“You think people know that Bo Jackson is from Alabama?”
The comedian Roy Wood, Jr. is minutes away from the first of two back-to-back, sold-out shows at New York’s City Winery. Ever the perfectionist, he’s making some last-minute tweaks to his set, asking openers Von Decarlo and Erin Jackson for their thoughts on his closing bit, a joke that requires the name of an Alabama celebrity. (He winds up using Nick Saban instead.) He is electric onstage, an affable monster, blending real-life issues like the pandemic and racism with a biting wit and absurdist viewpoints. But after the show, Roy declares his hour isn’t polished yet. He not only took suggestions from folks in the room during the set, he also had former Daily Show writer Travon Free and Chappelle’s Show co-creator Neal Brennan texting him suggestions on punching up his bits. “He’s never satisfied,” comedian Paris Sashay, who opened for Roy on many shows on his tour, tells me later. “He’s told me before ‘that joke is good, but it isn’t finished,’ and we’ll work on it together. Roy wants to get all the meat off the bone of a joke.”
Wood has been an active comedian for more than two decades. These days you can catch him on The Daily Show, where he’s been a correspondent since 2015, and in appearances on everything from Better Call Saul to Only Murders in the Building. He is known as a role model in the comedy world—someone you want to run your sets with. He’s the guy you ask for help with the packet you submit for writing jobs on late night shows. And onstage, he isn’t there to just make audiences laugh. He’s making them think about real-life issues in new ways. He turns uncomfortable topics like prison reform, and Civil Rights movies into memorable jokes.
When we meet, Wood is also marketing his special: He’sd already been on the road for a month before his taping in Denver, with stops in Indiana, California, and Illinois as well as New York. Direct-to-consumer marketing is a lesson he learned from a legendary Atlanta comic: “I was in Alabama once, opening up for Bruce Bruce,” Wood says, clutching a Dunkin Donuts iced coffee in between sets. “I thought I was hot shit. I did what nobody is supposed to do: time before the headliner. Six minutes.” He pauses and takes a sip. From his cadence and the smirk on his face, it’s clear that this story doesn’t end well for him. “It was one of the most intense sets I’ve ever seen. [But] Bruce Bruce did so well people forgot I was on the show.” He continues: “Bruce Bruce and Lavell Crawford are genius marketers. They would fly down a day before the show and go to malls in the cities where they were headlining. They’d go to black barbershops and talk shit. This was before you can market yourself online. Bruce Bruce would do radio even if the shows sold out. He told me ‘that’s for next year’s show’. He was always thinking ahead.”
Wood landed on the title Imperfect Messenger after his 2017 special Father Figure taught him a hard lesson in SEO practices.“George Michael fucked me up,” he tells me two weeks later, in Indiana, where he’s performing at The Comedy Attic in Bloomington, referring to the singer’s hit song of the same name. “I didn’t realize until it was too late,” he laughed. “If you Google search Father Figure, I’m not on the first page. Fucking George Michael.”
Another proposed title was Same Pain. It makes sense, given Roy’s interest in searing, topical material.“Then I realized Kevin Hart and Chris Rock both used Pain in some of their specials. I wanted to be original, and not seem like I was biting off them.” One of the original ideas for the new special, he continues, was White Draws—as in underwear. “If you wear colored underwear, it hides the stains that may happen. You can see all the shit when you wear white underwear. I was relating it to all the shit that leaves a mark on you in your own life. Then I realized I would get into some weird fetish shit if people searched ‘white draws’ online. (He clearly was reluctant to let it go: “I tell the truth like white draws” appears on his Twitter bio.)
Wood doesn’t take two steps in Bloomington before being recognized. The proprietor of Popkorn, a black-owned popcorn shop, reveals that he grew up listening to Wood’s father, Roy Sr., on the radio in Chicago. (Wood tells me his father loaned Don Cornelius the money to shoot the pilot for Soul Train, but instead of accepting an offer to become a producer on the show, he demanded the money back.) True to Bruce Bruce’s lesson, Wood took pictures with the staff, bought popcorn, and invited everyone to the show that night.
Later, just before showtime, I watched him take a call from the comedian Ms. Pat and walk her through a tense situation, his calm demeanor never wavering. Many of his openers are black female comedians. “Roy really is like the Black Uncle of Comedy,” Paris Sashay told me over a Casamigos pineapple cocktail at The Bishop Bar. “Roy is giving so many people opportunities that the industry might not give them. He’s genuine. He really cares and tries to help people out.”
Wood’s final chance to fine-tune comes at The Comedy Fort, a new venue in Fort Collins, Colorado. One way to determine whether a headlining set is going well is by counting the applause breaks. Roy get fourteen in the first twenty minutes of his set. The special seems dialed in.
Finally, it’s time for the first official show, at Colorado’s Gothic Theatre. There’s thunderous applause as Roy makes it out onstage. He performs the hour he perfected over a litany of shows across various states. Some comics take their time in grabbing the audience. Roy has the crowd in hysterics within seconds. The tapings go without a hitch. Although he calls it imperfect, you’d be hard-pressed to find an audience member who’d agree. Countless comedians, most with serious credits, are quick to gush over the new special. Whether the mainstream will catch on this time remains an open question. But after twenty-three years of performing, this titan from Birmingham is still growing, still developing, and still making audiences laugh. Imperfect Messenger isn’t perfect—that much is clear from the title. But Wood won’t aim for anything less.