When Brooklyn Nine-Nine first aired, Captain Raymond Holt won over the hearts of fans with his humor. As many fans know, Holt's sense of humor is a bit dry. Sometimes fans can't even tell if he's joking or not. However, that's not to say his humor hasn't failed in rousing a hearty laugh from audiences.

RELATED: 15 Best Captain Holt Quotes From Brooklyn Nine-Nine

Especially when in regards to his arch-nemesis, Madeline Wuntch. When it comes to the Commissioner, Holt doesn't hold back with the insults. Holt has effectively "roasted"  Wuntch various times with insults so clever, he leaves fans crying with laughter hours later. As Holt once said, they were "star-crossed haters."

"So Much Time With Your Ear To The Pavement, It's a Pity A Truck Hasn't Run Over Your Head." (2.05)

Wuntch in season 2 episode 5 of Brooklyn Nine-Nine

In season two, episode five of the show, the squad has to deal with Internal Affairs. Convinced there's a mole in the department, Jake and Captain Holt search for clues who it might be. Along the way, Holt gets a visit from Wuntch. After Wuntch's polite "hello," Holt is already set with his comebacks.

He originally starts by saying the birds stopped singing when she is at the precinct. When she says they are under investigation, Holt retorts with the above line that it's a pity she wasn't run over.

"It's Probably Madeline. Cockroaches Release A Mucus-Like Secretion." (6.18)

Holt in season 6 episode 18 of Brooklyn Nine Nine

It's always fun getting the opportunity to call your arch-nemesis a cockroach. Holt saw the opportunity and took it with ease. In "Suicide Squad," the squad has no choice but to ask for help from the people they dislike most. That's also including the Vulture and Wuntch.

While finishing up the game plan, Jake gets excited over being able to call themselves the "Suicide Squad" and wants a quick huddle. But Charles realizes someone's hand is sticky. C.J. says it might be him, but Holt has other ideas. He claims it's Wuntch because she's a cockroach. Wuntch tries to fire back but it's not as good.

"I Need A Witness In Case Her Head Starts Spinning Around, Or She Turns Into A She-Wolf." (2.14)

Rosa and Wuntch in season 2 episode 14 of Brooklyn Nine Nine

In "Defense Rests" Wuntch goes to Holt for help. Holt learns that she plans to move away from Brooklyn to another police force and asks for a recommendation. When she first appears in the precinct, Holt asks Rosa to stay as a witness.

He says the above line. Fans of the horror movie genre would understand perfectly what Holt is referring to. He's comparing Wuntch to the scray possessed girl from The Exorcist known for spinning her head. Talk about scary and giving the creeps. What better way to describe Wuntch.

"Describing Your Breakfast." (3.01)

Holt in season 3 episode 1 of Brooklyn Nine Nine

To better understand this insult, viewers have to watch the whole scene unfold. Holt is transferred to a new precinct and is greeted by Wuntch. Holt is at the ready when he tells Wuntch that it was nice of her to greet them. He was sure that she was still crushed under the house in munchkin land.

RELATED: Brooklyn Nine-Nine: 5 Times Captain Ray Holt Was The Best Boss Ever (& 5 Times He Was The Worst)

Wuntch is unphased and says "Stick and stones, Raymond." But Holt won't let her get away with it and retorts, "Describing your breakfast." Hook, line, and sinker.

"And Mine Is A Fork-Tongued Lizard Witch." (3.04)

Holt face to face with Jake

Sadly, Wuntch wasn't there to receive the burn of this insult from Holt. In "The Oolong Slayer," Jake asks Holt for help in finding a serial killer. As they investigate, they end up getting suspended by Wuntch and The Vulture. However, Jake and Holt decide to defy their bosses' wishes and decide to meet in secret.

Although Holt is hesitant to do so, Jake manages to convince him by referencing their terrible bosses. The Vulture has tried many times to ruin Jake's career and personal life. Holt feels like he could relate to the situation, comparing Wuntch to a "fork-tongued lizard" with the added bonus of a "witch."

"Yes, I Never Thought I'd See You This High Without A Broom Under You." (2.22)

Captain Holt and Madeline Wuntch in Brooklyn Nine-Nine

It's clear that Holt thinks Wuntch is as evil as a witch and used it to his advantage in insults. When Jake, Holt, and Boyle needs resources to catch a killer, they ask Wuntch for help and go to her new office to speak. Wuntch gloats about her new office and about it being on the 20th floor.

Holt agrees that the office is nice. However, no compliment goes without an insult for Holt. He explains that he would have never imagined Wuntch being so high in the sky without the need for her broom. Holt's ability to keep a straight face makes it even more hilarious.

"The Only Way I'm Going To Die Is If You Touch Me With One Of Your Boney Fingers And Drag Me Across The River Styx, You Reaper." (6.18)

Holt talking at Wuntch

This insult also comes from the "Suicide Squad" episode. There are many complex levels to this insult that need to be analyzed, but, by the end, it's an incredible burn. The scene unfolds by Jake and Holt going to Wuntch and asking for help. She says how withered his face had become to which Holt reports with now understanding why Jake called it a "Suicide Squad."

Holt still wasn't finished. In fact, he then goes on to give the best and most complex insult. He makes fun of her boney fingers and compares her to the Grimm Reaper. The way Braugher delivers it is just perfection.

"Care To Sit? I'm Sure You'd Like To Take Some Weight Off Your Cloven Hooves." (2.23)

Holt in season 2 episode 23 in Brooklyn Nine Nine

In "Johnny and Dora," Holt tasks Gina and Terry to gather a letter that could prove Wuntch conspiring against him. In the interrogation room, Holt is less than courteous and as he says the above insult. He refers to Wuntch having cloven hooves and Wuntch takes it as Holt calling her the Devil.

RELATED: Brooklyn Nine-Nine: 5 Times Captain Holt Was The Worst (& 5 Times He Was The Best)

But Holt had a different meaning. He was simply calling her a goat. If analyzing the insult more, there is a version of the Devil that is portrayed as a goat.

"Boston? But It's So Close To Salem. You Do Know What They Do To Witches Up There, Don't You?" (2.14)

Holt in "Defense Rests" of Brooklyn Nine Nine

Holt can write an entire book on his best insults about Wuntch. One of Holt's best insults comes from the episode "Defense Rests." As previously mentioned, Wuntch plans to leave Brooklyn to take up a new job. She explains that she's the front-runner for a job in the Boston PD.

Holt couldn't let this one slide seeing as it was a golden opportunity. Boston is famous for its history regarding the Salem Witch Trials where countless women were accused and killed. Holt brings this up seeing and questions if she's aware of what going to Boston might lead to.

"But If You're Here, Who's Guarding Hades?" (2.02)

Holt and Wuntch in Season 2 episode 2 of Brooklyn Nine Nine

Holt's knowledge of Greek mythology is impressive, especially when it works as ammunition in insulting Wuntch. At the beginning of season two, Holt is surprised to see his long-time rival appear in the precinct to conduct an evaluation. At first, Holt says it's good to see her but the insult comes right after.

He says that if she is currently in the precinct, then no one is there guarding Hades - the God of the underworld. Essentially, he was basically calling her dog since Cereberus was guarding the gates of hell. Simple, yet effective.

NEXT: Brooklyn Nine-Nine: 5 Reasons Detective Lohank Is The Worst (& 5 Reasons It's Teddy Wells)