Top 10 Hilarious Holt Moments from Brooklyn Nine-Nine

All hail the captain. Welcome to WatchMojo and today we're counting down our picks for the Top 10 Hilarious Holt Moments from Brooklyn Nine-Nine.

For this list we're looking at the funniest lines and scenes from Captain Raymond Holt. We're basing our choices on a mix of hilarious dialogue and everything that makes Holt so endearing. This covers multiple seasons of the show, so a SPOILER ALERT is in order.

#10: Kwazy Cupcakes
"Tactical Village" (2014)

Captain Holt has never been one to engage with pop culture, so it was particularly surprising when he started playing the mobile game Kwazy Cupcakes. Though he tried to hide his addiction at first, it was hilarious watching him painfully delete the app. The Captain really gets out of character with his bathroom gaming sessions and real-life color-matching too. Holt even broke his use of proper grammar to name the app, which got exceptionally ridiculous when he tried to angrily defend his behavior. Since the Captain initially mocked Gina's obsession with Kwazy Cupcakes, it was priceless to see him become far worse than her.

#9: DE DE DE DEREK
"Coral Palms: Part 1" (2016)

In this episode, a vicious mobster forces Jake and Holt into witness protection, prompting the Captain to hide important case files from Jake to keep them both safe. Given how badly Jake wants to solve the case and go home, he punishes Holt's decision by forcing him to DJ. The Captain's rapping is hysterically wholesome, and it's surreal to see him be so musical. But his funky breakdown is so dead-pan that it's nearly impossible not to laugh. Holt loves a dance-off, (xref) and we get to see more of his zany moves here. Plus watching him take out his anger through a birthday rap is comically petty.

#8: Yas Queen
"The Big House: Part 1"

While Rosa is in prison, Holt and Terry fight over who will do her chores and more importantly… ride her motorcycle. Terry is scared of injuring himself on the bike, so he tries using his kids to excuse himself from danger. Rather than folding however, the Captain cheekily uses his sexuality to gain the upper hand. This comeback is all the more satisfying thanks to Holt's numerous stories about struggling as a gay officer. But it's the Captain's hilarious shut-down to Terry that leaves us in stitches. From the snap to his expressionless face, this is Holt at his witty best.

#7: VELVET THUNDER
"The Chopper" (2015)

Jake is so excited about getting full support for his case that he gives all his coworkers wacky codenames. While Holt is reluctant about all the colorful titles at first, he amusingly embraces all of Jake's ideas once they’ve solved the crime. Though his call to the helicopter is exciting, it's side-splitting to see the Captain remembers everyone's codenames too. Holt also picks his own outrageous name, and delivers it to Jake with an absurdly bass-filled and aggressive voice. As a complete turnaround and eccentric break in character, the Captain's switch to an action hero is unforgettably funny.

#6: Podium Prank
"Sicko" (2019)

Holt's sense of humor is a hard one to pin down, but Jake tries to prank one of his meetings anyway. After everyone shoots his ideas down however, Jake angrily decides to just slightly nudge the Captain's podium. Despite the virtually insignificant move, Holt is utterly baffled, giving Jake a far better reaction than he ever could have reasonably hoped for. It's difficult not to laugh along as the Captain goes into a ludicrous fit of giggles and smiles. Holt's over-the-top reaction also cleverly takes his fixation on details to a surreal new level. Nevertheless, hearing him question his own officers about the gag shows he still doesn't totally understand pranks himself.

#5: Going Into Witness Protection
"Coral Palms: Part 1" & "Coral Palms: Part 2" (2016)

Witness protection means Jake and Holt need new identities, so the Captain becomes a straight guy named Greg. Raymond's gossip with his speed-walking group is hilariously out of character, and sometimes bizarrely mean. However, Holt's heterosexual persona is all the more entertaining because of how explicitly he talks about his sex life and women. He also cleverly mocks this attitude as part of the straight lifestyle. And though his comments on thigh-gaps are pretty rich too (xref), the Captain's fixation on breasts is way funnier. Given how professional and nonsexual Holt usually is, this change of tone is priceless to watch.

#4: Vindication!
"Monster in the Closet" (2016)

To prepare for Rosa's wedding at a bar, Holt is tasked with making a balloon arch. However the Captain gets a little carried away and treats his arts and crafts chore like it's a piece of art. Raymond's poetic description of arches and balloons is wonderfully silly, though hearing him graphically talk about creating his sculpture is comedic with a touch of “ew”. With this passion for art, it's genuinely laughable that Holt tries to hide his arch from Rosa when the wedding is called off. It's her praise on the other hand that gives us a rare moment of Raymond at his proudest and most hysterically loud.

#3: Dissing Wuntch
Multiple Episodes

Captain Holt and Madeline Wuntch have a bitter rivalry, and they never miss an opportunity to rip into each other. Whether it's comparing her to the devil, animals or death itself, Raymond gets comically mean when Wuntch shows up. But what keeps us laughing at this recurring bit is how often Holt uses Madeline's comebacks against her. In fact the blunt way he talks about her age is so dry that it leaves us in stitches. Even in later seasons, he'll hilariously call her a witch just to show off. With the clear joy and excitement that the Captain gets from insulting Wuntch, their feud is a comedic goldmine.

#2: Bone!?!
"Skyfire Cycle" (2016)

A series of night shifts puts tension on Raymond's marriage, which causes him and husband Kevin to start fighting over a math problem. But when Rosa insists they just need some intimate time together, Holt doesn't exactly respond well to the suggestion. His outburst is unusually angry, and his loud yelling is too over-the-top not to laugh at. Plus the way the Captain shakes his whole body while bracing himself against a door frame is unbelievably wacky. The fact that he gets defensive enough about his home-life to rant for 40 minutes is funny, but it’s the intensity of this overreaction to such a minor offense that really keeps us laughing.

Before we get to our top pick, here are a few honorable mentions:

Captures the Disco Strangler
"He Said, She Said" (2019)

Street Meat
"Windbreaker City" (2015)

Hula Hooping Accident
“Unsolvable” (2014)

You're Just a Common Bitch!
"HalloVeen" (2017)

Secret Handshakes
“The Bimbo” (2019)

#1: Hot Damn!
"Jake and Sophia" (2014)

When the officers of the Nine-Nine aren’t working one morning, Captain Holt can’t help but be upset with them. As soon as he hears they’re taking bets on Amy Santiago's tardy behavior however, he does a hilarious and unexpected 180, comically joining in. Though the Captain's theory seems mundane at first, it’s refreshing to see him finally get playful with his coworkers. He even hysterically abuses his power to make Amy talk. But it’s Holt's ecstatic reaction to winning the bet that truly gets us cracking up. Given how rarely Raymond would cut loose at this point in the show, 'Hot Damn!' became arguably his funniest moment and one of the series most memorable opens.