10 Best Raymond Holt moments from Brooklyn 99

Captain Raymond Holt isn't merely the Nine-Nine's commanding officer: he is one of the most iconic characters of modern sitcom history. Portrayed brilliantly by Andre Braugher, Holt's deadpan delivery, impeccable wit, and sudden bursts of bizarre behavior make him an inexhaustible fountain of comedy. Unlike his TV counterparts, Captain Holt balances a strict professional demeanor with an endearing oddball attitude and, therefore, significantly mixes warmth with moments of utter absurdity.

What makes Raymond Holt unbelievably funny is his unshakeable seriousness while doing something hilariously ridiculous. Whether he is declaring victory over a dog bone, misusing slang with robotic precision an expression on the countenance of few, or breaking into a rare fit of giggles, the man knows how to time his jokes to perfection. More than plain amusement, Holt stands for strength, representation, and integrity: three characteristics that make any character quite dear.

From classic insults to the endless adoration of Cheddar the corgi, Raymond Holt has brought us some of Brooklyn Nine-Nine's funniest moments. Right now, let's take a look at his ten - yes, ten! - best scenes, each one proving why he remains a fan favorite.

1) Raymond Holt’s Unexpected Outburst of Excitement

Raymond Holt is so well known for his unshakeable calm that his scream of “Hot damn!” at this moment is notably funny. This was during the precinct’s third annual Halloween Heist when Holt realized that he’d been outwitted. The rare moment of emotion from Holt is shocking for everyone in the precinct, especially for Jake Peralta, who lives for moments like this. It became an instant favorite among fans, inspiring endless memes and GIFs. What makes it funny is how Holt goes back to his deadpan look, which says, 'Okay, that was fun,' in less than a second.

2) A Victorious Shout That Became Legendary

Every Halloween Heist was serious business for Holt, but in Season 5, he finally wins and deserves it. He calls himself the Grand Champion of the Nine-Nine, bellowing, "BONE!" at the top of his lungs while lifting a literal dog bone over his head. Absurd, yet fitting; it shows that beneath all that seriousness, Raymond Holt enjoys the game just as much as Jake does. This moment became one of Brooklyn Nine-Nine's most hilarious, and fans across the globe turned "BONE!" into a catchphrase.

3) The Most Awkward Attempt at Slang

Raymond Holt seldom breaks his sophisticated vocabulary, which is why his attempt to imitate Jake's slang has him saying how "Noice smort" in a robotic tone, and leaves the audience rolling. This is seen when he acknowledges Rosa and Jake's clever plan during yet another Halloween Heist. The meat of the joke comes from Holt's stiff delivery like he was trying out the emotions of a human for the first time. The awfulness of the experience is increased because, while trying to fit in, his awkwardness does not falter.

4) Holt’s Secret Addiction to Mobile Games

Captain Holt-preferably quietly laughing to himself over a mobile game such as "Kwazy Kupcakes" is richly funny. But it is Holt's descent into uncontrolled giggles that cements this scene's legendary status. As Captain Holt comes around to the game despite his derisive comments and gets quite addicted to it, Peralta discovers him playing and Holt tries desperately to contain a laugh but utterly fails. His low, restrained chuckle is something we have never seen before. It was one brief insight into the funny side of Raymond Holt, reinforcing the concept that even the most serious people have a soft side for guilty pleasures.

5) The Most Dramatic Celebration Over Yogurt

Holt accuses Terry of scarfing down his precious yogurt, but, of course, Terry denies it. Holt did not believe him. Later on, of course, Holt bursts into the precinct and shouts "Vindication!" after Terry is caught red-handed on security footage, a classic "gotcha" moment; it was one of Raymond Holt's biggest dramatic reactions, made much funnier by his apparent delight in being right about it. And of course, the fact that Holt carries a grudge over food is something one can relate to, which made this moment an unexpected fan favorite. It is perfectly delivered, found somewhere between stoicism and a rare outburst of joy.

6) The Perfectly Delivered Farewell Roast

Holt is the king of savage one-liners, but his insult to Gina in Season 6 is one of his best. When Gina bellows that she is leaving the precinct, Holt simply says, "You're overdoing it." The best part is that Gina, the drama queen, does not seem to be affected. For all of Holt's supposed lack of humor, he delivers this line with pitch-perfect deadpan. Such delivery amounts to a master class in comic timing, proving that Raymond Holt doesn't need the loudest voice to make his point. It is by such measures a great example of how Brooklyn Nine-Nine expertly balanced emotional farewells with pure comedic gold.

7) The Hilarious Confession That Shocked Jake

Raymond Holt's Gaffes Reach a Whole New Level as He proclaims Himself a Pineapple Slut describing his love for pineapples. The word pulls Jake off in an unexpected direction and becomes one of the greatest reaction shots of the entire series. The moment is classic Holt: completely unaware of how absurd his words sound but saying them with total conviction. This scene was immediately embraced by fans, turning the term "Pineapple Slut" into a running gag within the Brooklyn Nine-Nine fanbase. It's a great reminder that Holt can bask in some of the most outrageous moments of the series despite being a very correct and serious leader.

8) When Holt Finally Lost His Cool

Raymond Holt normally remains the voice of reason, but with his longtime rival, Commissioner Kelly, spoiling the game, he finally snaps. Frustrated to the point of shouting, "I am losing my COOOO COOOO!" in an exaggerated voice, shocking the squad, he reduces the drama to a mere melodramatic sanity breakdown. It is a rare show of emotion contrasting with his standard no-chil-out delivery. The absurdity of the moment had audiences in complete hysterics as Holt's frustration had been building up for seasons on end. Seeing him finally lose his cool is not only comedic gold but a reminder that even the most composed people have their breaking point.

9) The Ultimate Dance Showdown With His Rival

The rivalry between Raymond Holt and Madeline Wuntch is storied, but the dance-off that broke out between them is undoubtedly one of their most hilarious moments. At an event where Wuntch attempts to humiliate him, Holt surprises everyone by pouring it on with some unexpected, terrific moves. It's funny because he doesn't merely dance; he annihilates her in a robotic showdown. It's one of the few times he gives himself over to the absurdity of a given situation, and fans adored every moment of it- dancing his way to victory over Wuntch despite their bitter rivalry.

10) Holt’s Unbreakable Bond With His Corgi

Raymond Holt's bond with his corgi Cheddar comes out as one of the most wholesome or delightful things in Brooklyn Nine-Nine. From calling him a "brave little soldier," to masterminding elaborate dog heists, and even engaging in police operations with the corgi, Holt's devotion to Cheddar knows no bounds. One of the best moments is when Holt comes pretty close to admitting that Cheddar has gotten fat, saying, "He's gotten fat," in a heartbroken tone. It's such a small moment, but it speaks volumes about Holt's love for his dog. He treats Cheddar like a commanding officer, ridiculously so, but it shows how deep Holt's love runs.