Aside from perhaps Jake Peralta, Captain Raymond Holt is arguably one of the funniest characters in Brooklyn Nine-Nine despite him not being a fun person in the slightest. In fact, he actually hates the word.

Captain Holt commands respect with his general demeanor but also due to how he rose through the ranks to where he is now, as an openly gay Black officer. Despite this, he is a stickler for the rules, and his brain will often not process situations the way human beings would normally approach them. The authoritative voice of Andre Braugher portrayed the character perfectly, and several quotes end up being hilarious due to the context, delivery, and general meaning of the words he says.

Updated by Mayra Garcia on December 14, 2023: On December 12, 2023, it was announced that actor Andre Braugher sadly passed away on December 11. The actor, famously known for his role as Captain Raymond Holt, will be thoroughly missed by Brooklyn Nine-Nine's fans. Braugher's performance as Holt became a staple in Black and LGBTQ+ representation, and his deadpan delivery brought joy to thousands. These hilarious Captain Holt quotes are only a taste of Braugher's legacy in television.

10 "You've Helped Me Find My Smile."

You've helped me find my smile.

Captain Holt is well known for his hilariously monotoned delivery, with very little facial expression, especially in the first few seasons of Brooklyn Nine-Nine. In the opening episode of the second season, "Undercover," Captain Holt opens up to Terry about the stress that he has been under recently, noting that his husband, Kevin, is concerned that he is no longer smiling.

The delivery of this whole interaction was in Holt's classic one-toned voice. This made for a hilarious interaction when Terry sat opposite him and could not see any change in facial expression whatsoever.

9 "...I've Never Been Happier."

I went to Barbados with my husband. We wove hats out of palm fronds and swam with the stingrays. I’ve never been happier.

Another example of Andre Braugher's incredible delivery as Captain Holt comes when the squad is trying to figure out what sort of mood the Captain is in. Each team member recalls times that he has said things both delightfully happy and heartbreakingly sad, all with the same tone of voice.

In this particular example, Rosa sees the Captain looking down and asks him if he is okay. The Captain replies and says how amazing his holiday was, while a baffled Rosa looks on, both confused and incredibly uncomfortable.

8 "...Is This a Police Precinct or a Turkish Bazaar?"

Coat, coat, jacket, coat. Is this a police precinct or a Turkish bazaar?

In "The Wednesday Incident," Jake is determined to prove that he isn't the cause of Captain Holt's bad mood despite inadvertently flooding his office by opening a bottle of cider and setting the sprinklers off. Jake claims Holt was already angry before this due to anger regarding all the coats and jackets in the break room.

The delivery of this quote is what makes it so good once again, with Holt actually displaying signs of anger in his words instead of the usual linear and monotonic delivery. These rare moments always added something to his scenes, making Brooklyn Nine-Nine one of the best sitcoms ever.

7 "Hot Damn!"

Hot damn!

When Captain Holt lets loose, it lights up the entire room, as it is both surprising and completely out of character. When the squad is trying to guess the reason why Amy is late for work, the Captain joins in and finds it fun. When his prediction turns out to be correct, he celebrates out of the blue with "Hot damn!"

In a much later episode, Jake and Holt are trying to get a confession out of a dentist who pulled off the perfect crime. Jake finally manages to get the confession, which leaves Holt bewildered and shocked, with him shouting "Oh damn" three times.

6 "I Did Mean Woke, but It Is Grammatically Incoherent."

I did mean "woke," but it is grammatically incoherent.

When Rosa announces to the squad that she is bisexual, Captain Holt comments on how the Nine-Nine is receiving the news much better than when he came out to his colleagues, saying that they were not "as the kids say, awake." By the end of the episode, he actually has a beautiful heart-to-heart with Rosa, but before, the "woke" joke is perfect to defuse any tension.

Captain Holt is a stickler for accurate grammar, so for him to say something so topically relevant while not stooping to using the actual grammar intended for the use of the word is classic Holt. This is one of many instances of Holt saying contextually correct things but ringing alarm bells for everyone else in the conversation, as it doesn't make complete sense.

5 "You Took the Wrong Fluffy Boy!"

“You took the wrong fluffy boy!”

By the seventh season of Brooklyn Nine-Nine, Captain Holt openly expresses his emotions more often. When Holt and Kevin's beloved dog, Cheddar, goes missing and turns out to have been kidnapped, Holt and Kevin are in disarray.

Holt keeps repeating the same words, "They took our fluffy boy," and then when he finally apprehends the criminal who took Cheddar in the first place, he shouts, "You took the wrong fluffy boy." His passion and anger at the thought of his dog being hurt in any way is a refreshing new look at his character, as he is all emotion and sheer desperation.

4 "Why Would You Intentionally Spill Beans?..."

Why would you intentionally spill beans? They're one of nature's most densely packed protein sources, and they remain unsullied by flavor.

There are countless situations where Captain Holt will misunderstand or purposely pick apart phrases or words that are either too modern for him or just don't make logical sense. On one occasion, when Gina says the phrase "spill the beans" in a sentence, Holt has obviously not heard this applied in a sentence before and doesn't understand the context.

Jake's running joke that Captain Holt is a robot is only fueled and helped by Holt saying things like this. No one else but Hold would say things like this, especially about mundane phrases used in everyday language.

3 "...Call Me Velvet Thunder."

No, from now on, call me Velvet Thunder.

When Captain Holt is under pressure from Wuntch, he insists on joining Jake and Charles with their case, mainly to keep an eye on Jake and ensure that he doesn't do anything to get the Nine-Nine in even more trouble. Jake begins to nag Holt about wanting and needing a chopper for the case, and when he finally gets his way, he gives an angry Captain Holt the nickname "Wet Blanket."

However, when they make a breakthrough with the case, Holt finds his enthusiasm once again, and to Jake's delight, he suggests that they take the chopper, and he changes his name to "Velvet Thunder." The delivery of this line is perfection from Andre Braugher, with him pausing between velvet and thunder for extra emphasis.

2 "...Bloop, There It Is."

Oh, I’ve caused a problem. I think I am getting a text message. Bloop, there it is.

The problem with Captain Holt being on a different planet in terms of how he interacts socially is that he can inadvertently say things he shouldn't or act in a way that may be perceived as rude. The awkwardness of these interactions is what makes Brooklyn Nine-Nine such a funny series.

Captain Holt accidentally lets slip to Terry's wife, Sharon, about Terry being cleared for field duty once again and leaping in to subdue a gunman while he keeps digging a hole for himself by making it worse. After the initial interaction, Holt doesn't realize that Terry has been lying until it is too late, and the awkwardness has reached its peak. He tries to defuse the awkwardness, but it just gets worse from there.

1 "...Who's Guarding Hades?"

Captain Wuntch, good to see you. But if you’re here, who's guarding Hades?

Holt and Wuntch used to have a good relationship as colleagues, but over the years, this would sour and turn into a rivalry full of jests and taunts. Seeing Wuntch sparks the creative side of Captain Holt, and he composes some truly hilarious, witty insults and remarks toward Wuntch.

If anything, Holt's relationship with Wuntch allows him to creatively let out some steam and anger in a fun way. Holt's insults and Wuntch's schemes and retorts bounce right off of each other and make for some terrific interactions. This quote is one of the most iconic insults toward Wuntch, showcasing his knowledge of Greek mythology, so it's one of Raymond Holt's best quotes ever.