Chris Redd on Chicago, Style, and his Favorite SNL Character

Careful what you ask Chris Redd in an interview, because Chris Redd, comedian and SNL cast member, will ask it right back. He plays ping pong with words and phrases (he initially wanted to be a rapper). He responds to questions like someone trained in the art of improv, where the golden phrase is “yes and…,” never “no,” lest you end a scene prematurely. He’s naturally funny (as in: you can tell he’s not even thinking about it), and so engaging he could get an upside down tortoise to laugh. But perhaps his greatest gift — the reason he flourishes in front of live audiences — is because he doesn’t just throw out stories into the ether; he makes you feel like a part of the back-and-forth. To answer how would be to give away the secret sauce that’s inherently baked into his being. And also, I have no idea; I’m just here to ask the questions. 

Below: Chris Redd on style in the stand up scene, Chicago’s influence on his comedy, and how a trip to 7-Eleven resulted in his head-down push toward success.  

Bonobos: Stand up comedy has this ongoing joke about how comedians don’t have great style, but I feel like that’s become an old trope. What do you think about that?

Redd: Well, it’s funny, because when you have style in comedy, it kinda goes against what comedy is to a lot of the past generations. You don’t show up fly to open mic. You know what I’m saying? Because then you’re putting too much focus on that and not enough on your jokes. Especially the Chicago scene, it was almost like you [got] more respect for your jokes if you were in a hoodie or some dusty sandals. If you came in a full suit, they’re like, “You cannot possibly be funny. Things are going too well for you.” You can’t be looking like things are going too well. It’s like you’re less funny if you’re doing a good job at life. Comedy’s for the broken and fashion’s not for the broken. But I think what this generation has shown is that you can be fly and broken.

Especially in the black culture, we come fly, even if we don’t have a dollar. You can look how you feel, for real, in your heart. And I like to be fly. I like fashion, and I can tell jokes, so, I’m just going to be fly and tell jokes.

Has that sense of style always been a part of you?

It’s always been inside. I was doing it wrong at times, for sure. I couldn’t afford the things, the idea that I wanted, so I’d grab my dad’s shirt here or some other old shirt here. Trying to mix the styles up and just get it wrong. I made choices … fashion’s experimental, so you got to take shots, and I was taking shots. Maybe the wrong ones, but I was taking them.

Do you feel like you’re taking shots now? Do you feel like you still have things that you put on and you’re like, “I don’t know. This is a bold move, but I’m gonna go with it.”

Yeah, that’s why I have my homies who make clothes around me. They’re into fashion, so they’ll push me in a direction I wouldn’t normally go. And my stylist, Corey DeMon Williams, he helps me take chances. I could wear all black all day. I love how that looks. I love how it feels, but I also love color, so in the past couple years, Corey has been getting me to try different colors and figure out what I like outside of just the monotone.

Who is your favorite person to play on SNL?

Oh man. Kanye [West]. Kanye’s my favorite. Because he is wild. He’s unpredictable, and he’s complex, and he’s emotional, and he’s a genius, and he’ll make you mad, and that’s like, the perfect soup of the things. It keeps that person interesting. You know what I mean? I’m an actual fan of Kanye. So, it’s real cathartic if I hate a decision or thing he said; I can write a joke about that shit, and just be able to tackle that. That’s a cool thing, I think. 

I do love playing Soulja Boy a lot, too. That was a blast to play because I knew the crowd didn’t know him like that but they still went down for it. It was really fun.

Were you one of those people growing up who just had that urge to perform?

Yeah. Well comedy, I wanted to be good at it so I could talk to girls, really. When I first started. Because I wasn’t tall, so I was like, I got to make her laugh. Then later on, I saw it as a thing I could actually do.

You hear about people in your field who refer to themselves as comedy nerds, just consuming it non-stop. Were you like that?

Yeah. I was listening to comedy Pandora stations. I had albums. My dad had the Richard Pryor album; that’s the first album I listened to, “Live on the Sunset Strip” — all of them, really. And then I would watch specials. Anytime a special would drop, I would watch. But I just love comedy. It wasn’t until I was twenty-two that I even thought it could actually be a career. I was rapping, I wanted to rap. So, I always looked at comedy as this other thing I can just kind of do — as a personality thing that enhanced my rap persona.

When did it feel like, “This is real. I’m doing this?”

I went to an improv class, and I didn’t leave. After a bunch grown adults pretended to be trees. I didn’t feel like, This is stupid as hell. I was like, Damn! This is kind of cool.

You’re from Chicago. How has that influenced your comedic style?

Chicago [is] a big part of how I do comedy because I learned how to do comedy there. We have good story tellers in Chicago. Just great narrative jokes. We have a lot of good character types in our city, so I guess our comics tend to be able to tell stories really well, do characters really well. Because it’s an improv city too, and it has a lot of sketch, and it has that rich history there, so I think it just leads us to have a stand up style that really takes advantage of character work, and being able to pull people in, and paint the world in a certain way.

You spoke about telling stories; what is a story that’s important for you to tell or share?

How I got to [this] point… I didn’t start this until I was 23. I just never saw myself doing this. So, to tell the journey, I feel like it can help other people who might’ve felt like me, you know? That look like me. Little black kids being able to go and do sketch, and see that as a possibility. I taught kids in those programs at Second City, that knew about Second City; I didn’t even know about it at all growing up. I had no idea. If I had, I could’ve been in this so much earlier.

The kids are amazing, too. They’re so good. It’s crazy to have that knowledge base. [To] have somebody that represents you in the space that you don’t really see enough of you is a powerful thing. Comedy saved me, so if I can do that for somebody else that’d be dope.

What’s a piece of advice you received that you’ve carried with you.

We were riding to the studio, me and my friend Marcus, and we stopped by the 7-Eleven. This dude walked out…and he was driving this dope — I think it was an Audi — brand new, and he was young. 

I was like, “How did you get this?” He was like, “Yo man, honestly, I just cut out anything that wasn’t about the work for three years, and I just went hard for three years. From sun up to sun down.” When I started comedy, I was like, “I’m going to give this three years, I’m going to do that plan.” After three years, I was like, “Okay, I got to do more.” I was already getting paid, and wasn’t a lot, but it was enough evidence to show me I was on the right path. And I just kept repeating that, extending the years. If it wasn’t about comedy, if it wasn’t about building towards that, if it wasn’t about a show, or learning, then I wasn’t about it. I was very strict about it. Because I wanted to have an Audi. I ended up not getting an Audi, but I had a career. I was building a career; it was way more important. 

Listen to Chris Redd’s comedy album, But Here We Are. Follow Chris Redd on Instagram, @chrisreddis, and Twitter, @Reddsaidit, where he posts show updates, guest appearances, and more. 

Amelia Diamond is a writer and creative consultant. Follow her on Instagram, @amilli0naire.