30. The Wednesday Incident
Season 2, Episode 16
First of all, Garry Marshall is an excellent cameo or guest star in everything he does, from Hocus Pocus to this episode of Brooklyn Nine-Nine as a truly awful geriatric criminal that has Rosa and Amy fooled, much to Boyle’s frustration. But secondly, this is just a really strong episode focusing on Kevin and Holt’s strange, but strong relationship. Communication is the key to any lasting love, and that is the ultimate moral of the story. Future-Wife, I’m sure you are reading this, but if I ever get stabbed while defending myself from muggers, I promise to tell you.
29. AC/DC
Season 2, Episode 20
After injuring himself trying to be an action movie star, Jake takes a much-needed guys trip with his best bud Boyle. But much to Charles’s dismay, Jake prompted the guys trip just as a ruse to continue following a case that he’s been forced to drop. But it’s Jake’s reasoning why he kept pursuing the suspect that is so powerful. He has the deaths of two civilians on his conscious since the last time he left a case open to go party with friends. It’s one of the biggest regrets of his career, and one that he needs support getting through. Very few comedies let their characters have regrets with major stakes, and Jake’s regret in this episode just shows how much he has already been affected by the squad under Holt’s guidance.
28. The Cruise
Season 3, Episode 13
Doug Judy makes Jake a better man, despite one being a cop and the other a major criminal. But can other major criminals effectively moonlight as Cruise Ship lounge singers? I THINK NOT! The moment of the episode though is, after much headbutting in how to spend their pseudo-vacation, Jake finally says I love you too Amy! It’s also how it’s written that I found so touching. After Amy says ‘I love you’ to Jake, he can only muster up an uncomfortable “Noice. Smort!” But he realizes, in the moment, that that was not what he meant to say. And he swallows his fears and looks Amy in the eyes and says it back to her. Sometimes love is written to be far more complex and precious than it really is. Love is simply listening to yourself, and openly expressing that to the person you feel this for. Take from me: a man who is about to successfully get married!
Also, I absolutely love Niecy Nash in everything she does, but especially as Holt’s little sister. Despite her personality clashing with Holt, their reconciliation at the end of the episode really goes a long way to show how versatile Andre Braugher is as a comedic actor. He’s been nominated for this role in the past, but it’s a shame that he’s not more recognized for his incredible work. Braugher is unlike anything else in modern comedy television.
27. Coral Palms: Part 3
Season 4, Episode 3
The action-packed grand finale of the Coral Palms saga! The squad disobeys CJs (Ken Marino) orders to not go to Florida to help Jake and Holt who are known fugitives, needing to hide out from Figgis and the local cops who don’t believe they too are cops. While Holt impales himself on a pipe and subsequently performs surgery while a horrified Jake averts his gaze, the squad make contact and they set up a trap for Figgis. Jim O’Heir, channeling his inner Jerry Gergich at this moment as the Sheriff, of course, messes up the trap accidentally by forcing Jake to let Figgis go. But as this is the finale, we have to have a big moment and that would be Gina and Terry saving the day by smashing into the fleeing Figgis truck with a semi-trailer. These action-oriented episodes are always few and far between for this comedy, of which Coral Palms Part 3 is one of the best. But the select few are always handled with the same fun energy that you expect of Phil Lord and Christopher Miller who’s visual style was set in the Pilot of the show.
26. Mr. Santiago
Season 4, Episode 7
What I find most interesting about this episode isn’t the main story, despite Jimmy Smits being absolutely perfect as Amy’s scary-but-kind father. No, I’m more intrigued by Adrian Pimento and Captain Holt’s story line of gambling on the Westminster Dog Show. This is some serious attention to character when you realize that Holts obsession over the dog show is just him living his gambling addiction (that will be explored in better detail in a later episode) vicariously through Pimento. In a way it’s a healthy release, but it’s not discussed it just happens. I think it’s just immaculate character and audience development that Andre Braugher is more than capable of layering in to his performance since the very beginning of the show.
25. Halloween III
Season 3, Episode 5
Each Halloween gets better, and each Halloween gets more diverse in who they honor as “detective/genius”. But this seasons episode is all about allowing Amy to be genuinely affected by being outright dismissed from Jake and Holt’s fierce competition. And it’s ‘Halloween III’’s conclusion that opens up these season highlights to great possibilities in future episodes. You don’t typically get to see this type of earnest growth in macho characters and that’s exactly why Brooklyn Nine-Nine is so important and this specific Halloween is such a stand out.
24. Sabotage
Season 2, Episode 19
Now remember when I said earlier that there was a much better Chris Parnell episode of Brooklyn Nine-Nine? Well here it is! Not to spoil the episode, but I hope that wouldn’t matter if you are reading an entire ranking of this series, but Parnell is the man behind setting up Jake on a failed drug test containing cocaine. Parnell is as manic and unhinged as ever, kidnapping Jake and threatening to blackmail and kill him in a decommissioned ice cream truck. The episode is also utterly darling for Terry lifting Gina’s spirits after Holt misses one of her dance performances, and we get a glimpse of what Hitchcock and Scully possibly were like as younger men, effortlessly solving a case, but revealing that they play dumb just so they can continue to be super lazy. I mean, what’s more relatable than that?! Also, as a Texan, I can’t help but love the respectful nod to Senator Wendy Davis with Jake’s blurted out expression of “I stand with Wendy!’
23. Crime and Punishment
Season 4, Episode 22
See! Told Ya! Every season finale has a “____ and _____” title format! In “Crime and Punishment” we flash forward two months to the days before Jake and Rosa are sentenced for Melanie Hawkins bank robbery set-up. They are in a mad dash to find out any information they can that will free the duo, but Hawkins continues to be one step ahead of the Nine-Nine down to the final moments. The episode ends with probably one of the most earnest, bitterly funny moments of the show. As the reality of their guilty verdict washes over Jake, all he can utter is his series-long catchphrase, an increasingly anxious, manic string of “Cool”s. Samberg plays the moment simply, allowing his forthcoming prison time to sink in. It’s one of the strongest endings of the shows run leaving us at a loss of words of how, or if, our heroes are going to make it out of this one.
22. The Bimbo
Season 6, Episode 13
In what world is Captain Raymond Holt just arm candy. I mean sure, he’s a hunk-of-man, but it’s hard to imagine him not being the smartest, most respected guy in the room. But when surrounded by Kevin’s academia peers, that’s exactly where he finds himself. But with the help of Jake, Holt looks to prove his worth to his husbands colleagues by solving an on-campus crime. This is a great episode for Kevin to develop and grow as a character, but I love it because of two incredible moments from Raymond Holt. The first is when he considers the Times Crossword app to be a video game (“Yes, yes—play me my dunce’s tune.” he says, hearing the winning chime of his puzzle), while the second is what Holt says triumphantly when believing he’s found the criminal, “You’ve been caught, Allister! Caught by me. Me and my rock hard brain.” The blending of Braugher droll humor and these silly as fuck lines are exactly why Brooklyn Nine-Nine, six seasons later, can still be as funny as ever.
21. NutriBoom
Season 5, Episode 16
I have a feeling that we will be seeing much more of NutriBoom is Brooklyn Nine-Nine’s sixth season. The cult-like corporation first popped up in ‘HalloVeen’ when Boyle Clone Bill (Winston Story) conned Jake and Charles both into buying into the MLM, or Multi-level marketing, proxy. This is clearly Schur and Goor’s way of tackling the supremely strange rise of these insidious organizations. Add in a mixture of Scientology undertones, and love of celebrity sponsors (NutriBoom’s celeb du jour is Jay Chandrasekhar, one of the geniuses behind Broken Lizard and who’s second career is of directing sitcoms much like Brooklyn Nine-Nine) the possibilities are endless for the stories that the squad could tackle with these nouveau pyramid schemes. The episode is accompanied by following Amy on her first day as sergeant having to navigate working with someone that reminds the squad of herself. It’s a moment to not only highlight the eccentricities she may not see in herself but also to praise the dedication and resourcefulness someone with her neurotic ticks brings to the job.
20. The Big House: Part 2
Season 5, Episode 2
In the second episode of this prison two-parter, Jake agrees to be a snitch for the warden now that he has become part of Romero’s gang. Since Romero controls the influx of all the drugs into the prison, meth renamed Blizz because meth just has bad optics now, he wants Jake to figure out how it’s getting in. While Jake works the case to figure out how he’s smuggling in the Blizz, the Squad are coming up empty handed on pinning Hawkins crimes on her and freeing Jake and Rosa. That is until mafioso Seamus Murphy offers his assistance to Amy, causing ramifications that ripple throughout the rest of season 5. After Hawkins constantly getting away, it’s cathartic for both characters and audience to see her get her comeuppance. But for me, the capper on this episode is Jake’s heartfelt farewell to Caleb, who took a shiv to the stomach to save Jake’s life. As they embrace one final time, Caleb lunges at Jake teeth bared growling like an animal, because lest we forget: though he considers himself more of a woodworker, Caleb is a straight up child munching killer cannibal yo! Give that man his own spin off series stat!
19. Lights Out
Season 7, Episode 13
It’s the return of Sergeant Peanut Butter Not really, but hearing this deep cup Broolyn Nine-Nine character — who has been promoted to Lieutenant much to the chagrin of Boyle – mentioned is a fun throwback for the hardcore fans who’ve been watching since Season One. In the midst of a city wide blackout, Amy goes into labour as Jake is stuck on the streets trying to make his way back to his wife, but he keeps getting held up by people in need (and one hella racist old lady). Meanwhile — and where the episode’s biggest laughs come from – Terry and Holt are trapped in an elevator. Terry suggests he teaches Holt some dance moves to keep the Captain’s mind off of his claustrophobia. Andre Braugher’s commitment to the joke is what elevated this sitcom in the first place, and it’s heartening to see that over seven years later, it’s as fresh as ever.
18. Full Boyle
Season 1, Episode 17
‘Full Boyle’ is a phrase that stays the course of the series, and the genesis of what that term means is as sweet as it is funny. While Charles Boyle toes the line of being inappropriate in his relationships (especially his early pursuits of Rosa), they don’t come across as uncomfortable, because he’s innocently obtuse to anything resembling a normal dating life. Great first date? Charles Boyle says let’s take a tour tomorrow of wine country in Italy! This is the writers sending Boyle’s fantasies into blithe absurdity, so outlandish you can’t help but laugh. While the B plot revolving around wannabe vigilante Super Dan is saved by Nate Torrence’s inherent likeability, it’s the progressive C plot regarding Holt’s organization the ‘African-American Gay and Lesbian New York City Policeman’s Association’ that is what this episode should be remembered for. Holt graciously recognizes that rather than continuing to wield power over an organization he founded, that he allowed his organization to do what he founded it for: open the door of opportunities for other queer people of color on the police force. I believe Holt would agree with the late great Whitney Houston, “I believe the children are our future. Teach them well and let them lead the way!”
17. Kicks
Season 5, Episode 3
Jake’s time in jail had a major, profound impact on his life that has ripple effects throughout season five and I can only imagine for the rest of the life of the show. It’s utterly refreshing to see a cop show deal with a police officer who understands the unique perspective of what life behind bars truly looks like. The show allows him to experience that trauma and gives him the support he needs to say “This is happening, and I need to heal myself before jumping back into full-time work.” When distilled down, it’s quite monumental for any show to tackle this nuanced concept, even more so that it comes from a Nicecore sitcom. We rarely see this type of strength from a male character and let’s be real: I hope more police officers has the mentality that Jake has at this episode’s end. Everyone needs this type of self-awareness, especially our law enforcement.
16. The Honeypot
Season 6, Episode 7
I’ll admit, I had never heard the term “honey pot” before this episode, but I was very much aware of the Jennifer Lawrence vehicle Red Sparrow. That did not mean I knew what Red Sparrow was even about, but after this episode, I know I’ll never forget it. The titular character, played by the always welcome Karan Soni, is sent in as a spy to entice Holt so Commissioner John Kelly can find out who else is opposing his leadership. Between the “sexual chemistry” between Soni and Braugher and the running gag about the eroticism of wooden barrels, this episode is a season six highlight.
15. Ransom
Season 7, Episode 12
As the series continues to try and fill the Gina sized shoes left by Chelsea Peretti, I really hope we see Marc Evan Jackson’s Kevin Cozner move from recurring to regular. As the squad’s two dads, the relationship between Kevin and Holt are a great microcosm of the show: they are funny, weird, sweet characters that are constantly refined and mined for new depths of humor. And nothing’s funnier, or more relatable, than their droll devotion to their dog Cheddar. The episode’s subplots take a backseat to this central mystery, allowing the audience more time to relish in Kevin’s panicked neurosis and Holt going full John Wick for his pooch. Holt’s arc culminates in a lengthy brawl — which feels inspired by They Live — which is the longest serious fight scene I’ve ever seen in a sitcom. The moral of this story? You just don’t fuck with a man’s fluffy boy.
14. Ticking Clocks
Season 6, Episode 14
Nine-Nine has a lot of highs, but no more exciting to me than when they really lean on its action movie aspirations. Sometimes the show really does feel like a fun straight-to-video action movie from the 1990s, and Ticking Clocks is no different. As a hacker closes in on deleting years worth of case files, the squad scours the building looking for their culprit. With great cameos from Sean Astin and Cameron Esposito, this is a brisk episode, featuring the entire ensemble without a single narrative thread feeling like fille. This is one of the finest episodes of Season Six, because it’s working within the confines that made the show such a hit.
13. Ding Dong
Season 7, Episode 7
It’s hard to believe that Kyra Sedgwick, who played Captain Holt’s NYPD foil Madline Wuntch, has been written off the show. We’ll miss their cattiness, the venom in their voices, and the well thought out insults. But while it sucks to lose the character, it did allow for a genuinely moving movement for Raymond Holt as he eulogizes Wuntch at her funeral. He acknowledges that despite their animosity, the relationship was meaningful, and that even when your enemies die, you still must allow yourself to grieve. Even if you once referred to your nemesis as “the devil, and you don’t dance with the devil because you get burned. Also, because in Madeline’s case she has no rhythm, and her hands are like little rat claws.”
12. He Said, She Said
Season 6, Episode 8
One thing I’ve always loved about Brooklyn Nine-Nine is that they approach difficult topics in an honest way while still finding humor surrounding the issues. In this episode, a woman (the always great Briga Heelan) accuses her boss of sexual harassment after she “breaks his penis” rebuffing his advances. The show looks at the issue from multiple angles and thankfully gives Jake the self awareness to take the back seat and listen to the women in his life working through their own past traumas. While these kinds of episodes are few and far between, they still have a steady hand on exploring themes you don’t expect in a Must See TV sitcom.
11. Adrian Pimento
Season 3, Episode 17
I’m not alone in loving Jason Mantzoukas madness, and in Brooklyn Nine-Nine he gets to unleash his inner tortured cop as Adrian Pimento. He’s been through hell, and he kinda loved it, and we kinda love him for loving it. Brooklyn Nine-Nine has always been about eschewing tropes of the cop show, and Mantzoukas is perfect in personifying the dark void they can fall into. Plus, bravo for bringing Pimento and Rosa together in one of the strongest and strangest relationships of the series.
Related Topics: Big List, Brooklyn Nine-Nine, NBC, ranking
