“That’s the beauty of stand-up,” comedian Dwayne Kennedy says casually, his glasses, goatee and all-black outfit mixing with his contemplative tone to give him the vibe of a philosophy professor discussing a classic text. “You can talk about anything you want to talk about in the world as long as it ends in funny.“
It’s Sunday night, a few hours before the first of seven shows he’ll be performing at Zanies (the Wells Street location) over the next week, and the iconic venue is empty, framed faces of famous comedians staring at us from all sides as we chat.
The weeklong stint at Zanies, which culminates with two shows Friday, is a comedic homecoming of sorts for Chicago native Kennedy, who performed his very first set at Zanies in the ’80s.
“I saw Zanies had an open mic so I came in, signed up, went on,” he says. He did five or six minutes that first time up but thought performers had to bring completely new material to every open mic. “So the first time it went well. The second time was kind of dicey. The third time it was horrible, so then I didn’t do it again for a year and a half.”
After letting his ego recover, Kennedy gave comedy another shot and has been at it ever since, with appearances on “Late Show With ,” “Jimmy Kimmel Live!” and “Late Night With Conan O’Brien.” He consistently opens for friend and former Chicagoan W. Kamau Bell (the two recently appeared at the Park West) and was instrumental to Bell’s short-lived, Chris Rock-executive produced show “Totally Biased with W. Kamau Bell.”
But despite his ties to the coasts and the occasional pull of a next level of career success and opportunity, Kennedy has continued to call Chicago home. “I love it,” he says. “Compared to LA there are a lot more places to work in Chicago. Chicago is a great place to get good. It’s not a place to get famous.”
It’s true Kennedy doesn’t have the type of notoriety that an average audience member (or “civilian” as he calls noncomedy people) will recognize or geek out over; his Sunday night show at Zanies played to a house at half capacity. But among his fellow comedians it’s a different story. Comedian and podcaster Marc Maron described him as “mythic” while Chris Rock said he was “naturally funny.”
“He’s somebody that people know in the comedy world,” comedian Hari Kondabolu told me when I mentioned Kennedy’s name.
Kondabolu -- who also worked on “Totally Biased” -- declared Kennedy the godfather of the current Chicago comedy scene. “When I talk to Kyle (Kinane), John Roy and Matt Braunger -- they were the first miniwave of people coming out of Chicago -- they talk about how Dwayne Kennedy was their idol, he was their guy.”
According to Kondabolu, Kennedy is the kind of comic who inspires other comedians to work harder and be better. The reason Bell has Kennedy open for him is that he’s notoriously difficult to follow. “He’s somebody who in some ways is the proto of this giant decade of comics. He was there before that. He’s still there now,” says Kondabolu. “I can’t help but imagine he’s had some influence. He’s in the DNA of (Chicago). Which is probably a good indication that this is a healthy scene if he’s in the DNA of it. You know, smart, well-written, thoughtful comedy.”
And yet despite his reputation among comics, Kennedy is almost impressively nonprolific in terms of recorded material, with only one EP out — 2015’s “Oh No, It’s Dwayne Kennedy!” When I ask him about plans for future albums -- something he’s hinted at in the past -- he demurs. “I want to do it, man. But I’m compulsive and procrastinating,” he says. “But I really want to get that going. I’d like to have it done before the end of the year. We’ll see.”
Kennedy has been in the game a while, and he takes each new project with a grain of salt, putting the work in without getting his hopes too high. I ask about a show he was reported to be working on earlier this year and he laughs. “I was working on this show, a pilot, that was going to be shot in Chicago,” he says. “And you know … in show business, you either hear ‘yes’ or you don’t hear anything. So we haven’t heard anything, so that might be a ‘no.’ It might be that they put it on the back burner. I don’t know.”
Kennedy has a style of comedy that’s reminiscent of a casual conversation on a front porch, mixing observational humor with deeper topics that would otherwise be tough to laugh at. On Sunday night the South Sider joked to a couple of Canadian tourists that they had traveled to Chicago just in time for “shooting season.” He went on to note that as the cold weather sets in and people head inside, “all the street violence just becomes domestic violence.”
It’s a tough premise to work with, but Kennedy takes it, twists it around and makes it about himself: “I feel bad for anyone getting their ass whupped, but now I can finally walk to the grocery store and get that wheat bread I’ve had my eye on all summer.”
It’s the quirky specificity coupled with his calmly upbeat delivery that makes punchlines like this work, the informal way he addresses the audience, along with his penchant for pausing to consider the crowd. This comfort came with years of practice. When he first started, he felt as though he needed nonstop jokes. “But I felt constricted in the way that I put so much pressure on myself,” he says.
Then one night he decided to go onstage and not say anything. “So I just stood there. And you know, it wasn’t bad,” he says. “The owner hated it. He snatched me off stage early. But, you know, I lived, OK? So you start to realize … you can take your time and you can be conversational. You can have silences.”
Later in Sunday’s show he came back to the tourists and asked what kind of Chicago experiences they'd had on their trip. “Everything,” came the response. Kennedy didn’t believe them. “Did you struggle to pay a light bill?” he immediately deadpanned. “Did you get wrongfully arrested?”
He knows to deliver this last line as a lighthearted irony rather than an accusation. And it’s that friendly bantering tone that gives him free rein to cover thorny issues without coming off cynical or negative. It also helps the depth of his punchlines that he’s not trying to offend. “I think a lot of people are way edgier than me,” he says.
Kennedy has a much more straightforward set of goals: “I just don’t want to be lame,” he says. “That’s all. I want to be funny and not lame. Those are my two goals.”
For Dwayne Kennedy, the quest to be funny without being lame has made him legendary. Comedians know it -- it's time for civilians to take notice.
Dwayne Kennedy is appearing through Friday at Zanies, 1548 N. Wells St.; tickets and more information at 312-337-4027 and .
Zach Freeman is a freelance writer.
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