Brooklyn Nine-Nine was remarkably consistent during its run, and the best Brooklyn Nine-Nine 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 Nine-Nine 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 Nine-Nine 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. The show was often at its best when it blended comedy with serious subject matter in a way few series could.
Brooklyn Nine-Nine has won multiple awards, including Golden Globes, Critics' Choice, GLAAD Media, and Creative Arts Emmys
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25 "Ding Dong"
Season 7, Episode 7
"Ding Dong" had an interesting moment for Brooklyn Nine-Nine fans. One of the best antagonistic relationships in the series came between Captain Holt and Madeline Wuntch, played brilliantly by Kyra Sedgwick. Their back and forth, and her catttiness, made the two a treasure to watch whenever they attempted to one up each other. However, shockingly, this episode opens with the precinct learning that Madeline has died.
By the time the memorial comes, Holt got the last laugh
The funny moments started from the beginning, with Holt incredibly happy she was dead, buying bagels for everyone in celebration, and even taking selfies with her dead body at the funeral home. However, she had one last way to get him in the end. She asked that he organize her memorial, knowing he would speak badly of her and damage his own career. By the time the memorial comes, Holt got the last laugh in one of season 7's best episodes.
24 "He Said, She Said"
Season 6, Episode 8
"He Said, She Said" in season 6 was one of the Brooklyn Nine-Nine episodes that took a look at a real-life tough situation, but did it with humor and sincerity at the same time. In the episode, a woman accuses her boss of sexual harassment. The twist is that she "broke his penis" while rebuffing his advances. When she is offered a large sum of money to sign an NDA and not come forward with the case, Amy convinces the woman not to take the deal so they can bring him down.
This sees Jake put in the middle of the entire situation and shows how oblivious he is to what the women go through every day, with Amy giving specific examples of how people treat her and Jake differently. However, the episode takes a turn for the serious when Rosa comes in and explains that Amy demanding to focus on the case could hurt the woman more than it helps her. All the while, Jake, as a man, is hearing things he never dreamed of and the episode is all the better for it.
23 "Adrian Pimento"
Season 3, Episode 17
This episode introduces fans to Adrian Pimento, a detective who returns after being undercover for 12 years while working for Jimmy "The Butcher" Figgis. Played by Jason Mantzoukas, this might be one of the best guests to ever appear on Brooklyn Nine-Nine, as his wild-eyed and paranoid disposition makes him a perfect actor to really eschew the tropes of a police procedural. Every time he appears on the show, it is sure to be a wild ride and this first appearance is no different.
The series has him playing a tortured cop to perfection as he deals with PTSD after doing so many bad things to keep from blowing his cover over the years. Having Jake begging to work with Adrian, it was a perfect match between the polar opposites as they work a robbery case. There was also a hilarious subplot where Charles has to deal with an angered head of custodians, played by The Office's Kate Flannery.
22 "The Fugitive"
Season 4, Episode 11-12
"The Fugitive" is a two-part episode from season 4 that does a lot in its running time. In these episodes, a prison van crashes and the prisoners escape, leading the police on a manhunt to bring them back in. The second episode also leads Jake to approach an unlikely source to get information. This is a fun moment as Jake offers his nemesis Judy (Craig Robinson) immunity if he helps them catch one last inmate. Anytime Judy shows up, it is a treat, and this time was no different.
What makes it work so well is that Jake allows Amy to get the last arrest so she can win.
This is also an important turning point in Amy and Jake's relationship. They had been talking about moving in together. With the prisoners escaping, the two make a bet with each other that whoever catches the most escaped prisoners gets to be whose place the other moves into. What makes it work so well is that Jake allows Amy to get the last arrest so she can win, as he makes the selfless decision to move in with her. It was a nice moment that showed their growth as characters.
21 "Bad Beat"
Season 5, Episode 5
Some of the best Brooklyn Nine-Nine episodes deal with things other than hilarious jokes and attempts at humor. That is the case with "Bad Beat," although the episodes has some very funny moments. In this one, Jake, Terry, and Holt head out to start working on a new operation, but there is one problem. They need to go undercover at an underground gambling ring. The problem is that Holt is a gambling addict. While he has overcome this addiction, he is worried it will creep back out again if he goes in.
The show works really well because it takes the gambling addiction seriously, and doesn't really use it as a big joke to mock the condition. When Holt enters Gamblers Anonymous, he takes a realistic positive step in getting better. There were also funny moments, including Amy starting a food truck business, but it is Holt's storyline that remains quality. In a review for The A.V. Club, their critic wrote that "It's also another episode that fully utilizes every available cast member."
20 "Pilot"
Season 1, Episode 1
It's impossible to look at the best Brooklyn Nine-Nine 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.
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.
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.
The woman only remembers that the killer sang a Backstreet Boys song
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
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 Jake 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 Nine-Nine 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.
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
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
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 use 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 Hitchco*ck 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
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.
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
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.