Content Warning: This article contains references/discussions to racism, sexual assault, and homophobia
The genius of Brooklyn Nine-Nine lies in its ability to elicit a kaleidoscope of emotions from its viewers, and this is primarily down to its cast of well-written and relatable characters. Brooklyn Nine-Nine is mainly associated with being one of the funniest sitcoms ever, and while the show is hilarious for the majority of the time, there are many moments of great poignancy and sadness.
The saddest quotes are often found during these more serious moments, and the impact of the lines is often augmented by the actors’ brilliant delivery of them. Throughout Brooklyn Nine-Nine’s eight seasons, the cast of characters has become like a second family for many fans, so seeing them speak at such low moments is bound to get the tears flowing.
Charles Boyle To Rosa Diaz (Season 3, Episode 12)
“I’m Sad, Jason Died This Morning.”
Boyle is distraught at the beginning of season 3’s “9 Days” due to the loss of his dog, Jason. Although Rosa does not accept Boyle’s sorrow at first, she later understands after getting a dog of her own. All pet owners understand that Boyle sitting curled up in a ball under his desk and wearing all black is not an overaction to the death of Jason as they had seen how much he adored his pets.
After Rosa asks Boyle what is wrong, he delivers one of the saddest lines in the series, made sadder by Joe Lo Truglio’s excellent acting. Boyle is understandably choked up about the loss of his dog, and this is captured excellently in this quote.
Jake Peralta To Charles Boyle (Season 4, Episode 15)
“Every Case With You Is The Best Case Ever.”
With the fate of the Nine-Nine resting on their shoulders in “The Last Ride,” Jake and Boyle must make a huge drug bust to save the precinct. However, in an admirable act of selflessness, they decide not to make the bust and stake the dealers out instead so that they can catch a bigger fish.
Having made the decision not to save the precinct, Jake and Boyle have a very sad conversation about the squad being split up and moved to different precincts, which results in both of them tearing up and Jake expresses this quote to Charles. Considering how it’s usually Boyle who gets sentimental about their friendship, it really touched fans to hear that their relationship wasn’t one-sided. Jake and Boyle had shared many iconic Brooklyn Nine-Nine moments so to see them potentially torn apart was heartbreaking.
Rosa Diaz To Raymond Holt (Season 3, Episode 6)
“What If I Never Get A Second Chance.”
Break-ups are never easy, and even somebody as tough as Rosa feels her fair share of heartache. Having just broken up with Marcus, Rosa is worried that she will never find love again and is uncharacteristically reduced to tears. Her tearfulness spreads to Captain Holt, who also uncharacteristically begins to cry.
The whole scene is very sad, and the sadness is magnified by the fact that Rosa and Holt, who are usually the strongest characters in Brooklyn Nine-Nine, look so very vulnerable. A weeping Rosa delivers the tragic line to Holt, who “acknowledges” her feelings in a beautifully comforting way.
Rosa Diaz To Her Parents (Season 5, Episode 10)
“So You Would Rather Me Be Some Dude’s Mistress, Than Be In A Loving Relationship With A Woman?”
Rosa admitted in the early seasons of Brooklyn Nine-Nine that she was not very close with her family, or anybody for that matter; she was quite the enigma. However, as the series went on and Rosa’s character developed, she grew closer with her parents, mainly thanks to her time spent away from them in prison.
Rosa’s newfound closeness with her parents is what makes the events of “Game Night” so sad and the quote even sadder. After telling her parents that she is bisexual, they respond poorly, to say the least, leaving Rosa devasted and in genuine disbelief. Seeing Rosa so distraught is not only heartbreaking but the fact that she had been trying really hard to bond with them and they weren’t giving her the same love and respect back was deeply upsetting too.
Amy Santiago To Jake Peralta (Season 6, Episode 8)
“He Said That He Felt Like He Deserved Something In Return For My Career.”
“He Said, She Said” is one of the more serious episodes in Brooklyn Nine-Nine that discussed some very sensitive and relevant subject matter in a respectful way. It is no surprise then that the episode contains one of the saddest quotes in the series.
After having no luck in solving a sexual assault case, Amy is distraught. She opens up to Jake about why the case is of particular importance to her, which leads to a very heartbreaking quote detailing how she had been the recipient of inappropriate sexual advances. Seeing Amy so upset while telling Jake about what happened to her really adds to the sadness of the quote.
Captain Holt To Amy Santiago (Season 8, Episode 1)
“It’s Been A Tough Year To Be A Black Man, And A Police Captain, And A Human.”
Before season 8, Kevin and Holt are arguably the strongest couple in Brooklyn Nine-Nine. However, at the beginning of season 8, it is revealed that they have split up, which is devastating news for fans and even more devastating for Captain Holt. Amy notices his sadness and asks if everything is okay with him, leading to a very sad conversation and one of the saddest quotes in the series.
Holt explains how difficult things have been for him in particular, which he says with a heavy heart and a tear in his eye. Andre Braugher delivers the line with such power and emotional evocation that it is impossible not the be saddened by it, especially considering the context in which it was said.
Jake Peralta To Roger Peralta (Season 2, Episode 18)
“I’ve Been Making Excuses For You My Whole Life, But You’re A Pretty Crappy Father, And Until You’re Ready To Be A Good One, Don’t Call Me.”
Jake’s issues with his father are not very well hidden and are often used as a comedic device throughout the show. However, the reality of Jake and his father’s relationship is quite tragic in the earlier seasons and is actually quite a sad situation.
This is summed up by the quote in “Captain Peralta,” where Jake finally confronts his father about being a bad parent. It is a moment of great triumph for Jake, but one cannot help but feel saddened by what he says to his father. In later seasons, the Peralta men make amends, but the journey is certainly not a pleasant one for either of them.
Terry Jeffords (Season 4, Episode 16)
“I Was A Black Man, A Dangerous Black Man. That’s All He Could See: A Threat.”
In “Moo Moo,” Terry is stopped and harassed by a police officer simply because he was a Black man. Understandably, he is outraged by this and seeks justice for the incident. Terry is shocked and saddened by the lack of remorse that the offending officer shows and asks Captain Holt for further advice on how to pursue justice.
What happened to Terry is extremely upsetting in and of itself, but his conversation with Captain Holt later in the episode is even sadder. Terry explains how vulnerable and alienated he felt during the incident, and the pain in his voice while speaking makes the quote one of the saddest in the series.
Captain Holt To The Precinct (Season 2, Episode 23)
“These Have Been The Best Years Of My Career… And I Know That Every One Of You Gave Me Everything You Had, And I Will Never Forget It.”
In the season 2 finale, Wuntch maliciously gives Holt a “promotion” which means that he must leave the Nine-Nine. He reveals this to the squad at the end of the episode, which devastates everybody and creates a very sad atmosphere in the precinct.
In the early seasons of Brooklyn Nine-Nine, Holt is not very emotive and is generally composed and serious. However, when delivering his final speech to the squad, Holt is holding back the tears, which makes the situation and the quote so much heartbreaking. The despondent feeling among the squad during the announcement transcends the screen and can genuinely be felt by fans of the show.
Jake Peralta To The Precinct & Fans (Season 8, Episode 10)
“Well, I Guess This Is It. So Long Nine-Nine”
They are the words that no Brooklyn Nine-Nine fans ever wanted to hear, the final words spoken in the show that bid goodbye to the ninety-ninth precinct. It is only fitting that Jake delivers the final line of the show, and Andy Samberg does so with aplomb evoking great poignancy.
True fans of Brooklyn Nine-Nine will always be close to tears as these words are uttered, as they punctuate an amazing eight-season journey that millions have enjoyed. While everything must come to an end at some point, it is always sad when a show as wonderful as Brooklyn Nine-Nine ceases production, and Jake’s final line captures this sentiment.
