It might be a bit dramatic to say that Popstar: Never Stop Never Stopping is the best comedy of 2016, but it’s a film that features Nas making a joke about The Good Wife, so you be the judge. 

Popstar is about the Style Boyz, a boy band played by Andy Samberg, Jorma Taccone, and Akiva Shaffer that very closely resembles the trio’s real-life group, the Lonely Island. (Where Lonely Island’s biggest hit is “I’m on a Boat,” Style Boyz’s greatest success is “The Donkey Roll,” both a song and a dance move.) The group fell apart though when Conner (Samberg) went solo and became Conner4Real, a Justin Bieber/Macklemore-esque hybrid nightmare, who on top of penning awful songs is a total diva to boot. The fauxmentry meets him on the heels of the release of his second album—an utter failure—and follows him in the aftermath, as he grasps for straws in order to maintain stardom without having to reunite with the Style Boyz. 

That’s where Chris Redd comes in, playing Hunter the Hungry, an up-and-coming rapper who Conner’s manager (hilariously played by Tim Meadows) hires to become Conner’s opening act to bolster sales for his failing world tour. Hunter is a controversial, skate-rapper styled very much in the mold of Tyler, the Creator, rapping about dinosaurs, pranking people endlessly, and being just generally unstable. It takes a lot to hold your own against the Lonely Island, three dudes who essentially created and perfected this type of parody, but Redd destroys it as Hunter—and he even has some bars! 

The Chicago-based comedian, who has also had some small roles on Empire and Chicago P.D., jumped on the phone with us to talk about parodying Tyler, working with the Lonely Island, and Angelina Jolie. 

How did the Lonely Island guys find you?
The audition process, like anything else. But this one was four auditions and the first time they had me go in I was like, “Oh this is everything,” because I used to rap before I got into comedy. They were looking for a famous rapper at first, but they needed someone who could rap and bring the funny, and those things worked out in my favor. I went in, and they had a couple bars on the page and some scripts, and they were like, “You can freestyle if you want.” So I freestyled for like 20 minutes straight. It was soooo long. I mean, [the casting people] were laughing the whole time. They called me back for another one and I got on the phone with all the Lonely Island guys. They were all talking to me: “Yo, we love what you did on the first one. You can rap again, but like, you know, just don't do it so long.”

What was it like working with those guys?
Very surreal. I was a little nervous for rehearsals and stuff. [But] Andy and I immediately started talking about basketball and I was like, “Ah, okay, I kinda feel comfortable.” They are all just real good friends, so that radiates throughout the different relationships they have on set. I was always a fan of their stuff, so to be able to work with them was a pleasure. I learned a lot. I would go on set when I wasn't even shooting shit and just watch and study 'em because they play stupid so well—they could be scientists about stupid. 

There were SO many celebrity cameos in the film—do you have any weird stories from the set? 
I'm very outgoing—I talk to everybody and anybody on set—so I'm always joking and shit, but Angelina Jolie comes on set one day with her kids. Casually! No one told me she was gonna be there. Also, I didn't know I was such a big fan of Angelina Jolie until I saw her in person. Every Angelina Jolie movie ran through my head and I froze. I was by the sound guy, and everybody was like, “We made a chair so you can sit next to her and talk to her.” And I was like, “I can't form words.” So I just stood by the sound guy. I couldn't help but stare at her all day. Then, she comes up to me and asks, “Hey, you know where I can get some water?” I forgot what water was; how water becomes a drinkable source. I didn't know anything. One of the PAs helped her out, and I never said anything to Angelina Jolie besides, “Uhhhh.” 

Talk to me about Hunter the Hungry, how involved were you building the character? 
They had an idea of what they wanted, but they let me make up his backstory and it was a ton of improv. It was a balancing act of channeling Tyler, the Creator, my own crazy, and DMX a little bit—but trying not to be too DMX. That was the whole point, not to be too DMX. And they let me pick my weird tattoos! 

Which was the weirdest one you picked on purpose?
[Laughs.] There was one that we changed to my self-portrait that was originally a Drake Hand and under it it said, “I found the key to success and then I hid that shit.” And there was another one that was a wolf dragon all across my chest, shooting lazers out of its eyes. 

I saw Hunter as a deep parody of Tyler. How was he as an influence, and how'd you mix DMX in there?
They're both very deep-voiced dudes. And when I get excited as a stand-up, I tend to yell. So between those two inflections, DMX just lives in that world. So I would find myself doing scenes and I was like, “Ah, I sound too DMX right now.” But Tyler was more the way to go. He's into skateboarding, he doesn't give a shit about anything, he's a crazy dude. I was living more in that world. They would be in the same crew. 

Was that a note from the Lonely Island?
The catalyst was Tyler all the way. That's who they wanted to really model off. They're huge fans of him. That man really has no limits to what he'll do. He'll say whatever, he doesn't give a shit about anything. And Hunter's crazier. 

Were you involved in writing the lyrics of Hunter's songs?
Nah, besides like an ad-lib here and there, that was all the guys. They sent me tracks. I heard where Jorma [Taccone] was rapping as Hunter. It was good. It was like really good. One ad-lib that I can think about right away is in a song called “Hunter the Hungry, Hunter's Going to Eat.” I added in the chorus, “I'm fucking hungry!" I wanted him to be mad, but also [literally] needing a meal. [Reed assumes DMX's inflection.] I'm angry, but I also need nourishment.

And there's the DMX.
Yeah, exactly!

Do you know if Tyler's seen the movie?
No I don't know. I hope he sees it. I hope he likes it. And I hope we do a track. 

You can just become part of Odd Future.
Exactly. I just hope to work with all the artists we made fun of.