How Roy Wood Jr. Became the Latest ‘Daily Show’ Breakout Star

“Roy, what can you tell us about these new developments?”
“I can tell you I don’t give a shit.”

From his first appearance on-screen in September 2015, new Daily Show correspondent Roy Wood Jr. came across like a seasoned smartass who had been doing the job for years. Clad in a gray suit and sporting a cockeyed, little smirk, the 37-year-old stand-up comic argued the potential colonization of Mars meant nothing to a black man in America. (“Brother can’t catch a cab, you think he can catch a spaceship?”) When TDS‘ unruffled new host Trevor Noah giggled, Wood put him in his place: “You’ve only had the Daily Show for one commercial break, these white folks ain’t decided if they like you yet!” With an easy Southern charm and an artfully crafted sense of frustration, he immediately stole the show. It took the Steves — Carell and Colbert — months to figure out their TDS personas, but Wood was just suddenly there, an exasperated everyman who saw the big picture in a way that no one else was able to.

This moment, a seeming sort of overnight success, was 17 years in the making. Wood’s comedy career started, ironically, in Journalism school. At the age of 19, while delivering impromptu speeches in a public speaking class at Florida A&M, he became frustrated (and nearly flunked) when classmates found it easier to laugh at him than take him seriously. It wasn’t long before he was hitting up open mic nights, and then a loose constellation of comedy clubs in cities across the South and the Midwest. Wood’s comedy habits inhibited his ability to land internships and steady jobs, so after graduating he moved back in with his mother in his hometown of Birmingham, Alabama, and kept touring.

“I always hear these stories about groups of comics [from big cities] like, Oh yeah, we came up together,” says Wood. “I don’t have those memories. I didn’t have those friends. Most of the people I started with are either dead or they quit.” Instead of relying on a support system, Wood steadied himself and set goals: He determined to perform at a new venue in a different city each month, then worked to get booked in comedy festivals or nab certain TV credits.

“If everybody’s thinking apples, I’m going to talk about broccoli. I’m not even going to write about oranges, because there’s at least three people who wrote about oranges.”

“The thing that kept me going was the next joke,” says Wood. “And every year, no matter where I was in the comedy game, there was an opportunity to do what I call ‘skipping a level.'” To wit: The local hip-hop station 95.7 JAMZ wouldn’t consider him to replace departing comedian Rickey Smiley. When they sponsored a visit from D.L. Hughley, Wood told the club owner that he worked for JAMZ and was meant to open for the headliner; the up-and-comer then encouraged the radio station’s reps to see him perform at their own event. His 10 minutes killed — and as he walked off stage, the morning-show DJ offered him the job on the spot.

His creative thinking paid off once he was on the air as well: He started doing prank phone calls during his affiliation with JAMZ, and despite the fact he “didn’t want to do that shit,” he became an expert at taunting unwitting Birminghamians about their parenting skills or unpaid bills. Once fans began posting his calls to YouTube, he was able to book more stage time after convincing out-of-town stations to play his “syndicated” bits and then hitting up local club owners.

Wood’s stand-up bits are often gripes about life’s little annoyances, e.g. the high price of soda at the movies or ridiculous ATM fees. Still, he doesn’t mind pushing buttons when the time is right. In his 2013 album Things I Think, I Think, he talks about the “hazing process in America” for minorities, telling a slightly uncomfortable crowd that “if you’re a minority and you want some rights, you’ve got to go pick some shit, damn it.” While Wood is sensitive to audience response, he refuses to pander. “If you’re uncomfortable, that’s your problem,” he says. “If everybody stopped the moment the first person in the crowd went, ‘Hoooo,’ comedy would be bland as that old tea bag that’s brewed for the fifth time.”

The comedian was also amassing a number of television appearances along the way, including a Late Night with David Letterman spot, four visits to Conan and a third place finish on Last Comic Standing. He spent five years auditioning and doing sets in L.A. before being cast on Vince Vaughn-produced TBS sitcom Sullivan and Son, which lasted three seasons. When he got a call to tryout for The Daily Show, he’d just found out that the ABC pilot he costarred in with Whoopi Goldberg hadn’t been picked up. In other words, the prospect of TDS was exciting but “psychologically, it was just another audition.”

The desk piece he wrote for his tryout, an argument about why the confederate flag should not be abolished until there’s a better way to identify racists, exhibited the same off-kilter thinking as his stand-up. “If everybody’s thinking apples, I’m going to talk about broccoli,” says Wood. “I’m not even going to write about oranges, because there’s at least three people who wrote about oranges.” The producers and its new host picked up on Wood’s fresh point-of-view immediately. “Roy has a great way of seeing the other side of any conversation, which is always a great mindset for a comedic take,” says Trevor Noah. “And script or no script, I know we can find funny. Even in his most serious moments, there’s a joke in his eyes.”

When Wood walked into the Daily Show office for the first time, he realized “everything [I’ve] done is just an internship to prepare [me] for this moment.” Thankfully, he brought a lot of transferrable skills with him: The stand-up bolstered his stage presence; the prank-call experience kept him cool while managing sensitive interviewees; previous on-camera work eliminated his jitters; and a journalism degree helped him to understand when and how to look behind an issue. “I still watch news, but my focus isn’t on what was said, it’s what people are saying about what was said,” says Wood. “It helps me figure out the psyche of America.”

A piece following a pair of elderly Republican voters invoked their humanity and a sense of hope in the electoral process, and a story about gambling on the presidential election was a convincing endorsement for the practice. Though he groused about having to address issues of race in a piece about the porn industry, Wood recognizes both the opportunity and responsibility there. “Unfortunately, we are at a time in this country where race is the top of the discussion,” says Wood. “I’m doing a disservice to the black community if I’m not addressing race every now and again.”

He still tours clubs on the weekend, and wherever the comic moves, he wallpapers his office with a vast collection of postcards  — one picked up in every city in which he’s performed. It’s an impressive visual aid that helps Wood all that he has accomplished in 17 years. “There are nights where it’s very stressful and I can look up and think, Oh, I’ve come a long way, I should probably keep pressing on,” says Wood. Then, with a smile, he adds, “Of course, once you get to a certain mile marker, you don’t have a choice.”