ensembles in television history. However, as funny as they are, there are some supporting characters who have managed to come in and steal the show with Adrian Pimento being considered one of the funniest side characters on Brooklyn Nine-Nine.

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, setting up a Memento scenario.

Jason Mantzoukas is an actor who has been hilarious on a number of shows, from The League to The Good Place to Parks and Recreation. He seems to be having a lot of fun bringing this wild new character to Brooklyn Nine-Nine. Pimento is an intense cop who seems like the stereotypical hero seen in action movies but fits into the absurdity of the Brooklyn Nine-Nine world.

13 “HalloVeen”

Season 5, Episode 4

Close

As the Halloween Heist episodes of Brooklyn Nine-Nine began to become more cemented in the show's legacy, the show would continue to try and up the ante with each new installment. Season 5 attempted to keep audiences on the edge of their seats and surprise them which proved difficult the more heist episodes they delivered. However, while waiting to see who was going to be crowned the "Ultimate Detective/Genius," this heist episode delivered something different.

In the end, this was actually a Jake and Amy episode of Brooklyn Nine-Nine disguised as a Halloween episode. Amid all the chaos of the competition, Jake proposed to Amy. As strong and likable as their relationship had been up to that point, this was a shock, brilliantly delivered by the show. The heist aspects were still entertaining but it made for a heartwarming ending.

12 “Cop-Con”

Season 4, Episode 18

Close

In this season 4 episode, the squad goes to Rochester for Cop-Con, a police convention. While Holt is giving a presentation at the convention, the rest of 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. This was a giant ensemble piece, it showed how great these characters are when they're all together. Plus, the formula was a tried and true one in projects like The Hangover and Dude, Where's My Car?

It is also another episode that has a lot of fun with getting the characters out of the typical setting and cutting loose on a getaway. There is also a funny and sweet subplot with Amy and Gina attempting to help Hitchcock in his pursuit of a new love interest.

11 “Moo Moo”

Season 4, Episode 16

Brooklyn Nine-Nine has a great 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. However, for Terry, it still was a major problem that needed to be reported.

This is something that became more of an issue for the show as it went on. With more controversy and discussion surrounding real-world policing practices, it posed a tricky thing for a funny sitcom set in this world to address. The way the writers tackled this very real issue that happens all the time was respectful and rather poignant. Crews, in particular, gives a good performance which helps to sell the message of the episode.

10 "Johnny And Dora"

Season 2, Episode 23

Close

From the beginning of the series, it wasn't hard to predict that Jake and Amy would ultimately end up together, but watching that romance bloom was one of the most entertaining aspects of the early seasons. Following several hurdles that included an undercover operation and ill-timed relationships, Jake Peralta and Amy Santiago were finally single at the same time. Santiago, however, declared no more relationships with cops just as Jake was about to make his move.

They awkwardly went undercover as a newly engaged couple, "Johnny and Dora," resulting in a couple of fake make-out sessions before Jake and Amy's first official kiss, igniting the spark between them. This episode featured an emotional moment from Detective Raymond Holt, who was forced to leave the Nine-Nine by his recurring nemesis Madeline Wuntch to save his squad from being split up.

9 "Yippie Kayak"

Season 3, Episode 10

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 many hilarious episode gags. The series even had a guest appearance from Die Hard original cast member Reginald VelJohnson.

However, it was season 3 that hilariously put Jake and others inside of a real Die Hard scenario. Season 3 saw Peralta, Charles Boyle, and Gina Linetti trapped in a department store hostage situation on Christmas, poised to re-enact Jake's favorite film.

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. It was a hilarious way of paying homage to one of the greatest action movies of all time in classic Brooklyn Nine-Nine fashion.

Related Brooklyn Nine-Nine: 10 Iconic Quotes Fans Didn't Know Were Improvised Brooklyn Nine Nine has remained a fan favorite sitcom even after finishing its run, but how how many iconic quotes were improvised?

8 "The Pontiac Bandit"

Season 1, Episode 12

It's difficult to pick the best guest star on the series, but Craig Robinson is certainly a fan favorite. Craig Robinson's annual Doug Judy appearances are beloved by fans, as watching his and Jake Peralta's friendship develop was just as rewarding as Jake and Amy's 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. Robinson steals the show as a genuinely charming thief who just seems to be having a good time.

7 "Jake And Amy"

Season 5, Episode 22

Season 5 of Brooklyn was building toward 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. It sets the stage for a dramatic sitcom wedding episode with some big laughs and a lot of heart.

While the season-long planning of the wedding was ruined, 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, considering the series was canceled by Fox shortly after this aired. However, had this really been the last episode of the series, it would have ended with a great example of the show's mixture of sweetness and humor.

6 "Game Night"

Season 5, Episode 10

Close

Inspired by Stephanie Beatriz 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, 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. It was a standout episode for Beatriz who brought more vulnerability to Rosa than had previously been seen on the show.

The episode featured a touching scene between Beatriz and Trejo as the father accepts his daughter, and also showcased Jake and Diaz's friendship and Peralta's continuing growth into a mature and responsible adult. Not only is this one of the best Brooklyn Nine-Nine episodes, but it also helped demonstrate why Brooklyn Nine-Nine won the GLAAD Media Award for Outstanding Comedy Series in 2018.

5 "The Bet"

Season 1, Episode 13

Going back to the pilot episode of Brooklyn Nine-Nine, the stakes were set in place for this episode. It was the culmination of a season-long bet over who is the better detective, Peralta or Santiago. The wagers were Jake's prized 1965 Ford Mustang versus Amy having to go on the worst date ever in Jake's Mustang. Though the two had been set up as bickering rivals leading up to this moment, things started to change when the winner is revealed.

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 few seasons until those feelings were fully realized.

4 "The Last Ride"

Season 4, Episode 15

While Brooklyn Nine-Nine faced cancelation a few times in its run, the characters of the show are faced with an uncertain future in season 4. 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 10 hours, and Sergeant Jeffords with Diaz battles against Hitchcock and Scully for the precinct arrest record.

In true Nine-Nine fashion, the precinct is saved by Gina's live streams that captured numerous moments of hilarious cement drinking pranks and an impassioned speech by Holt when Peralta and Boyle decided to go for the bigger bust. The episode features great moments from the entire squad and perfectly exemplifies the depths the show can reach.

3 "Show Me Going"

Season 5, Episode 20

Close

An episode that proves the show isn't all about comedy is season 5's "Show Me Going," which features the squad dealing with the news that Diaz is involved in an active shooter situation that 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 to help Diaz, and instead does the right thing and chooses to be there for the Nine-Nine until Diaz' safe return.

It is another reminder of the tricky situation Brooklyn Nine-Nine was often in with its choice of setting. It was often a silly comedy show, but something it had to address was the dangers of this job. It was an emotional episode that highlighted the deep relationships this team developed with one of the least emotional members of the team.

Related Everything Stephanie Beatriz Has Done Since Brooklyn 99 Stephanie Beatriz has had a career explosion since Brooklyn 99, starring in Disney musical movies and voicing characters in numerous animated shows.

2 "Halloween II"

Season 2, Episode 4

Brooklyn Nine-Nine is known for every season's recurring themed episodes, such as the annual heist-based Halloween episodes. While it's hard to pick the best Brooklyn 99 episodes at Halloween, "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. Andre Braugher's performance was indeed the highlight of this episode and started the hilarious growing trend where this usually stoic and professional captain becomes obsessive about these annual competitions, taking them to a wild degree of intensity.

1 "The Box"

Season 5, Episode 14

It is always fun to see a show that has a winning formula worked out decide to take some risks with a different kind of episode. "The Box" features Holt and Peralta locked in an intense interrogation against one of the best guest stars to hit the Nine-Nine, Sterling K. Brown. While viewers have seen police interrogations before, none compare to the mind games witnessed 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 into 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. It is a wonderful episode that shows the evolution in Jake and Holt's relationship. Brown is excellent in the villainous role and Braugher has some terrific moments of combining his amazing dramatic talents with his comedic ones.