Dewayne Perkins is working his way up the Hollywood ladder—and is expanding representation for the Black and LGBTQ+ communities in the process.

The Emmy-nominated Chicago native—who is an actor, writer, producer and comedian—trained at Second City before becoming involved in film/TV work. He wrote, produced and/or acted in projects such as Brooklyn Nine-Nine, the rebooted Saved by the Bell and The Amber Ruffin Show, but he might be best known as the driving force (as writer, producer and actor) in the hit horror-comedy film The Blackening, which hilariously skewers ethnic stereotypes.  (Recently, he was involved with the Prime Video limited series Sausage Party: Foodtopia and wrapped shooting a recurring role on Seth Rogan’s new series The Studio, which will be on Apple TV+.)

Recently, Perkins talked with Windy City Times about Second City, Hollywood, Ruffin and more.

NOTE: This conversation was edited for clarity and length.

Windy City Times: You trained at Second City—a place some people really revere. What was that like?

Dewayne Perkins: It was a mixed bag of so much good and so much bad. I met some of my favorite people there—and they’re still in my life. I learned a lot, and it helped shape how I approach the entertainment business. It really helped create a litmus for what I want and what I don’t want. I’m grateful for the experience but I definitely think it could’ve been better.

WCT: Would you care to elucidate?

DP: [Laughs] It was just a very white company run by people who didn’t know how to deal with talented people of color, to be frank. I think during that time, there was a movement to try to be more inclusive without the knowledge of how to do it properly. But I like to focus on the positives that came from that experience and the people I met who became a foundation of support for me as I moved through my career—people like Lisa Beasley and Shantira Jackson. Those are people who are still in my life today, and have been my creative support since I was in Chicago. 

And so many parts of The Blackening started as sketches on the Second City stage. There is a goodness that came from my time there although there’s a section of my Wikipedia page literally dedicated to “the controversy.” [Laughs] Ultimately, it’s … whatever.

WCT: One of the things I found really interesting about you is that your family has been supportive of you since you came out—and there’s that stereotype that Black families are not so supportive. 

DP: Yeah. I came out when I was a teenager—and they knew that I was going to do what I wanted to do anyway, pretty much. Either they were going to get on board or be left behind. I’m thankful that my family has been as supportive as they have; in high school, they came to all of my shows. 

Dewayne Perkins. Photo by Kim Newmoney

WCT: I saw a couple of your stand-up routines on YouTube and I wanted to ask you something. You said that you would defend Chicago to the death as a Black man—but not so much as a gay man. Why is that?

DP: I would say that came from a point of view when I was younger when I felt like I could not be Black and gay at the same time. I felt like, growing up, I was surrounded by Blackness; that’s where my comfort was and I knew that, in certain environments, that being gay was frowned upon. So I always felt a deep connection to Blackness, culturally. 

Then, when I went to college [DePaul University], I recognized that people were more comfortable with my queerness than my Blackness. So [the routine] was a reflection of those different experiences. There’s truth to it but there’s also a little exaggeration because I am a full person and by the time I went to college, I recognized very quickly that—in order to be the version of myself that I wanted—I had to realize that these two things are not separate. I just exist as both at all times—but noticing which environments gravitated toward which sides is always interesting. But that’s where a lot of my comedy comes from—observing [things] based on my identities.

WCT: And observational comedy is one of my favorite forms. There are so many things about life that people either want to avoid or that they just don’t know about—and comedians are truth-tellers.

DP: [Nods] I find humans fascinating. Also, I have a speech impediment so I’ve been in therapy since I was in kindergarten. I was a very therapized child and I realized that people didn’t realize how much self-awareness I’ve had. I’ve always been kind of quiet and observing, thinking, “I’ve been told something but I’m seeing something [else], and these things don’t match.”

WCT: One of the many things I like about The Blackening is that there’s no explanation of stereotypes. Either you know them or you don’t.

DP: Yes, and that’s very intentional. As a person who absorbs a lot of arts that are not necessarily made for me, I think the curiosity to explore what we don’t know is how you grow. So if you don’t know something, look it up. I don’t think it’s my place to teach my identity. The movie is entertainment, and there are certain jokes I’m going to write because I find them entertaining—and if you know, you know. If you haven’t watched Set It Off, there’s a section you won’t understand. And if you see people around you reacting and you’re not, hopefully you’ll be motivated to look up what it means. 

That is how I think I grew as an artist. Watching things that did not include Blackness, I still found the human part of that art that I can attach myself to.  But I think normalizing one’s identity that way is the bridge to empathy.

WCT: Is there going to be a Blackening 2?

DP: It’s being worked upon. I can’t say too much about it.

WCT: A lot of people see the film/TV industry as this bastion of liberalism. How correct is that view?

DP: It’s a very large industry, but I don’t think liberal or conservative is the priority—I think money is. I think it’s a capitalist industry.

How many Black gay men do you see on TV? How many stories are we getting? It’s about money and access. 

WCT: So, as you know, Amber Ruffin recently came out.

DP: Yeah—that’s my girl.

WCT: How did you react?

DP: I commented and said, “We love that gay shit.” [Laughs] I thought it was cool. Just be open to love. There’s just a lack of it.

WCT: On a very different note, I know you’re involved with Sausage Party: Foodtopia. I saw the movie so I’m a little scared to see this.

DP: Oh, no—it’s a good time! It’s a little out there, a little raunchy—but it’s fun. I think that was one of my better jobs. Dealing with anthropomorphic foods—that involved a way that I was not able to write before.I had to really stretch myself and use my degree in animation; it was very helpful.

WCT: Asking you something I’ve asked people over the past year, what is it like for you to be part of the queer community in today’s America?

DP: I think there are a lot of positives. I think the freedom of being able to choose [or be] who you are is something that a lot of non-queer people don’t understand because heterosexuality is so commonplace in society. I feel that when I was younger, there was such a lack of people that I either had to completely crumble or create a stronger sense of self. So that has positioned me to be the best version of myself. But then there’s that part of constantly fighting people who don’t want you to have that freedom. 

I do think the queer community is changing the landscape of society, although it’s not changing quickly enough. I think that very significant changes have been made [regarding] ways that we couldn’t live in the past—and I think that is very hopeful in a time when hope isn’t plentiful.