Madeline Wuntch: Hello, Raymond. How do you like my new office? Twentieth floor.
Captain Holt: Yes, I never thought I'd see you this high without a broom under you.

Jake: Whoo-hoo-hoo! We did it! What? I'm only human. You can't always expect me to be the coolest guy ever.
Bob Annderson: Coolest guy ever? Try telling that to Alan Greenspan.
Captain Holt: Nice burn, Bob!

Captain Holt: Do not trust any child that chews bubble gum-flavored bubble gum.
Do not trust any adult that chews gum at all.
Never vacation in Banff.

Gina: I did a little sleuthing on your rivals. You want me to spill the beans?
Captain Holt: Why would you ever intentionally spill beans? They're one of nature's most densely packed protein sources, and they remain unsullied by flavor.

Captain Holt: I tried to suck it up and go back to work. I put on my uniform and got in my car. And next thing I knew, I was on a plane to Mexico. I didn't even pack a bag. I bought a bundle of novelty shirts at a nearby gift shop.
This one says, "What's up, beaches?" Instead of "bitches" for humor reasons.
Amy: But you hate humor.
Captain Holt: Well, I'm a joke now, so it suits me.

Rosa: You all right, Captain? Tough weekend?
Captain Holt: I went to Barbados with my husband. We wove hats out of palm fronds and swam with the stingrays. I've never been happier.

Madeline Wuntch: Oh, Raymond, that you came to me to ask for help shows how much you've matured. You know what else shows how much you've matured? Your withered face.
Captain Holt: Now I know why you refer to this as a Suicide Squad, Peralta, because I already want to kill myself.
Madeline Wuntch: Why don't you wait a week? You'll probably die of old age.
Captain Holt: The only way I'm going to die is if you touch me with one of your bony fingers and drag me across the River Styx, you reaper.

Madeline Wuntch: Hello, Raymond.
Captain Holt: Madeline. I wondered why all the birds had suddenly stopped singing. What brings you here?
Madeline Wuntch: I heard you were under investigation by Internal Affairs. Didn't wanna miss that.
Captain Holt: So much time with your ear to the pavement, it's a pity a truck hasn't run over your head.

Jake: Wait, Wuntch is dead?
Sergeant Jeffords: Yeah. The Commissioner's office just notified us.
Captain Holt: No way that's true. As Wuntch says when she sees deodorant, "I'm not buying it."
Rosa: [laughs]

Captain Holt: I wish he would turn the radio down.
Jake: You think that's the radio? That sounds like professional music to you?
Captain Holt: All music after Mahler sounds exactly like that.

Captain Holt: I remarked afterwards that I wished the officiant had been more efficient. It was very funny. Kevin still talks about it. Maybe I should open with that zinger?

Sergeant Jeffords: Should I just go tell everyone to buck up and do their jobs?
Captain Holt: No, the squad's only on night shift because they came down to Florida to save Jake and me. It's my responsibility to fix this, so I'm going to brighten the mood by telling a few jokes. Try this one on for size: I don't care for cheese.I'm a curd-mudgeon. [silence] Wow. You're too tired for humor.

Madeline Wuntch: Oh, there it is. The shriveled husk of Raymond Holt.
Captain Holt: Look, Gina, is that a talking raisin?
Madeline Wuntch: Enough foreplay.

Captain Holt: When people say, "Good morning," they mean, "Hello." When people say, "How are you?" they mean, "Hello." When people say, "What's up?" they mean, "I am a person not worth talking to."

Captain Holt: Oh, I see. So the only thing we have to go on is the word of one of your criminal friends?
Doug Judy: Criminals? That's how you see us? Is it a crime to steal bread to feed your family? Or to sell some weed so you can buy video games? Or to steal video games because you smoked all that weed you were supposed to sell?
Captain Holt: Yes, all of those are crimes.
Doug Judy: Damn. Even the bread one?
Captain Holt: Especially the bread one.