10 Most Rewatchable Episodes Of Brooklyn Nine-Nine

"Brooklyn Nine-Nine" is both one of the best comedy TV shows of all time, and one of the best cop shows ever made. Those themes don't always go together well — after all, cops are meant to deal with life's gritty realities. But "Brooklyn Nine-Nine" still manages to find the fun and the joy in the day-to-day lives of a group of New York detectives. 

The show starts off with a strong ensemble that stays largely the same for its eight season run, led by Jake Peralta (Andy Samberg) — a goofy detective with superb intuition and a penchant for hijinks — and Captain Raymond Holt (Andre Braugher), a longtime officer whose fastidious, high-caliber work has been opening doors for marginalized cops since the '70s. Captain Holt's introduction as the 99th's new commanding officer is the instigation for the series' pilot, and his relationship with Jake is quickly established as the centerpiece of the show.

"Brooklyn Nine-Nine" is packed tight with jokes. Only a series like "30 Rock" or "The Good Place" could challenge it in a competition to see which series has a higher density of good bits. The sheer amount of comedy makes it the perfect show to rewatch, because it's always possible to catch a joke you never noticed before. The series is also notable for its fun cast of characters, including: Gina Linetti (Chelsea Peretti), Amy Santiago (Melissa Fumero), Charles Boyle (Joe Lo Truglio), Sergeant Terry Jeffords (Terry Crews), and Rosa Diaz (Stephanie Beatriz).

Fans of "Brooklyn Nine-Nine" will quickly identify Halloween as a special holiday for the 99th precinct. The first season episode, "Halloween," marks the beginning of the Halloween Heist tradition, and it's one that escalates by leaps and bounds every year. 

We've since ranked every Halloween heist episode of "Brooklyn Nine-Nine," and while Season 1's offering isn't the best, it is the origin story for the annual event. Only six episodes into the series, Jake decides to challenge his new boss. Jake claims that he can steal Captain Holt's medal of valor before midnight, as the calendar turns to November 1st. If Holt fails to protect it, he has to do all of Jake's paperwork for a week. If Jake loses, he has to work a week of free overtime.

While Jake still embraces his natural affinity for drama in his pursuit of the medal, he doesn't come up with a scheme that is nearly as complex as the heists will be in following seasons. It's fun to rewatch this episode because it seems so tame compared to later shenanigans. Plus, Holt is thus far unaware of how far Jake is willing to go in order to get that medal. 

Jake's main advantage is his secret recruitment of the whole detective squad, whose paperwork he's promised to do in exchange for help. After Jake wins the bet, Holt has to do the entire squad's paperwork in his stead. Watching this episode can lead to a full rewatch of every Halloween heist episode, and that is a very fun mini-marathon.

One of the most underrated episodes of "Brooklyn Nine-Nine" is the season 2 episode, "Beach House." It follows everyone as they get together at Boyle's beach house for drinks, gossip, hot tubbing, relaxation, and fun. Normally, the retreat is meant only for detectives, but after Captain Holt confides in Jake that he wasn't able to enjoy time with his own coworkers when he was a detective due to unapologetic racism and homophobia, Jake invites him along. This effectively ruins the squad's no-boss vacation.

Holt is about as highbrow and boring as someone can be. His favorite color is tan (it's no-nonsense), he hates chocolate because it has "too much taste," and he's produced more than 300 still-life paintings of the same gray rock. 

The squad is not happy to have Holt at their getaway due to his lack of fun, and because Holt is their boss. Amy is particularly nervous because she promised Gina she would attempt to reach one of her buried identities via six drinks. 

Amy's many drunken inner selves are a running gag for the entire series, and she later discovers that eight-drink Amy speaks French and nine-drink Amy is an equestrian. Holt is bummed when he realizes the squad isn't happy to have him at the beach house, but after Jake suggests he stoop to their level, viewers get one of "Brooklyn Nine-Nine's" funniest moments.

"Ava" is a great episode that offers lots of opportunities for characters to break from their usual rhythms. Terry and his wife, Sharon (Merrin Dungey), are expecting their third child and about to go on one last getaway before the baby comes. Terry and Rosa also need to interrogate a prison inmate, so Terry asks Jake to take care of Sharon when she arrives at the precinct before they depart for their trip. 

Predictably, Sharon's water breaks shortly after she arrives, and she is adamant that she won't go to the hospital after a bad experience there. To make matters worse, the internet in the precinct is down, so Charles and Amy have to file a mountain of paperwork by hand, and there's a large group of citizens who can't leave before the processing is done.

Jake does a great job taking care of Sharon amidst the chaos. Holt acts out in petulance and pettiness due to Jake's disclosure that Sharon feels uncomfortable around him. There's a reason Holt is the show's not so secret weapon, and it's because he is both perfect and flawed. 

Some of Holt's best jokes are delivered in moments of rich, unpredictable emotion that viewers rarely get to see from the otherwise composed man. The episode finds other characters well out of their comfort zone, too. In addition to Jake and Holt, audiences get a hyper-focused Charles and a discouraged Amy. We see Gina forced into a caretaking role for Sharon, and a frantic Terry desperately rushing through the city to see the birth of his daughter. "Ava" also features a great little guest spot from Nick Offerman as Holt's OB-GYN ex-boyfriend.

Doug Judy (Craig Robinson) features a huge transformation throughout "Brooklyn Nine-Nine" despite appearing roughly once per season. Initially, Judy is revealed to be Jake's criminal nemesis, the Pontiac Bandit. He regularly escapes custody and accountability, much to Jake's frustration. 

Doug and Jake have tons of platonic chemistry and as such become friends throughout the course of the show, so much so that Doug is eventually able to have his record cleared and live a life without crime. Every episode that features Doug is worth watching, but "The Cruise" offers the perfect balance between Doug and Jake as rivals, and Doug and Jake as friends.

Jake and Amy, who have been dating for a few months, go on a cruise only to discover that Doug is the ship's lounge entertainer. Turns out, Doug sent Jake the free trip so that Jake would come and protect him, because someone aboard is allegedly there to kill Doug. 

Jake is indignant, demanding that Judy remain with him and Amy 24/7 until they return to New York and Jake can take him into custody. That plan doesn't work out, but he and Amy do save Doug's life. Even though Doug then escapes, Jake and Amy get to say "I love you" at the end of the episode. Be sure to keep an eye out for a cameo from Paul F. Tompkins as the cruise ship's tax evading captain.

Comedic actor Jason Mantzoukas is a sitcom gem, having stolen many a scene as a guest performer. His best spot, though, is definitely on "Brooklyn Nine-Nine," in which he plays a detective named Adrian Pimento. 

Pimento shows up at the 99th precinct after spending several years undercover working for Jimmy "The Butcher" Figgis (Eric Roberts), a powerful New York City crime boss. It quickly becomes clear that Pimento's time undercover has made him incapable of functioning as a regular person. Adrian's story sounds dark, but Mantzoukas is a whimsical performer who infuses Pimento with raw positivity and a frenetic, outgoing energy that helps him find the funny in every scene.

Jake, who went undercover for a few months with the Italian mafia, attempts to take Adrian under his wing, only to realize that Pimento's experience is unfathomable compared to his own. Ultimately, Jake offers his friendship and support even though he can't understand everything that Adrian is going through. 

While that's going on, Charles runs a volatile cooking experiment that forces him to grovel before the building's custodial staff (led by Kate Flannery's Marge), and Gina directs Holt and Rosa in a video submission for the M.C. Guffin foundation. Gina recasts Holt and Rosa after they fail to impress on camera, and Charles, Amy, and Terry ultimately gain Marge's favor. The episode definitely belongs to Pimento, though, and it arguably makes up for the fact that Mantzoukas was originally eyed for Detective Boyle.

"Brooklyn Nine-Nine" doesn't offer many bottle episodes throughout its run, but Season 5's "The Box" may be one of TV's best examples ever. According to IMDb, "The Box" is the show's highest rated episode, and it's not difficult to see why — especially if you're a fan of Andre Braugher's previous work, "Homicide: Life on the Street," and remember the Emmy-winning episode "Three Men and Adena." 

The episode follows Jake and Holt as they go through a painstaking interrogation with a murder suspect named Philip Davidson, played by Sterling K. Brown. Brown is chilling as a drug-addicted dentist who orchestrated the murder of his business partner. At the beginning of the night, Holt cancels his plans and stays to participate in Jake's interrogation.

"The Box" tests Holt's wishy-washy confidence in Jake, with Philip proving to be a cool, collected adversary that the pair can't seem to rattle into giving a confession. Holt and Jake's working relationship is tested as Holt grows more and more concerned that Jake won't be able to nail the interrogation, and because their relationship is so rich and central to the show, "The Box" feels full despite depicting only one plot line. 

Ultimately, Jake is able to get a confession from Philip by empathizing with him, realizing that Philip can't handle an insult to his murderous brilliance. This episode provides one of Jake's best moments in all of "Brooklyn Nine-Nine" when he secures a confession at the last minute and earns massive props from Holt.

Most modern sitcoms offer audiences a will-they-or-won't-they romance, thanks to the legacy left behind by shows like "Friends," and "The Office," so it's not surprising that "Brooklyn Nine-Nine" finds its own version of the trope in the relationship between Jake and Amy. 

At first they seem like incompatible opposites: Jake is messy and unconcerned with rules, while Amy is compulsively put together and so rule-abiding that she won't change lanes without putting on her turn signal. But Jake and Amy are both smart detectives and good people. They become a fantastic couple, and Season 5's "Jake and Amy" is one of the most satisfying sitcom wedding episodes of all time.

It's not just the tension bottling inside of Amy, or the myriad things that go wrong setting up the ceremony. Early in the episode, they receive a call that someone has planted a bomb at their wedding. The threat effectively halts the day's events, and just as Jake and Amy are agreeing to visit City Hall the next day for a quick ceremony, the squad reveals that they've set up a new venue for the couple outside the precinct. 

Holt officiates and a bomb-diffusing robot serves as ring-bearer in the makeshift wedding, and fans are treated to a beautiful exchange of vows. It's one of Amy and Jake's best moments on "Brooklyn Nine-Nine," for sure.

Unlike many sitcoms, "Brooklyn Nine-Nine" thrives in offering some of the worst (yet best) villains of the genre. After discovering that police commissioner Kelly (Phil Reeves) has initiated the use of illegal surveillance technology to spy on New Yorkers, Jake and Holt decide to take action, with Jake gathering a "Suicide Squad" of the biggest dirtbags in the NYPD. 

This episode finds the team joining forces with The Vulture (Dean Winters), Captain C.J. (Ken Marino), and Madeline Wuntch (Kyra Sedgwick), all of whom have unleashed setbacks on the squad and earned laughs from fans. Holt is especially disgusted to be working with his sworn enemy, Wuntch, but Jake is insistent that they need her help to stop Kelly.

Luckily for everyone, Jake knows Holt won't trust Wuntch that easily, and he secretly devises a plan that will prove successful — so long as Holt knows nothing about it. Just when it seems like Madeline has met Holt's expectations and betrayed him, she reveals that she and Jake were working together all along. It's fun to see so many great guest stars in one episode, and "Suicide Squad" proves, for the sixth time in a row, that "Brooklyn Nine-Nine" knows how to put on an impeccable season finale.

Another fantastic finale episode, "Lights Out," finds the squad responding to a surprise city blackout. Amy, whose maternity leave was set to begin the following day, is forced to take charge during the crisis when they discover that Holt and Terry are stuck in an elevator.

Amy, whose water breaks shortly after the blackout hits, literally runs the station's emergency response while in labor, and Rosa is the only one there to provide emotional support. Meanwhile, Terry teaches a choreographed dance to Holt in the elevator in order to distract the Captain from his childhood fear of shoddily inspected elevators.

Outside, Jake and Charles discover and apprehend a drunk driver that crashed into a transformer, but are unable to transport him back to the police station due to bumper-to-bumper traffic. They decide to go on foot, and along the way they encounter hilarious situations, including a surprisingly aggressive old woman named Dottie (Jill Basey) and a pedal pub (a beer party on a multi-seated bike) full of drunken bachelorettes. 

When Jake discovers that Amy is in labor, he does everything he can to get to the hospital only to discover that Amy has waited too long and will have to give birth at the precinct. Thanks to an assist from Charles' nemesis, a horse name Sergeant Peanut Butter, Jake arrives at the station just in time to see the birth of his son.

Even though there's already a great Doug Judy episode on this list, his relationship with Jake is so rewarding that we had to include Season 8's "PB & J," Doug's final appearance on the show. Craig Robinson is one of "Brooklyn Nine-Nine's" best guest stars, thanks to his character's star-crossed friendship with Jake. It makes sense then, that Jake is devastated to discover that Doug has been arrested for an outstanding warrant in New Jersey.

Jake offers to transport Doug to prison so they can have one last hurrah. He gets them matching rings and jumpsuits, signs out a super cool car from the precinct, and manages to predict all of the snacks that Doug wants to have before he is forced behind bars. Doug still takes the opportunity to escape custody; even though he loves Jake, he doesn't believe that Jake's job is more important than his freedom. 

Unfortunately, the goons that his sister, Trudy (Nicole Byers), hires to keep him out of jail intend to kill Jake. Doug would never let his buddy die, and he sacrifices his chance to escape to save Jake's life. At the end of the episode, Doug calls Peralta to reveal that he is in Amsterdam, having escaped after all. 

For the first time in their entire relationship, Jake broke the law for his friend. He slipped Doug a pen before they parted, knowing that Doug could use it to free himself. Jake ultimately chooses love over the job, and "PB & J" provides the perfect ending to the series-long saga of Jake Peralta and the Pontiac Bandit.