Photo: DWAYNEKENNEDY via YouTube
“The fact that Dwayne Kennedy is not a household name is insanity,” Sarah Silverman once said. Having had the privilege of watching Kennedy develop material in person, I have to agree. When I started comedy in the late ’90s, Kennedy had returned to Chicago from Los Angeles, where he had landed a guest-star role on Seinfeld but not made the impact he wanted to in stand-up. The Kennedy you see today, who won Best Comedian at the HBO U.S. Comedy Arts Festival in 2002, was the product of this period of reinvention away from the eyes of Hollywood. A generation of Chicago comedians have been shaped by Kennedy’s example, including Kumail Nanjiani, Pete Holmes, Hannibal Buress, Beth Stelling, Kyle Kinane, and Matt Braunger. In Mike Bridenstine’s Chicago comedy-history book The Perfect Amount of Wrong, Braunger says that the comics in the scene “were all chasing Dwayne Kennedy … He was like Elvis.” Kennedy would “kill harder than anyone else,” according to Bridenstine, “with smarter material than anyone else. And that changed all of them, and the way they thought about comedy, permanently.”
Comics often present political material like they are leading a rally for their own opinions. They declare their position to the room, then ride the applause of those who agree to a perfunctory punch line, giving up on laughs from any dissenters without even trying. Kennedy does the opposite; he carefully chooses his words so the maximum number of audience members will keep an open mind long enough to laugh. The sets he performed during his “reinvention” were packed with intelligent, socially provocative material that could still crush with audiences in the tavern-show rooms of George W. Bush–era Chicago. While he never pandered, he always aimed to entertain everyone present, regardless of their biases. Even if they weren’t brought around to Kennedy’s point of view, they couldn’t help but engage with his ideas. There is no better example than his magnificent 2002 debut on The Late Show With David Letterman.
There are countless professional incentives for one’s first joke on late-night television not to begin with “I’ve been reading the Bible,” yet Kennedy’s characterization of its contents as “wine and stuff that’s hard to believe” earns him a five-second applause break for a setup line. This ovation was not inevitable. Kennedy senses it building, and with the confidence and calm of a seasoned veteran, he stays silently in character and lets it happen, building a reservoir of audience goodwill at the top of his set that a lesser comic might have missed out on in a rush to their first punch line. Crucially for Kennedy’s inclusive approach to “divisive” material, finding “stuff that’s hard to believe” in the Bible doesn’t necessarily alienate anyone. He still has the whole room with him for his first punch line, “I think the wine came first.”
Improv teachers tell students to “play at the top of their intelligence,” but this can be difficult advice to heed when success depends on your joke hitting the most possible tables. Kennedy isn’t worried, dropping “ergo” at the 1:05 mark without a care in the world. He trusts his exaggerated faces, energetic act-outs, and eight distinct character voices will impart any meaning the audience might miss from a word or two going over their heads. Kennedy’s comedy is smart, but it’s also big.
His wineglass is not just a beverage; it’s an integral part of the act. He will hold it as if he is about to take a sip, make a point instead, and put it back down, keeping the audience dialed in and slightly on edge. It’s also the perfect prop for Kennedy’s first act-out when he keeps the crowd with him by enacting a universal experience. Whatever you think of biblical literalism, you’ve probably told a fib while drunk. The audience is still with him when a long sip of his wine signals the piece is complete, earning Kennedy eight seconds of applause.
His next premise requires more information than most. A mini punch line about liking “Negros with spirit” might feel like something he could have cut, but it’s critical to the bit’s success. It earns him enough of a laugh to keep the audience listening for the “Swing Low, Sweet Chariot” history lesson they need for the first punch line to land. And land it does, earning another ovation on “Detroit” at the 2:35 mark. Kennedy could have milked it for longer, but his time is limited, and he has much more to get to in the six-minute performance.
The audience applauds Kennedy’s next setup — a rare occurrence in comedy that happens twice in this set — even though the joke’s subject is slavery, the mere mention of which makes some people uncomfortable. Some try to restrict its discussion, and politicians and pundits attempt to downplay its horrors even today for this reason, but laughter is involuntary — it doesn’t respect the happy fictions we tell ourselves. The audience laughs because they know Kennedy’s slave character, Joshua, is going to die. Whatever tales they prefer be told about our country’s past, deep down they know exactly what slavery was, and the guffaws Kennedy elicits prove it.
Kennedy’s final bit, about the “Global War on Terror” in progress when this Letterman set was taped, is deceptively subversive. He talks about how the U.S. is at war with “an ideology.” Left unsaid is that this means the enemy could include anyone the U.S. designates; Kennedy points out how each war is an opportunity to see what new means the U.S. has to “wipe you out.” The audience can’t help but laugh. They know that despite all the reassurances from our government that these weapons are meant only for our enemies, they would be just as efficient at killing us. Kennedy gets an uneasy little laugh and leaves the topic for a brief tangent to lighten the mood before swinging back around to it 46 seconds later.
“Do you remember … You probably don’t remember … the Revolutionary War?” Kennedy asks. Like the earlier “Negros with spirit” line, this laugh keeps the audience engaged for the extra-long setup required for another ambitious premise about the personal touches of previous wars, like musical accompaniment. Kennedy’s bohemian jazzman bugler and no-nonsense bass player, both unnerved by their booking in a war zone, feel like something out of a Jay Ward Bullwinkle cartoon and provide a needed infusion of playful energy. But underpinning even these broad laughs is the uncomfortable truth that our culture normalizes war to the extent that we have produced a whole songbook full of time-honored music to kill people to.
Returning to the subject of America’s ever more destructive arsenal, Kennedy plays on the audience’s fear. The intelligent weapons he describes are looking not for our enemies, but for “your house.” Kennedy personifies both the swaggery smart bomb and the terrified kid. “Have any of you kids seen Dwayne?” the missile asks. The targets of this war on an ideology have apparently expanded to include comedians with dreadlocks who talk about slavery on CBS. When the frightened child rats Kennedy out, the bomb responds with a banal “Stay in school,” emphasizing how thoroughly Bush-era America equated good citizenry with militarism.
No matter what one might profess in public, contemplating the raw destructive power that exists in the world is never reassuring. Like the little boy who points out Kennedy’s house to the missile, we often feel the best we can hope for is that that power is pointed at someone else. This insight into the anxieties of 21st-century life earns Kennedy ten seconds of applause and his Letterman debut a place among the most successful performances of controversial stand-up material in television history.
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