Stand-up comedian and Daily Show correspondent Roy Wood Jr. hits the road before his 2023 White House Correspondents’ Dinner host gig

Roy Wood Jr

One of the first things that I remembered when eternally perturbed, always put-upon Daily Show correspondent Roy Wood Jr. set his gig as the host, roaster and entertainer for 2023’s White House Correspondents’ Dinner was how I had spoken to the stand-up comedian during one of his last tours. And when Wood Jr. appears at the Washington Hilton on April 29, the job comes with the comedian’s very real chops as a one-time news Florida journalist.

“Roy Wood Jr. brings a journalistic eye to his comedy. He’s hilarious — but also makes sure his audiences are thinking as they laugh,” Tamara Keith, WHCA president and White House correspondent for NPR told the Hollywood Reporter. “My aim with this year’s dinner is to lift up the importance of a free and independent press to a functioning democracy, so I am thrilled to be able to feature a comedian who gets what journalism is all about.”

Wood Jr. told the Hollywood Reporter at the top of February, 2023, “It’s an honor to be a part of a long-running tradition of celebrating those members of the media, who work so hard to uncover the truth, and hold our government accountable. It will be a great night that will go down in the history books, or not, depending on which state you live in.”

In addition to The Daily Show and his brand-new stand-up special, Imperfect Messenger, on Paramount+, Wood Jr. is currently on tour with upcoming gigs at PunchLine Philadelphia, (March 3-4), at Long Island, NY’s Tiles Center for the Performing Arts in conversation with Trevor Noah (March 7), and Tempe, AZ’s Tempe Improv Center (March 24 and 25).

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Though our interview occurred a few years ago, Wood Jr.’s new White House Correspondents gig and this fireside chat oddly still sound right on time.

A.D. Amorosi: You were in Florida, working as a morning news reporter for Hot 105.7 before moving into comedy. How did executing real news without a humorous bent – being a reporter – figure into your work on The Daily Show?

Roy Wood Jr.: There is a degree of fact-checking that you must do, and real news muscles that get worked at The Daily Show. Thankfully, before I got to Birmingham, Al. and writing for The Buckwild Morning Show, I had shaved off the uptight journalistic behaviors and traded them in for gossip stuff. But, [some of it] definitely stuck with me. There’s definitely a level of concern at The Daily Show in getting all the facts lined up.

A.D. Amorosi: You work with like-minded comedian-correspondents at The Daily Show and definitely have made your place there. How quickly did you find your own voice there?

Roy Wood Jr..: As a correspondent there, our responsibility is to bring and show off your own voice, style and opinions. No one else can touch that. It’s been fun to be able to take a segment you pitch – or have one assigned you – that might not be structurally perfect at its inception. With time, you analyze different angles. You shape an outlook. Somebody may pitch me a story about a grocery store and lead with the bananas. I might look at it though, and see that story in the oranges and go from there. It’s still a story about the produce department, but maybe there are different relationships to consider now that we’re leading with the oranges. Maybe we can include the prunes and lettuce. Maybe the apples don’t approve of the bananas’ behavior.

A.D. Amorosi: You first got famous for your prank phone call CDs such as “My Momma Made Me Wear This.” How did that happen in the first place?

Roy Wood Jr.: That was all about me trying to keep a job, dude (laughs). I began making calls when I started radio in Birmingham because I was told that my predecessor, Rickey Smiley, who is now nationally syndicated, made that his thing. The station dug that. So, I started doing them in order to keep my job. This was before YouTube, so going viral meant people e-mailed your stuff around. So, I put all of my prank phone calls on my website. Now, because the station’s webmaster at that time was really lazy, he wouldn’t put them up on their station’s website. So, I put them on mine. Suddenly, I started getting e-mails from Iowa and Wyoming and across the South. These people weren’t listening to the station. They heard of them from my website and shared them via e-mail. From that point forward, we were off to the races…All because of a lazy webmaster.

A.D. Amorosi: So, how did stand-up comedy become your thing, and how soon after you started doing live gigs did you find a signature?

Roy Wood Jr.: 1998. I was doing hard news and making a transition to radio sidekick around the same time. Now, that station had a comedian who was a school teacher, so he could only tell jokes until 8 a.m. when he had to leave for school. So, from 8 [a.m.] to 10 [a.m.] I did news and cracked jokes. After a few months of that, in the morning, I figured, why not take it to it to the stage? But I don’t believe that I captured the essence of who I am until 2006. It took a minute. I was burned out on radio. I was annoyed and perturbed at, well, life. Things weren’t going as quickly as I wanted them to. So, I was frustrated. My stand-up reflected that. By the time I did Letterman in 2006…I had a lot more to be annoyed about.

A.D. Amorosi: You are all over the Comedy Central schedule, as well as having more than a few stand-up comedy specials to your name since The Daily Show gig started. What’s so frustrating to you now?

Roy Wood Jr.: I hate that people look at the big picture and rarely the small picture. I believe there is, to some degree, such a focus on politics on a national level that we miss the local level. We should be more open to changing lives and creating opportunities at that local level. We’re so bogged down by national outrage that too many things fall by the wayside.

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A.D. Amorosi: Have you had enough yet of having to report every bit of goes on in Washington, D.C. on a minute-to-minute basis or is that vein too rich to not mine?

Roy Wood Jr.: I don’t believe there is any one person, topic or trend worth the suffering that happens in the real world – because of their actions – that I would exchange for a laugh. I would always prefer not to discuss good people being deported. I would rather go back to making fun of how high Obama wore his pants than another word about this administration. Plus, a more boring time period – or one at least a little action packed than this – might force comedians to make up new material that’s relevant and hits hard.

    • A.D. Amarosi's Headshot

      A.D. Amorosi is an award-winning journalist who, along with working for the Philadelphia Weekly, writes regularly for Variety, Jazz Times, Flood and Wax Poetics, and hosts and co-produces his own SoundCloud-charting radio show, Theater in the Round for Pacifica National Public Radio station WPPM 106.5 FM and WPPM.org.

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