The joke was uniquely Wood. His cracks aren’t as caustic as Chris Rock’s or as inventive as Dave Chappelle’s. But Wood, best known for his work as a correspondent on “The Daily Show With Trevor Noah,” might be the closest thing we have now to Dick Gregory, the civil rights-era satirist who died in 2017.
Wood is one of the country’s foremost comic voices on social issues, especially those affecting African-Americans. There were points in his life when this career would not have seemed possible. But how far he’s come is evident in his new Comedy Central special, “Roy Wood Jr.: No One Loves You,” having its premiere Friday, and at many live dates a year. Wood’s goal isn’t just to make audiences laugh. “I wish I had that freedom,” he said. Instead, he wants them thinking as well about the African-American experience.
Wood met Gregory, one of his comedy heroes, in 2011 and asked him why, later in life, Gregory was still performing. He answered: “The fight for freedom is out there — it ain’t at my house.”
The conversation changed Wood’s career. Almost overnight, he transformed himself from a wry observational comic to one who felt his material had to have higher stakes. “The stuff that mattered to him,” Wood said, “these are the things that I obsess and think about.”
Wood, 40, seems perpetually exasperated, which is apparent from his stand-up. The morning we met, he was wearing a “You’re not listening” T-shirt, a reference to the cue cards football player Malcolm Jenkins held up to express frustration about the discussion surrounding players kneeling during the national anthem. In his special, Wood jokes that the national anthem controversy is especially absurd because the tune of “The Star-Spangled Banner” is based on a British song: “Now, you’re running around telling stolen people in a stolen land that they should stand for a stolen song?”
If Wood’s comedy was influenced by Gregory, his worldview came from his father, Roy Wood Sr., a civil rights activist and radio commentator in Birmingham, Alabama. He was one of the first hires at the National Black Network, an African-American news syndicate, and he and his son often watched “60 Minutes” together, planting the seeds of Wood’s topical approach today.
“My dad was a very opinionated man,” Wood said. “He was constantly analyzing the world and how black people should move in it.”
Wood said he didn’t know whether his father, who died of prostate cancer when he was 16, would approve of his career. “I was in a dunk tank in eighth grade,” Wood recalled, with a chuckle. “He didn’t like me making a fool of myself. He just kept saying, ‘You’re nobody’s monkey.'”
His mother, Joyce Dugan-Wood, a college administrator, said she wasn’t sure either. “What I think I’m afraid of is that his dad was very serious when it came to social issues,” she said. “I would like to think that he would be proud.”
Wood might have taken a different path if not for his mother’s purchase of a basketball hoop. Raised in the rough West End neighborhood of Birmingham, he said he faced constant pressure to join a gang. In his telling, Dugan-Wood didn’t want her son to go to the courts, where shootings would occur between rival factions. To keep him close, she put up a hoop in a driveway surrounded by trees.
“Not only do I have the best goal in West Birmingham, I have the only shaded basketball court in Alabama in the summer,” Wood said. “If you build it, they will come.”
Gang members would leave their guns at home and come play, Wood said. If anybody created trouble, they wouldn’t be allowed back. The hoop, Wood said, “saved my ass.”
It was a much more serious brush with the wrong side of the law that led Wood to comedy. A student at Florida A&M; University, he stole credit cards while working at the post office and used them to buy jeans. “There was no real agenda other than making money and looking fly,” Wood said, adding, “Most crime comes with little logic.”
He was arrested in his junior year. Suspended from college and facing incarceration, “I spent every week on the Greyhound bus, riding around the South just doing standup to deal with the depression of knowing I had to go to prison,” Wood said.
Except he didn’t end up behind bars.
A judge took pity and sentenced him to probation. His probation officer encouraged him to keep doing comedy — so Wood fit in shows around classes. A few years after graduating in 2001, Wood sent him one of his comedy albums as a thank you. The officer returned it, saying he couldn’t accept gifts. It was the last time they communicated. But the officer’s influence inspired Wood to pitch Comedy Central on a pilot, now in development, about two probation officers in the South.
“Getting arrested was the best thing that ever happened to me because it literally gave me the shock to the system,” Wood said.
After working as a radio host in Birmingham following college and continuing to do standup, Wood received his big break on “Late Show With David Letterman” in 2006. In addition to relentless touring, high-profile gigs followed, including “Last Comic Standing,” several late-night appearances and television acting jobs.
In 2015, Wood landed an audition for “The Daily Show” thanks to the recommendation of another comic, Neal Brennan, who described Wood in an interview as “weirdly sophisticated and working class.”
Wood had actually auditioned before — in 2008, when Jon Stewart was the host — but he bombed. (Wyatt Cenac got the job.) In 2015, things went differently. Noah, who was preparing to take over for Stewart, saw Wood do a set at the Cellar the night before Wood’s audition.
“The job was his before he left the stage,” Noah said by email. “The audition the next day was just a formality.”
Wood appeared on the show the night Noah debuted as host.
“Maybe it’s because he’s Southern, but there’s an authenticity to his point of view that isn’t shaped by popular opinion,” Noah said. “He questions everything and he challenges the ideas so many of us have accepted as normal.”
Now, Wood, the father of a 2-year-old, sees himself as a more mature comedian than when he first auditioned for “The Daily Show,” one with a more distinct point of view who thinks about what he would tell his child when he is older.
“I have to talk to my son about any of the dangers of the world and how to carry himself, not just with authorities but making sure that he’s a decent person around women as well,” he said. “The rules are still being rewritten. But as they’re rewritten, it’s my job to keep updating it.”
At the Olive Tree Cafe next to the Cellar, Wood reflected on a wall of comedians’ photos after finishing his set. The Cellar is a Shangri-La of sorts for standups, and, in a sign that he’d made it, Wood’s picture was hung there last year.
Near that picture is one of Louis C.K., who has been performing again after admitting to sexual misconduct with several women. “They tell you that when you get in trouble you find out who your real friends are,” Louis C.K. joked in one of his comeback sets. “It’s black people, it turns out. They’ll stick by you.”
It might surprise some that Wood wasn’t insulted by the crack, as some other African-Americans were.
“Black people have been at the bottom before,” said Wood, who is not friends with Louis C.K. “So when someone is going through adversity, who’s more qualified to coach you through it than someone whose entire existence has probably been adversity?” He added that he didn’t have an issue with Louis C.K. being onstage again.
“As a man whose life has been a constant run of people giving him second chances,” Wood said, “I’m not here to judge anybody on who’s coming to ask for theirs.”
This article originally appeared in The New York Times.