Comedian, writer, and actor Dwayne Kennedy is truly a comedian’s comedian. He has appeared on screens and stages since the 80s, getting his start in Chicago at the open mike at Zanies on Wells Street. He’s had guest spots on sitcoms like Seinfeld and Martin, and his TV debut itself wasn’t too shabby: in 1989 he guest starred on the show 227 playing opposite fellow visiting actor Halle Berry.
After years of work in the clubs, he won the 2002 Best Comedian award at the U.S. Comedy Arts Festival, and appeared during that era on the Late Show With David Letterman. He’s also written and produced for television (FX’s Totally Biased With W. Kamau Bell, the 2013 Arsenio Hall Show reboot). Last year, Kennedy won an Emmy award as the supervising producer for fellow comedian Bell’s CNN series United Shades of America.
He’s probably the most successful Chicago comedian you’ve never heard of, and I think everyone in this city needs to buy his new album Who the Hell Is Dwayne Kennedy? (Oak Head Records) and pick up his 2016 EP Oh No! It’s Dwayne Kennedy and sing his praises alongside me. Here’s why:
His home base is still Chicago
Kennedy grew up both on the south side and in the south suburbs, and frequently works into his comedy the kind of analysis about the city-state and community development that longtime Chicagoans can relate to. On the new album (a comedy set edited from three live nights at the Punchline in San Francisco in 2018), he talks about summertime in Chicago, a beautiful time but also “shooting season . . . I don’t know what it is about the warm weather.” He continues, “I’m glad when it becomes wintertime in Chicago and gets to like 39 degrees below zero, because all the gangsters got to go in the house . . . which I feel bad for anyone in the house now getting their ass whupped.” He pauses, then jumps in with precise timing, “but at least now I can walk to the grocery store and get that wheat bread that I’ve had my eye on all summer!”
He’s at the ideal corner of smart and funny
Kennedy’s words on violence, race relations, and social justice are nuanced and thoughtful, and sometimes a train barreling into you that you didn’t hear coming. A recent joke that didn’t make the album (but which Oak Head Records issued on YouTube as a video preview): “I used to let white folks have it . . . let me tell you man, your pathological greed and compulsive need for control has been the single most source of pain and misery for people of color throughout this world for generations! But I try not to say things like that anymore . . . because I’ve found once you have said something like that to a white person . . . you almost never get a second date.”
Other comedians regularly sing his praises
W. Kamau Bell met Kennedy in 1994 in Rogers Park. “It was at one of the open mikes up at No Exit Cafe,” Kennedy told me on a phone call last month. “Kamau was about two weeks into comedy, and I was coming back after a break. I had been there the week before, and he came up and introduced himself and we found some similar sensibilities . . . we’ve been friends ever since.” In 2012, Bell suggested that Kennedy be hired for the writing staff on his FX political talk and variety show Totally Biased With W. Kamau Bell, and comedian Chris Rock (the show’s executive producer) readily agreed when he heard Kennedy’s name, saying that Kennedy was funnier than everybody else when they both were performing at the same clubs in New York City in the late 80s.
He’s consistent . . . and did I mention he’s hilarious?
The new album includes a track titled “The Dog Don’t Bite Unless . . .” in which Kennedy dreams up a seemingly endless loop of ridiculous scenarios where a dog owner is laying down the rules for a new person meeting their big, vicious dog, including “the dog don’t bite unless your heart rate rises above 120,” and “the dog don’t bite as long as you don’t do yoga in front of the dog … don’t do downward dog in front of the dog, because dogs feel like they invented that and they’re not receiving any financial compensation.” Kennedy’s Facebook and Twitter feeds are always a testing ground for snippets of material, and he stays on current topics. Just in the last few weeks, he’s shared his take on the intersection of the Black Lives Matter movement and social liberation alongside musings on the pandemic, and sometimes all in the same biting post—he attributed the quote “No Lives Matter” to “COVID-19” in one, and quotes “White Supremacy” as saying “Black lives matter? What’s next, giving the Indigenous (peoples) their stolen land back?!” Kennedy is the voice that Chicagoans know and the voice that the rest of the world needs to hear. v