Police procedurals and workplace comedies have consistently dominated network television, and Brooklyn Nine-Nine brilliantly combined these genres with its humorous portrayal of a fictional precinct in the New York Police Department (NYPD). The series followed a diverse ensemble of detectives tackling the city’s criminal underbelly, focusing particularly on the strict yet lovable Captain Holt and the laid-back detective Jake Peralta (Andy Samberg). Premiering in 2013 on Fox, the show later transitioned to NBC, concluding in 2021 after a successful run of eight seasons and over 150 episodes that captivated audiences.
Brooklyn Nine-Nine maintained a high standard throughout its airing, showcasing not just comedic brilliance but also profound storytelling. Some of its finest episodes artfully balanced humor with serious themes, addressing critical issues with sensitivity. Regardless of the episode’s tone, the most unforgettable moments featured characters at their most compelling and amusing, whether they were racing to apprehend a suspect or indulging in their usual comedic escapades.
10
“The Party”
Season 1, Episode 16 (2014)
At Captain Holt’s birthday celebration in the episode titled “The Party,” the squad attempted to leave a positive impression on his husband, Kevin (Marc Evan Jackson), who serves as the head of the classics department at Columbia University. As various members of the squad faced challenges to connect, Charles (Joe Lo Truglio) found an unexpected connection with Vivian Ludley (Marilu Henner), an older woman and a colleague of Kevin’s. Initially, it appeared that Holt was reluctant for them to join the celebration, but it was actually Kevin’s past experiences with police homophobia that made him hesitant.
Among all the couples depicted in Brooklyn Nine-Nine, Holt and Kevin’s relationship stands out as one of the most endearing aspects of the show. Their compatibility and deadpan humor provided endless entertainment. Although the storyline of the squad striving to impress the sophisticated Kevin felt somewhat clichéd—which is typical in sitcom narratives—it was executed with great finesse. This episode also offered a delightful glimpse into Holt’s life beyond the precinct, enriching the viewer’s understanding of his character.
9
“The Last Day”
Season 8, Episodes 9 and 10 (2021)
In the two-part series finale titled “The Last Day,” the squad reminisced about their eight years of camaraderie while anticipating their future as both Holt and Amy (Melissa Fumero) prepared for new roles after being promoted to lead their reform initiatives as Deputy Commissioner and Chief, respectively. The team also embarked on one last heist—the victor would earn the prestigious title of The Grand Champion of the Nine-Nine, and Jake announced his intention to leave the precinct.
“The Last Day” served as a bittersweet yet fulfilling conclusion to Brooklyn Nine-Nine, showcasing the essence of what a sitcom finale should encapsulate. Each character received a heartfelt sendoff, including some of the series’ most beloved recurring figures. The episode was filled with delightful nods to fans, including fantastic callbacks and the most intricate heist in the series’ history. The narrative came full circle while leaving enough room for the characters’ journeys to continue.
8
“Jake and Amy”
Season 5, Episode 22 (2018)
Despite Amy’s meticulous planning, the wedding day for Jake and Amy was disrupted by a bomb threat in the Season 5 finale titled “Jake and Amy,” with the head of the bomb squad turning out to be Amy’s ex-boyfriend. As the rest of the Nine-Nine scrambled to manage last-minute wedding details, Holt received an email that would reveal whether he had secured the commissioner position, while Rosa (Stephanie Beatriz) found a connection with a ride-share driver.
In true Brooklyn Nine-Nine fashion, no sitcom wedding is complete without chaos, and Jake and Amy’s special day was no exception—everything that could possibly go wrong did. Nevertheless, the episode culminated in a heartfelt season finale, granting the couple the beautiful wedding they truly deserved. The cliffhanger ending regarding Holt’s promotion to commissioner added an intriguing layer to the narrative, making it a memorable finale.
7
“Coral Palms”
Season 4, Episodes 1-3 (2016)
In the Season 4 premiere titled “Coral Palms,” Jake and Captain Holt found themselves in a precarious situation as they entered witness protection under the threat of Jimmy “The Butcher” Figgis (Eric Roberts) seeking to kill them. Determined to return to their lives and loved ones in New York, they devised a plan to lure Figgis out while attempting to apprehend him independently. However, their efforts backfired, prompting the entire Nine-Nine to rush to their aid. This gripping narrative unfolded over three thrilling episodes.
The entire “Coral Palms” narrative arc was a delight to watch, making it a challenge to pinpoint a single standout episode. Holt and Jake’s lives in Florida offered a refreshing change of scenery, showcasing their adaptability beyond police work. One of the highlights was a memorable guest appearance by Maya Rudolph, who portrayed Jake and Holt’s handler, adding another layer of hilarity to the episodes.
6
“9 Days”
Season 3, Episode 12 (2016)
In the episode “9 Days,” Jake and Holt found themselves in quarantine after contracting the mumps while investigating a cold case. They were confined to Holt’s home, determined to solve the case despite their discomfort. As they dealt with painful goiters and the side effects of cold medicine, they experienced a breakthrough in their investigation. Meanwhile, Terry (Terry Crews) took over the precinct, trying to manage a list of urgent repairs, while Charles mourned the loss of his beloved dog.
“9 Days” was filled with memorable moments—the dynamic between Jake and Holt as they spent days together in quarantine created a treasure trove of comedic and character-driven interactions, especially as their illness and self-medication amplified their antics. The episode not only stands out as one of the best in the entire series but also serves as a particularly notable showcase of Holt, whose typically deadpan demeanor contributed to some of the episode’s most hilarious scenes. The chaos at the precinct added an equally entertaining subplot.
5
“The Safe House”
Season 5, Episode 12 (2018)
After a serious threat to Kevin’s life from Seamus Murphy (Paul Adelstein), Holt made the decision to send Kevin to a safe house under Jake’s protection until they could solidify a case against Murphy. Holt’s overwhelming concern for Kevin’s safety resulted in a series of over-the-top rules, such as banning internet use and requiring them to crawl through the house to avoid detection. Meanwhile, Charles and Rosa undertook a covert operation at a hair salon to gather information on Murphy from his girlfriend.
Some of the most memorable episodes of Brooklyn Nine-Nine feature characters forced together, as seen in “9 Days,” but “The Safe House” elevated this dynamic with a series of side-splitting moments. The interplay between Kevin and Holt was always enjoyable, and their chemistry was heightened by Holt’s stringent regulations. However, what truly shone was the comedic rapport between Kevin and Jake, which provided an additional layer of entertainment.
4
“HalloVeen”
Season 5, Episode 4 (2017)
The annual Halloween heist at the precinct had everyone plotting and scheming against each other in a bid to win a championship belt—or as Holt insisted on calling it, a “cumberbund”—entitled “Amazing Human/Genius” by midnight in the episode “HalloVeen.” The episode reached a thrilling climax when Jake revealed that the heist was a ruse to propose to Amy, with Charles being one of the most enthusiastic supporters of the proposal.
The Halloween heist episodes consistently rank as highlights of the series, making it challenging to determine which one reigns supreme. Like previous Halloween-themed episodes, “HalloVeen” was laden with intricate plans and betrayals, delivering a satisfying conclusion, but it distinguished itself by utilizing the heist as an elaborate backdrop for Jake’s heartfelt proposal to Amy. This combination of humor and sweetness marked a significant milestone in their relationship.
3
“The Suicide Squad”
Season 6, Episode 18 (2019)
In a quest to dismantle Commissioner John Kelly’s (Alan Brooks) illegal Stingray operation, which involved spying on innocent citizens, Jake assembled an unconventional team of police officers, incorporating former adversaries—Wuntch (Kyra Sedgwick), the Vulture (Dean Winters), and C.J. Stentley (Ken Marino)—in an episode dubbed “The Suicide Squad,” the second part of the thrilling Season 6 finale. The plan was to stage a kidnapping, yet the execution spiraled into chaos due to a combination of incompetence and distrust.
Brooklyn Nine-Nine’s rendition of a Suicide Squad delivered laughter as it united some of the NYPD’s most colorful personalities—resulting in hilariously chaotic interactions. Each character added their unique flair, but together they exacerbated each other’s flaws, creating comedic gold. Even as everything seemed to unravel, they ultimately managed to achieve their objectives in a brilliantly entertaining manner.
2
“The Cruise”
Season 3, Episode 13 (2016)
In the Season 3 episode entitled “The Cruise,” Jake and Amy embarked on their first vacation together aboard a cruise ship, only to discover that the ship’s entertainment featured none other than Doug Judy (Craig Robinson), Jake’s long-time nemesis. Judy revealed he was under threat from an assassin and had orchestrated their presence on the cruise to seek their help. Meanwhile, back at the precinct, Holt dealt with a visit from his sister, Debbie (Niecy Nash).
Every episode featuring Doug Judy is a standout—his antics and undeniable chemistry with Jake consistently entertain. However, “The Cruise” shines brightly not only within Doug Judy’s arcs but also throughout Season 3, thanks to its engaging humor and captivating premise. The writers expertly introduced Judy into Jake and Amy’s vacation narrative, making it a humorous and unexpected twist.
1
“The Box”
Season 5, Episode 14 (2018)
In the episode “The Box,” Jake and Holt—who had planned to attend an opera—found themselves spending their evening interrogating Phillip Davidson (Sterling K. Brown), a dentist accused of murdering his partner, who had seemingly covered his tracks meticulously. As they struggled to provoke a slip from him or at least obtain an admission of guilt, the tension escalated between them, resulting in disagreements over their tactics while Phillip toyed with their efforts.
While “The Box” included its share of humor, what truly distinguished it was its gripping plot and its effectiveness as a police procedural. Phillip emerged as one of the most memorable and unsettling villains in the series—his cold, calculated demeanor was masterfully portrayed by Brown. Jake and Holt’s dynamic in this intense scenario showcased their contrasting styles while working effectively together.
