Adult Chris: [v.o.] Since I knew nothing about being cool, I decided to consult with the coolest guy I knew to find out his secrets.
Jerome: Hey, little dude from across the street. Let me hold a dollar.

Rochelle: Julius!
Julius: What's going on?
Rochelle: This is what's going on. You told me you were going to get rid of that years ago. Instead you just hid it from me?
Julius: It wasn't hid.
Adult Chris: [v.o.] Yes, it was.
Rochelle: It was underneath your camouflage jacket. It was camouflaged!

Adult Chris: [v.o.] Now before you go getting all upset, in 1986, almost everybody smoked. People didn't give a damn about health. Here's a partial list of things in this picture that people didn't know where dangerous. No sunscreen. Carcinogenic hair gel. Trans fats. And high fructose corn syrup. Eventually, all these people died horribly, but while they lived, they were cool.

Greg: Chris gave it to me.
Ms. Morello: Chris? I'm so disappointed in you. I know that nicotine, pork rinds and malt liquor are the Black man's vices...
Adult Chris: [v.o.] You forgot White women.
Ms. Morello: ...but why infect Gregory?

Chris: I'm a lookout. And if the cops come, I'm supposed to blow this whistle.
Greg: Dude, that makes you an accessory before, during and after the fact.
Chris: I know. I don't even want to be here. But I'm kind of stuck.
Greg: You got to think about this, Chris. My uncle was a lookout one time, and he ended up getting shot in the throat.
Chris: In the throat?
Greg: Yeah, he didn't die, but he ended up wearing a turtleneck for the rest of his life.

Adult Chris: [v.o.] Before I went ahead with being a lookout, I got a second opinion from Doc.
Doc: And they want you to be the lookout?
Chris: Yeah, I mean, I don't want to do it, but these kids like me and I've come so far on my coolness. And I'm just the lookout. I can't get in any real trouble.
Doc: Wrong. You don't know nothing about crime, do you? You act as a lookout, while something felonious occurs, that makes you an accessory.
Chris: Yeah, but I'll still be cool, right?
Doc: Wrong again. There are a lot of subheadings to being an accessory. You can be an accessory before the fact. You can be an accessory after the fact. Or you can be an accessory during the fact. In any event, if you get caught, you going to jail.
Adult Chris: [v.o.] Doc spent three to five as an accessory.

Chris: What do you think makes a guy cool?
Jerome: Cool? Man, nothing makes you cool. You either cool or you're not.
Chris: But what if you're not born cool, and you want to be?
Jerome: Well, the fastest way is to associate yourself with cool people. That way you're cool by association.
Chris: But why would they want to hang with me?
Jerome: Look, man, it starts with attitude, all right? Followed by a little head gear. Accompanied by the walk.
Chris: The walk?
Jerome: Yes, man. All right. The walk. You got to put a lean in your walk, man. You know, like you're slightly bothered by an old gunshot wound to the hip. Like this.
Adult Chris: [v.o.] Easy for him. He had a gunshot wound to the hip.

Tonya: Just thought I should tell you about my day.
Chris: What about it?
Tonya: Oh, I just sat around the house by myself, answering phones, taking messages.
Chris: Good for you.
Tonya: Yeah, I talked to Grandma, Uncle Michael, the principal from your school, Daddy...
Adult Chris: [v.o.] Never underestimate the power of the Devil.
Chris: Wait a minute, did you say the principal from my school?
Tonya: Yeah, you know, they always call when they suspend somebody from school for having cigarettes.
Chris: Did they think you were Ma?
Tonya: I don't know. I just answered the phone and they started talking. You out three days... I guess that's a total of $15.
Chris: What is?
Tonya: Five dollars a day. You know it's going to cost to keep my mouth shut.
Adult Chris: [v.o.] The price of being cool was steep, but it beat the price of being beat.

Manny: You know, you could do this yourself, Julius.
Julius: Yeah, but every time I do, I nick my head.
Manny: You know what's going on? You got a lot of bumps back here, man. Lot of lumps in the back of your head, man. My grandmother used to read these things, man. The configuration is telling me you got a lot of tension.
Julius: Yeah, well, that's true.

Adult Chris: [v.o.] At 15, I was sick of being a nerd. When you're a nerd, people you want to pay attention to you ignore you, and the people you wish would ignore you, pay attention. And I was done with it. From now on, I was going to be cool. Cool guys got everything: girls, cars, girls, money, girls. But what exactly is cool? I tried the surfer look. I tried the superhero look. I tried the cowboy look, but I ended up with the Village People look. No matter what I did, I ended up looking as cool as a fat guy in a sweat suit with a herringbone chain.