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The 10 Best Captain Holt Episodes of Brooklyn Nine-Nine, Ranked
- Joao Nsita
- 1 hour ago
- 13 min read
You always remember the moment Captain Raymond Holt made you feel something you didn't expect.
Maybe it was a rare flash of emotion breaking through that perfectly composed face. Maybe it was a deadpan line delivered so precisely it took three seconds to register how funny it was. Maybe it was a scene so quietly powerful you had to pause the episode just to sit with it for a moment.
Raymond Holt is one of the greatest TV characters ever written. Full stop. That's not hyperbole — it's the consensus of anyone who has spent real time with this show.
He's a Black, openly gay police captain who navigated decades of systemic prejudice to reach a position of authority — and then used that authority to protect and champion the people around him. He is the funniest, most dignified, most emotionally complex person in every room he enters, and he knows it, and he would never say so. André Braugher brought him to life with a performance so layered that every micro-expression carried the weight of an entire monologue.
Brooklyn Nine-Nine gave us eight seasons of incredible television, but the best Brooklyn Nine-Nine episodes — the ones people still rewatch, quote, and recommend — almost always have one thing in common: Captain Holt at the center of them.
Whether you're a lifelong B99 fan rewatching the whole series for the third time or someone discovering it fresh, these are the Holt episodes you absolutely cannot skip.
These episodes made us laugh, surprised us, moved us, and reminded us why Raymond Holt is more than a fan favorite — he's a television icon.
From witness protection mishaps to interrogation masterclasses, from heartfelt coming-out moments to the series finale that left the whole internet quietly devastated — this list covers the Raymond Holt moments that defined the show and cemented André Braugher's legacy as one of the finest comedic performers of his generation.
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The 10 Best Raymond Holt Episodes in Brooklyn Nine-Nine
10. "The Party" (Season 1, Episode 16)
What it is: The entire squad attends Captain Holt's birthday party and meets his husband Kevin for the first time. What follows is a masterclass in comedy through contrast — a loud, chaotic group of detectives trying desperately to behave themselves inside a perfectly curated, quietly sophisticated home.
Why it works: This is the episode that first revealed who Raymond Holt was beyond the precinct. We get Kevin Cozner — his brilliant, dry, equally reserved husband — and suddenly Holt makes even more sense. Their dynamic is perfect. Two extraordinarily intellectual people who are deeply in love and communicate almost entirely in raised eyebrows and clipped sentences.
The comedic gold here comes from watching the Nine-Nine squad completely fail at being elegant. Amy Santiago studies for the party like it's a final exam. Gina is completely unbothered by the pressure. Jake spills things. It's glorious.
But beneath all the comedy is something genuinely touching — a glimpse into the private life of a man who keeps his personal world very separate from his professional one, and the moment his two worlds awkwardly collide.
This episode is essential viewing for anyone who wants to understand Holt as a full, three-dimensional character — not just the stone-faced captain who keeps his emotions safely locked away.
Tips for rewatching: Pay close attention to every moment Kevin and Holt interact. Their relationship is one of the most underrated love stories in all of TV comedy.
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9. "Moo Moo" (Season 4, Episode 16)
What it is: Terry Jeffords is racially profiled by a fellow NYPD officer while walking in his own neighborhood — off-duty and unarmed — looking for his daughters' toy. When he tries to file a complaint, Holt advises him not to for fear of damaging his career. Terry refuses to stay silent.
Why it works: Brooklyn Nine-Nine rarely shied away from real-world issues, but this episode handles racial profiling with a weight and directness that felt genuinely brave for a network sitcom. There's no easy resolution. There's no tidy lesson wrapped up in 22 minutes. The injustice is shown, it's felt, and it isn't magically fixed.
Holt's role in this episode is particularly compelling. He doesn't give the comfortable answer. He gives the strategic one — and he's both right and wrong. The conversation he has with Terry about navigating systemic racism as a Black man in a predominantly white institution is one of the most honest and painful exchanges the show ever produced.
André Braugher plays Holt's quiet grief over the situation with incredible restraint. You feel everything he's not saying.
This is one of the best Brooklyn Nine-Nine episodes of all time — full stop. Not just for Holt, but for what it says about the world these characters live in.
The episode ends without a tidy resolution — which is part of what makes it so powerful and so rare for a network comedy. Terry files his complaint. Holt supports him. The system is still the system. But the two men have spoken an honest truth to each other, and that honesty matters even when it can't fix everything. That kind of nuance is what separated Brooklyn Nine-Nine from its peers.
Tips for rewatching: Watch this one without distractions. It deserves your full attention.
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8. "Halloween IV" (Season 4, Episode 5)
What it is: The fourth installment of Brooklyn Nine-Nine's legendary Halloween Heist tradition — and the one where Captain Holt reveals he's been playing the long game the whole time.
Why it works: The Halloween Heist episodes are a yearly tradition that became one of the show's most beloved recurring events. But Halloween IV stands apart because it belongs entirely to Holt.
In previous heists, Holt had been a competitor — strategic, sneaky, always underestimated. But this year, he does something nobody sees coming. He engineers a scheme so elaborate, so patient, and so brilliantly cold-blooded that it reframes everything you thought you knew about how he approaches competition.
The reveal is jaw-dropping comedy. The smug satisfaction on Holt's face is immaculate. And the way he delivers his victory speech — with barely a flicker of emotion while the squad loses their minds around him — is peak Raymond Holt.
This episode is pure fun. If you're introducing someone to B99's Captain Holt, this is a great starting point alongside a more emotional episode so they get the full picture.
Tips for rewatching: Rewatch the whole episode looking for the clues you missed the first time around. They're everywhere.
7. "Hitchcock & Scully" (Season 6, Episode 4) / "Holt vs. Wuntch" Arc
What it is: While this episode centers on the origin story of Hitchcock and Scully, the broader Season 6 arc of Holt fighting against his nemesis Deputy Commissioner Madeline Wuntch — who has finally seized enough power to dismantle everything he's built — is essential Holt television.
Why it works: Holt's nemesis relationship with Wuntch (the late, extraordinary Kyra Sedgwick) is one of the funniest ongoing rivalries in modern TV comedy. Their mutual contempt is so specific, so theatrical, and so absurdly petty that it never stops being hilarious.
But the arc isn't just funny — it's revealing. You see how much of Holt's dignity and composure is something he has had to build over a lifetime of fighting people who didn't want him to succeed. His struggle against Wuntch isn't really about professional rivalry. It's about a man who has been underestimated, sidelined, and sabotaged for decades — and who refuses to stop standing his ground.
The Wuntch episodes show Holt at his most venomous, his most petty, his most human, and sometimes his most vulnerable. Every single one is worth your time.
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6. "Ding Dong" (Season 7, Episode 11)
What it is: Madeline Wuntch dies unexpectedly, and Holt is forced to confront his own complicated feelings about the death of his greatest enemy.
Why it works: This is one of the most surprising emotional experiences in the entire series. You expect Holt to celebrate. Instead, you watch him grieve — awkwardly, confusingly, and with a painful honesty that catches you off guard.
Because here's the thing: Holt's rivalry with Wuntch gave him something. An opponent worthy of him. Someone who knew exactly who he was and challenged him at every turn. And when she's gone, there's a strange hollow space left behind.
André Braugher plays this with extraordinary subtlety. The comedy is still there — Holt does attempt to put on a Wuntch death party — but underneath it is something much more real. Grief is complicated. Even for people you hated.
This episode is a perfect example of why Brooklyn Nine-Nine at its best was so much more than a workplace sitcom. It understood people.
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5. "Four Movements" (Season 6, Episode 12)
What it is: Gina Linetti prepares to leave the Nine-Nine, and each of the four movements in this episode centers on a different character saying goodbye. Holt's segment — delivered as a piece of music — is the most unexpectedly beautiful thing the show ever produced.
Why it works: The structure of this episode is creative in the best possible way. Gina's departure is handled with humor and heart. But when it comes time for Holt to say goodbye, the show does something extraordinary.
Rather than a speech or a scene, his farewell is translated into music — because Raymond Holt was classically trained, and because sometimes the most precise man in the room expresses himself best through something beyond words.
It's gorgeous. It's quietly devastating. And it reveals how deeply Holt cares about the people in his squad, even when — especially when — he can't bring himself to say it out loud.
This episode reminds you that one of the great gifts of Brooklyn Nine-Nine was letting Captain Holt be fully, completely human — on his own terms.
4. "Game Night" (Season 5, Episode 10)
What it is: Holt comes out to his mother — and the squad is there for moral support during a game night that goes completely sideways.
Why it works: Here's what makes this episode extraordinary: we already know Holt is gay. He's been out his entire adult life. But coming out to his mother — a woman who has been deeply opposed to his identity — is something he hasn't been able to do.
Watching Raymond Holt, this supremely composed, supremely in-control man, sit across from his mother and tell her the truth about himself is one of the most moving moments in the entire series. He's scared. It shows. And André Braugher earns every second of it.
The squad hovering in the background — nervous, protective, desperately trying to give him space while also being clearly ready to step in if needed — is both hilarious and genuinely touching.
This is what Brooklyn Nine-Nine did better than almost any other show: it made you feel something real within a comedy, without breaking the tone.
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3. "9 Days" (Season 3, Episode 12)
What it is: Jake and Holt are both exposed to mumps and quarantined together in Holt's home for nine days. Neither man is particularly good at being vulnerable or idle. Chaos, bonding, and genuine emotional growth follow.
Why it works: This episode is a masterpiece of character-based comedy. Jake and Holt are stuck together with nothing to do but talk, bicker, and inadvertently learn about each other — and what emerges is one of the great mentor-mentee TV friendships.
Holt can't stop solving puzzles. Jake can't stop being annoying. But over the course of those nine days, you watch them drop their professional personas and just be people together. It's funny and warm and a little heartbreaking in the best possible way.
The episode also gives us one of Holt's great hidden qualities: his unexpected competitive streak when it comes to completely meaningless things. The crossword puzzle competition alone is worth the entire runtime.
This is peak Jake-Holt dynamic. If you love their relationship, this episode is non-negotiable.
2. "Coral Palms" Trilogy (Season 4, Episodes 1–3)
What it is: After their lives are threatened by mob boss Jimmy Figgis, Jake and Holt are placed in the Witness Protection Program and relocated to Florida — a state that is basically Holt's personal version of purgatory.
Why it works: Three full episodes of Jake Peralta and Raymond Holt playing small-town Florida residents is exactly as funny as you'd expect — and somehow even better.
Holt becomes Kyle, an assistant manager at a fun zone. Jake becomes Larry, a man with frosted tips. Neither of them is remotely equipped for this new life, but Holt's inability to stop being Holt — precise, formal, relentlessly dignified — in an environment that is aggressively casual makes for non-stop comedy.
But the trilogy also works because the stakes are real. These two people, who have developed a genuinely deep bond over three seasons, are now completely isolated from the only world they know — and they only have each other.
The way their friendship deepens during these episodes, through ridiculous circumstances and genuine danger, is one of the most satisfying arcs in the entire series.
This is Brooklyn Nine-Nine at its best. Watch this trilogy in one sitting if you can.
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1. "The Box" (Season 5, Episode 14)
What it is: Jake and Holt spend the night interrogating a murder suspect — a dentist named Phillip Davidson, played by Sterling K. Brown — in a nearly bottle-episode format that is, without question, the finest hour of Brooklyn Nine-Nine.
Why it works: This episode is the answer to anyone who ever dismissed Brooklyn Nine-Nine as "just a comedy." Because "The Box" is genuinely brilliant television, full stop.
Phillip Davidson is an intelligent, self-satisfied murderer who knows exactly what he's doing. Jake and Holt are two detectives who know he did it — but can't prove it. What follows is a two-against-one chess match across 22 minutes that never loses tension, never stops being clever, and never stops being deeply, satisfyingly character-revealing.
Here's what "The Box" does that makes it transcendent: it shows you who Jake Peralta and Raymond Holt actually are when all the humor is stripped away. Jake's instincts. Holt's precision. Their trust in each other. Their willingness to switch tactics, defer to one another, and push forward together.
The guest performance by Sterling K. Brown is extraordinary — genuinely menacing without ever being cartoonish. And the final reveal, the way the trap closes, is one of the most satisfying moments in the entire show.
This is the best Raymond Holt episode. And it's one of the best episodes of any TV show in the last decade.
Watch it immediately. Then watch it again.
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Conclusion
Raymond Holt isn't just one of the best characters in Brooklyn Nine-Nine. He's one of the best characters in the history of television comedy.
What made him extraordinary wasn't just the humor — though the humor was exceptional. It was the fact that he was written and performed as a fully realized human being. A man who had fought his entire career for basic dignity and respect. A man who loved deeply but expressed it in ways most people couldn't read. A man who was simultaneously the funniest person in the room and the most emotionally complex.
André Braugher gave everything to this role, and the show gave him the material worthy of that talent.
If you're rewatching Brooklyn Nine-Nine, let these episodes be your guide. And if you haven't started yet — you're in for something special.
These are the episodes that reminded us why we love television.
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FAQs: The Best Raymond Holt Episodes in Brooklyn Nine-Nine
1. What is the best Raymond Holt episode in Brooklyn Nine-Nine? Most fans and critics agree that "The Box" (Season 5, Episode 14) is the best Holt episode in the series. It's a near-bottle episode featuring a gripping interrogation with Sterling K. Brown and showcases both Holt's intelligence and his deep bond with Jake Peralta.
2. What season is Raymond Holt at his best? Holt shines across all eight seasons, but Seasons 4 and 5 are particularly strong for his character — featuring the Coral Palms trilogy, "The Box," "Game Night," and "Moo Moo," all of which are widely considered among the show's finest hours.
3. Which episode shows Captain Holt's emotional side? "Game Night" (Season 5, Episode 10), where Holt comes out to his mother, is widely regarded as the most emotionally vulnerable Holt episode. "Ding Dong" and "Four Movements" also offer unexpected emotional depth.
4. Is "The Box" the best Brooklyn Nine-Nine episode overall? Many fans and critics consider "The Box" not only the best Holt episode but the single best episode of Brooklyn Nine-Nine period. Its tightly written script, excellent guest performance, and perfect showcase of the Jake-Holt dynamic make it near-flawless.
5. What are the funniest Captain Holt episodes? The Coral Palms trilogy (Season 4, Episodes 1–3), "9 Days" (Season 3), and the Halloween Heist episodes — especially "Halloween IV" — are among the funniest Holt-centric episodes.
6. What is the Coral Palms episode about? "Coral Palms" refers to a three-episode arc (Season 4, Episodes 1–3) where Jake and Holt are placed in the Witness Protection Program in Florida after their lives are threatened. It's hilarious, character-rich, and deeply rewarding.
7. Who plays Captain Holt in Brooklyn Nine-Nine? Captain Raymond Holt is played by the late André Braugher, a two-time Emmy Award-winning actor whose performance is widely considered one of the greatest in TV comedy history.
8. Does Captain Holt ever cry or show emotion? Holt rarely shows overt emotion, but the show gives him several deeply moving moments — including "Game Night," "Four Movements," "Ding Dong," and the series finale. When Holt does crack, it lands with enormous impact precisely because it's so rare.
9. What episode does Holt say "hot damn"? Holt's legendary "Hot Damn!" moment occurs in Season 2, Episode 3 ("Jake and Sophia"), during a cold open where the squad bets on why Amy Santiago is running late. When his guess turns out to be correct, Holt loses control for one glorious second. It became one of the most quoted lines in the show.
10. Is Brooklyn Nine-Nine worth watching just for Captain Holt? Absolutely — and then some. Captain Holt is one of the greatest reasons to watch Brooklyn Nine-Nine, but the full ensemble, the writing quality, and the show's heart make it one of the best TV comedies of the 2010s. Holt is the crown jewel, but the whole show is gold.
External resource: NBC's official ranking of Captain Holt's best episodes
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