Talking with Dwayne Kennedy about life, comedy and his new album

Dwayne Kennedy album cover

Dwayne Kennedy is both a local Chicago comedian and a national celebrity. He’s an influential voice when it comes to social and political issues, but he also enjoys silliness. In 2016, he released his first album, although he’s been a successful stand-up for thirty years. He has things to say that might be uncomfortable to hear, but he’s one of the people I’d most like to stand with at a party. He can be reclusive, but the fame train won’t let him disembark even though sometimes he’d like to pull the emergency break.

Writing for, David Gavri called him “legendary” and “a major influence” on Chicago comedians. In an interview with this blog, Tim Barnes mentioned Dwayne, saying he is a “comedy legend.” On the WTF podcast, Marc Maron described him as “mythic.”

Dwayne first did stand-up at an open mic at Zanies when he was around nineteen years old. In a full circle moment, he returns to Zanies to headline four shows this week, this time at Zanies in St. Charles from Thursday March 31 through Saturday, April 2.

Between that open mic at Zanies thirty years ago and this weekend, Dwayne has accrued comedy, acting and writing credits that are truly legendary and mythic. Early on, he was invited to perform at Bernie Mac’s stand-up showcase in Chicago and he also appeared in two of the greatest sitcoms of all time, Seinfeld and Martin.

In 2002, he won the award for Best Stand-Up Comedian at the famed HBO Comedy Arts Festival. His comedy has been featured on The Late Show with David Letterman, Late Night with Conan O’Brien, Jimmy Kimmel Live, Comedy Central’s Premium Blend, Comedy Central Presents and Showtime.

He was a writer for The Orlando Jones Show and The Arsenio Hall Show and a writer and on-air correspondent for the critically acclaimed Totally Biased With Kamau Bell, which was executive produced by Chris Rock. (Chicago note: Dwayne and Kamau Bell met here during their early open mic days.)

In between gigs, he often retreats to Chicago and may drop out of sight for a while and while others would be forgotten, Dwayne never gets too much down time because the national comedy scene always comes calling.

Dwayne’s album, Oh No, It’s Dwayne Kennedy!, is available on Amazon, and iTunes. The album showcases his trademark brilliance and range. His topics include verbal tics, ring tones, slavery and Chiraq.

Dwayne kindly took time out to speak with me by phone about this election year, his storied career, his plans for the future and why he sometimes feels it’s necessary to retreat.


Q: George Carlin, Richard Pryor and Bill Cosby are some of the comedians you’ve said inspired you growing up. What was it about them you found most compelling?

A: Well, when I was a kid I liked Bill Cosby. I thought he was very entertaining and I liked his routines about childhood, but as I got older I gravitated more towards Richard Pryor because he was more raw and real. I don’t want to compare him to Cosby. Pryor just had a different reality. He seemed edgier and he was more honest about his failures and frustrations. It seemed more personal in that regard.

Q: Bill Cosby was my favorite comedian growing up starting out with Fat Albert on Saturday mornings and then I moved on to his stand-up. But I haven’t been able to listen to his comedy since all the news started coming out. I’m conflicted. Do you think the art can be separated from the artist or do you think his comedy died as well? Or can it die?

A: Well, I don’t know if it will die, but certainly it’s taken a hit. Maybe in fifty, one hundred years, people will draw a distinction between what he’s done and what he’s created. I think it will take some time to be able to appreciate him as an artist without all those conflicting emotions. I’m thinking of composers who have been involved in scandal but as time passes, sometimes those things diminish. Not the significance of the deed, but the memory of it. Who knows what’s going to happen? But it’s going to be a while before people are able to hear Bill Cosby the artist without thinking about Bill Cosby the person.

Q: When did you know you wanted to do stand-up? Did you know you wanted to do political and social commentary or did it change over time?

A: I remember watching it on television as a kid and wanting to do it. I put it aside, but then as I got older, decided that maybe I wanted to give it a try. The political and social thing just evolved. I have things to say that might be considered social or political commentary, but not everything I do involves that.

Some of it is relationship stuff, you know, just personal things, as well. Although I’m thinking that actually the very first bit I ever did was about the Black student union at college, so maybe even then I was aware. But as you go on, your point of view becomes sharper and more refined. You start to lean more in a particular direction and realize what you gravitate to and what interests you. For me, it’s more social than political.

Q: Is there a particular topic you’re working on now?

A: No particular topic. You have to talk about the election a little bit. I’m interested in it less as a topic, than as a mood to be captured. I’m interested in human behavior and what motivates people’s behavior. I wrote a long post on my Facebook page about Donald Trump.

Q: I read it and I’d wanted to ask you about that!

A: I was compelled although I don’t consider myself a political writer. But that was just so compelling. It’s so glaringly obvious that when you court the worst of human nature, when your platform is based on appealing to the worst of human nature and it comes back to bite you, how can you be shocked?

Q: Yeah, it reminds me of a horror movie where you think monsters might be in the basement, then they start coming up the stairs. Now they’re coming up the stairs.

A: Right. You know, you handle a dangerous snake and all seems cool until the snake turns on you.

Q: Where do you think this ends? Even if he doesn’t get elected, it seems permission to engage in racism has now been granted. If he’s not elected president, will it get better or does it just progress and get worse?

A: That’s a good question. I wouldn’t be shocked if it did get worse whether he’s elected or not. I think certainly if he’s elected there’s a greater chance of things getting worse because now racists think there’s tacit permission to act of their own ill free will. I don’t know. Maybe if he doesn’t get elected, this will just serve as a cautionary tale. Maybe people will have the chance to reflect on things and it might cause people to re-assess and re-evaluate and pull back, but I have no idea.

Q: You can probably tell, I’m not a very optimistic person. I like the idea of it being a cautionary tale. Otherwise, I’m already envisioning people knocking on my door saying the Jews have to get out.

A: It’s gone bad. It can certainly get worse. If you’re Jewish, Black or anybody who’s non-white male Aryan, whoever they are, I think it’s fair to extrapolate how bad it could possibly get and, right, with some folks they have history of that, there’s evidence of it, of how bad it can get. There are reasons to think like that.

Q: Once you have someone who’s dividing people into “us” and “others,” then you really don’t know where it’s going to go. But hopefully, I’m just a worst-case scenario person.

A: Hopefully. But I really can’t blame you. It has to be considered because who would have thought it would have even got this far?

Q: Right. It was funny last summer. Now it’s not funny anymore.

A: No, it’s not funny anymore. It was a different time, of course, but when Hitler and Mussolini came to power, there was a time early on in Hitler’s career where people didn’t take him seriously. There were very few people who gave him much chance of doing anything and then look what happened.

Q: Do you think this is just human nature or do you think at some point in the evolution of humans, racism won’t be as much of a concern and people won’t have to watch their backs anymore?

A: In every human being there can be good or evil. Some are more prone to one or another, but I think there are a lot of people in the middle that just move with the status quo. In Nazi Germany, some of the people who were in the army said, “I was just doing my job.” I think a lot of people are in that hazy place where if it’s fine with the status quo, they’ll concede even if they don’t necessarily believe in the thing that the status quo is espousing.

Q: It’s weird. It’s like their mind is just a blank space waiting to be filled with whatever.

A: Right.

Q: Sorry, I don’t mean to be a downer.

A: In light of what’s going on, it has to be considered.

Q: Our country doesn’t have the best track record. We like to hold ourselves up like we do, but we don’t really.

A: No. Not really. Look at the Japanese internment camps and just everything. So many things.

Q: Now people are getting punched and shoved at Donald Trump rallies …

A: Right, if it’s there now, what happens if he gets elected?

Q: Yeah, it’s scary because even if he “claims” he’s not a racist, he says things to incite racism. People who want to hear permission are hearing it and he’s not speaking out against it.

A: Exactly. Right, he’s certainly accommodating and appeasing the racists. Whether you’re racist or not, if you’re amoral, that’s just disaster waiting to happen. If you don’t take an active stance against those things and you give permission for those things to flourish it doesn’t matter what you profess to be.

But people are keenly aware of what has happened in the past and what could potentially happen. I think that’s why you’re seeing such vociferous protests against him. People are not just standing by or allowing it to happen without any sort of obstruction or defiance.

Q: That’s a good point. That really is where it’s different.

A: As Hitler came to power, people didn’t take it as seriously as they might, but now with those examples, people are taking it much more serious now. Certainly not like last year when everything seemed like a joke. I don’t know if there’s anyone who takes it as a joke now.

Q: That makes me feel more optimistic. Maybe it will end as a cautionary tale like you said.

A: Hopefully. But if he’s elected, then we’ll see what happens. There have been times in history when politicians espoused certain beliefs in Congress or as governors and got into the White House and did an about-face or advocated an ideology nobody ever expected. Lyndon Johnson was never big on civil rights when he was in Congress, but once he became president, he was one of the greatest civil rights presidents of our time.

It might be wishful thinking to think Donald Trump could become a peacemaker and a diplomat once he gets into office or do an about-face on some of the things he’s espoused.

Q: Maybe this is all a ruse.

A: I tell the joke that Donald Trump is a government operative used to flush out who all the bigots actually are.

Q: Get them to come out of the shadows and then maybe he’s going to deport them.

A: Right! Maybe that’s the deal.

Q: Well, that’s definitely cause for optimism.

A: [Laughing] Yeah. I got to say delusional.

Q: Speaking of topics, I really loved your album. How did you decide where to record it and on the title?

A: First of all, thank you. I’d been wanting to record something for years. I’ve recorded stuff that I didn’t like or the sound wasn’t right or I didn’t feel right about it or whatever it might have been. I just decided I at least wanted to do something, say something.

I recorded it in Grand Rapids, Michigan, at this club I had visited earlier that year. I really enjoyed the show I had there, so I decided I wanted to go back there and record a show. So that was my decision in doing that and the title, I just thought it would be funny.

Q: Which are your favorite tracks?

A: I think my favorite track is about if slavery were still legal. Oh, and I like the one about being broke and trying to raise money by trying to get wrongfully convicted.

Q: I love those.

A: I plan on recording another one sometime this year. So probably what I’ll do is expand on some of those bits and add new material. I just wanted to dip my toe in the water and see what it’s like to do this, so that’s why I put out something.

Q: I really enjoyed it. I’m excited there’s going to be another one soon.

A: Thanks.

Q: You mentioned that you’ve recorded a lot of material in the past, but decided it wasn’t the right time to release it. What about the previous ones made you not want to use them?

A: Just compulsion. You always feel like it’s not good enough. Or it can be better. That was always my issue. I know I can do better than this, or this bit is not complete or whatever it might be. Just compulsion. But I decided that I’ve got to do something. You know that expression, you can’t let the perfect be the enemy of the good?

Q: Yeah …

A: So I just got to that point.

Q: I know what you mean, perfectionism, if it wasn’t what you thought was perfect …

A: Yes. So now that I’ve done it, it wasn’t as bad as I thought it was going to be. I certainly want to do it again. Some things will be different. Like with this album it was just one take. A lot of times when people record an album, they use a couple of shows, so you get the best of every bit and you can use audience responses and get the best of that, so it gives you more choices. For this one, it was all from one show. Next time I may do it by recording multiple shows.

Q: Very cool. What else does this year hold?

A: I was in L.A. the last month. I’m working with Hari Kondabolu on a project. We worked together on Totally Biased. He came to Chicago last year and we hung out. He told me that he’s got this deal and that he was going to be working on the pilot and asked me would I work on it with him and so you know, of course, my usual response to anything like that is reluctance and no.

Q: How come?

A: Because that’s me with everything. I’m just a reticent person.

Q: I can understand why I am, but not why you’d be. Not to embarrass you … but your writing, the comedy. It’s beautiful. What makes you reticent?

A: I don’t know. I think it’s just my nature. I’m less reticent than I used to be, but I think that’s just my nature. It’s just how I was born. I battle with that. I try to keep myself psyched up and girded and mindful to push forward and not to be so reticent. It’s easy for me to retreat.

Q: Yeah, I understand. This might sound really stupid, but I did a Facebook post this week and it started getting all these “likes” so my immediate inclination was I needed to take it down. Immediately.

A: Yup. I know what you mean. Yeah, like that; whatever makes us do that.

Q: Yeah, I don’t really understand it. I just knew that at first I was really happy with a little bit of attention, but then I’m like, noooo, no, stop looking at me!

A: Right. That’s a good point because I think in some ways because I’ve had a modicum of success some people say, “How come you’re not more famous” or more this or more that? I know some things happen externally that are beyond your control. That’s just going to happen. But I think a lot of what I have or don’t have in show business is completely due to me and my own lack of boldness or bombast or whatever that thing is. So I get your point.

I’d do a show at a club which would be great and if people liked me, that would be cool. That kind of success would be fine, but sometimes the thought of being so famous … You know it’s like you want things and you don’t want things. The idea of being famous is more appealing than the actual reality of it. You get to the point where you think that it can become a reality, that’s when the retreat happens.

Q: Yeah, I think I understand that.

A: So to get back, Hari asked me to work on this pilot and I love Hari. He’s my guy. So I knew I was going to do it, but of course I couldn’t just say that right out. I had to go back and forth and all that stuff, but I wound up doing it.

Q: What’s the show going to be about?

A: Well, it’s Hari’s point of view. His comedy is very social and political. If you ever saw him on Totally Biased, you’ve got a feel for what his sensibilities are. He’ll be the host. It will be sketches and stand-up and man-on-the-street stuff.

Q: That sounds really great. I also wanted to ask you about the art of effective commentary. What are the most important things to do and keep in mind in order to be effective?

A: Well, you have to have your point of view and your beliefs. It all stems from what you believe and how you conceive the world and to present those things in a way that’s poignantly humorous. Now how you do that? Really?

Q: Yeah.

A: I have no idea. [Laughing] But it starts with a point of view or an idea about how things work or how you think things should work. Start from there and shape it into something that’s hopefully funny, but at least entertaining or interesting.

Stylistically, I try to present things as if it’s a conversation. That is something I constantly try to do, make it conversational, even if I am the only one talking. So that is one conscious technique, to make things seem conversational and spontaneous and not stilted or preachy.

Q: From early in your career, what are the memories that stand out about working on shows like Seinfeld and Martin and Bernie Mac’s room at Milt Trenier’s?

A: The thing that stood out to me about working on Seinfeld was how professional everybody was. Everybody was there on time. Everybody worked hard. Everybody was respectful.

I don’t know if you remember some years ago the incident with Michael Richards at the Laugh Factory in L.A. where he used all those racial epithets. The funny part is when I worked on Seinfeld the person who I talked to the most was him. We weren’t tight buddies, but of the stars on the show he was the one I talked to the most.

Q: Was he goofy like Kramer?

A: No. Off camera he was very thoughtful and constantly thinking about the character and working on it.

Q: What do you think happened at The Laugh Factory?

A: I don’t know. I think one thing is he was bombing and it’s just embarrassing to bomb. So sometimes when you bomb you panic. It’s like you’re drowning and you’ll grab onto anything you can grab onto, so maybe he just got into that mode and couldn’t get out of it and wanted to be outrageous and maybe because he was getting heckled, he wanted to hurt that person as badly as he could to deflect some of the embarrassment from himself. But it backfired on him.

Q: What was it like working on the set of Martin? What’s happening on the set when you’re not filming?

A: You get the writers always looking to see where lines can be punched up. Actors looking to see where they can do a line better or differently. People really just worked. So that’s what you get. Real focus on what it is they’re trying to accomplish. Especially the day of the shoot. They’re there ready to work. During the week there might be some looseness. People riffing and trying to find the rhythm and make the comedy better. As the week goes on and it gets closer to show time, people are concerned with things like the blocking and getting ready to do the show. Less cutting up as the week goes on.

Q: What was it like working with Bernie Mac and at his room?

A: He cultivated the type of audience that he wanted. Before the show he would tell the audience that they were to be respectful of the performers. No heckling. No nonsense. So you do that and then you get the type of crowd you want, a crowd that is respectful of a performer. It was great. I did the room three or four times and it just got better each time. So it was a great spot and it was cool because when Bernie was back from touring or whatever he was doing, the energy was high and the room would be packed and people would be there to see him and his guests. It was a good experience.

Q: How did you meet him?

A: Just doing stand-up. I never got to know him well. The times I encountered him most were in that room. I had seen him do stand-up once prior to when he was famous, just go up at a room. But [at Milt Trenier’s] was really when I spoke with him the most.

One time he actually called me because he worked with a friend of mine who wrote for him and opened for him, my friend Ali LeRoi, who wound up creating Everybody Hates Chris with Chris. He called me and asked me to write for him, but I didn’t want to do it because one of the reasons I went into stand-up was so I didn’t have to have a boss, so I could do it myself, and I didn’t have to worry about disappointing anybody. My big thing was I didn’t want to write for him because I didn’t want to disappoint him. I don’t want to write something that you don’t think is funny. I don’t know if my ego could handle it.

Q: I understand that myself. But I can’t imagine you disappointing anyone.

A: I can imagine me disappointing everyone.

Q: How come?

A: I don’t know. Personality. The whole reticent thing. There have been maybe three or four people who have asked me to write stand-up for them and I’ve never really … I probably did it once, but it was more incidental then a formal writing job. You know, it’s a combination of ego and insecurity. I don’t want to disappoint you by writing something that you don’t think is funny, but also I don’t want to hear you say that something isn’t funny. Not that everything is great. But I don’t want to be in that position of subordination.

Q: I think I understand. I don’t like people judging things I’ve written. It’s really painful. I’d almost rather not do it than risk that kind of pain.

A: Right. So that was the reason. But I was flattered that he asked me. I never told him no. I just didn’t tell him anything. I never got back to him.

Q: What was your writing process on Totally Biased? How did you choose your topics?

A: Oftentimes you would deal with what was in the news and sit around talking about it, riffing on it. People might have ideas they wanted to develop or in riffing you might come upon an idea that could be developed, and you would sit around the table and pitch your ideas. Then the head writer and Kamau would say what they liked or didn’t like. If they liked it, they’d assign you to work on it, maybe assign you to work on it with someone.

Q: What is your favorite memory of the show?

A: I loved doing the stand-up pieces on the show and I loved doing the man-on-the-street and the field pieces. I went out with Kamau quite often when he would do man-on-the-street. I loved being there and the lines and questions you come up with on the spot. I loved doing that.

Q: What would you say are the best and worst things that have happened to you as a comedian?

A: The best things are the bits and routines that work and when people appreciate them and like what you do. I would say the worst thing is when a joke falls flat, although that’s not as bad as it used to be. I don’t take it as hard as I used to take it.

So now the worst thing is probably not getting money you’re supposed to get for a gig. That’s worse than a joke bombing, because at this point you know that a joke might bomb, but chances are you’ll come up with one that doesn’t bomb or you’ll be able to fix the one that did, so I don’t look at it as an indictment of my very existence.

Q: I love that phrase. I think everything is an indictment of my existence! What do you think is the state of comedy when it comes to racism? What do you think are the biggest obstacles? Do you think it’s changing and what will it take to really change things?

A: Well, there are a lot of shows being done by a lot of different type of people, like grassroots shows. There are certainly more types of comedians then there have ever been in terms of race and gender and politics and ideas. I don’t know if that’s necessarily matriculated all the way to the top as far as seeing those types of people on TV. I don’t think that it has. I don’t know that it will until there are as many people behind the scenes controlling access to television as there are different kinds of people who are making the comedy.

I think that as long as things are still pretty much white male controlled, that’s what you’re going to get the preponderance of on television. Certainly, it’s changed to some degree, but in some ways not very significantly. Until the faces and the beliefs of the gatekeepers change, then a lot of the other stuff is not going to change.

Q: What’s something unexpected about you that the audience might not guess?

A: Oh, man. That’s a good question. Maybe that my comedy can be abstract or characters. It can be goofy and silly. It’s not only political and social.


Dwayne Kennedy is at Zanies, Pheasant Run Resort, 4051 E. Main Street, St. Charles from Thursday, March 31 – Saturday, April 2. Tickets and more information here.

You can find Oh No, It’s Dwayne Kennedy! on Amazon, iTunes and
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