On the Road with Roy Wood Jr.

“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.”

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