Roy Wood Jr. Thinks Your Career Is a Joke

After years of making us laugh at our pain, the most likable man in comedy focuses on the most painful thing of all: our jobs

Roy Wood Jr. is the kind of guy who makes everyone comfortable. He has a talent for making strangers feel as if they grew up with him on his street in Birmingham, Alabama. Even if you have dissimilar viewpoints and values, you’d still want to sit and have a beer with him. It’s part of how Wood has been able to spend his career tackling difficult topics. It’s also why the 42-year-old comedian has remained busy, even in the midst of a pandemic.

In addition to being a correspondent on The Daily Show, Wood recently launched Roy’s Job Fair, a new podcast that explores the pain and comedy in looking for, finding, and keeping a job. Wood has also gotten back to hitting the road to prepare for his third Comedy Central special; his previous, No One Loves You, is the channel’s highest-rated stand-up special since 2017.

Roy Wood Jr. got comfortable with LEVEL, opening up about how Covid-19 has affected the stand-up comedy scene, the inspiration behind his professional life–focused podcast, and how to find humor in touchy topics.

LEVEL: With Covid-19 vaccines making the rounds and social distancing mandates loosening, are you excited to get back to touring?

Roy Wood Jr.: I’m waiting for other comedians to hit the road first—end of spring, maybe summer. I’ll probably do some shows in the city; New York seems to have a grasp on the situation. When I’m booking road dates, I have to check against Covid protocols, restrictions, and the infection rate. I’ve never had to do more homework in my life.

I was a little surprised to see you had a stop in Austin.

Yeah, man, I’m supposed to be going to Austin in June. That might be one where I go straight to the venue and right back to my hotel room — no hanging out.

Is there anything you can’t wait to do when we climb out of all of this?

Honestly, I’m not sure that I miss anything right now, which is odd. You know, as much as I love stand-up comedy and being on the road, I’ve had so much more fun writing scripts for shows. I love the challenge of stand-up, which is why I’ve already signed up to do [another] special in the midst of a pandemic. And that’s gotta air this year.

How challenging is that during a pandemic?

I have a great deal of material that I was working on before the shutdown, but I need to get back on stage and see if, tonally, audiences are still in that space and talking about those topics.

We saw Kevin Hart take his stab at it with his special.

Yeah, Kev did the joint from his house.

I still can’t believe that’s his house.

If that’s Kevin’s house, then I definitely did something wrong with my life. [Laughs]

You got the sense that he was working on his rhythm as well.

There’s a degree of expiration with stand-up. Right now, I’m really interested in how jokes develop in a time where folks are quicker to scrutinize jokes in their infancy, coupled with the complications of Covid restrictions creating environments that aren’t conducive to laughing.

How so?

You perform in a room with a capacity of 400, which is cool, but the room is so spread out that it’s hard to get a sense of whether or not the jokes are really landing. It makes it hard to know what these jokes will do by the time they get to television.

You did a show a while back where you did your set in a room separate from the audience. At one point, that felt like it might be the future of comedy.

Yeah, “7 Minutes in Purgatory.” I don’t think stand-up will be that crazy. I did a couple Zoom shows that felt similar to that format, because the audiences are muted, which feels odd. I didn’t mind, because it was a space to get my rhythm back, but you still don’t know if people are laughing and what adjustments you need to make on the fly, because you’re not with a live audience. It felt more like a focus group.

Between the inability to read the room and people being more sensitive to particular content, are you afraid of saying the wrong thing to the wrong crowd and it going sideways?

I’m afraid, but the reward is still worth it. Comedy is interesting, because it’s the only product made in front of the consumer. If you went to a restaurant and the chef was cooking practice meals, you would say, “This place sucks.” So we wait for the chef to develop a menu. That’s why we have test kitchens. There are no test kitchens in comedy.

A lot of people are pivoting in their careers; I wondered if there was a way to make it funny.

We’ve been watching you on The Daily Show for six years now. Folks like you, Trevor Noah, and John Oliver have mastered the role of comedic journalist. How hard is it to ride the line between the story and the joke?

The line between the story and the joke is easy. The line between the pain and the joke? That’s hard. You have to make sure you know where the pain lies and make sure you aren’t clowning that part. The comedy comes in seeking the solution and looking at the folks who are blocking the solution.

Is that the difference between punching up and punching down?

Yeah, you look at a guy like [Georgia state representative] Carl Gilliard, who is fighting to end the citizen’s arrest law that cost Ahmaud Arbery his life. We talked about the law itself and its origins; we didn’t make it about the Arbery case. The segment was about how a law this ridiculous is still on the books. That’s how we find the joke. It’s about “how did this happen,” not the actual happening. Especially as the Black correspondent, I understand that we already know this is not new information for Black people. For us, it’s about the exploration into the causation and looking at a solution.

Where did you get the idea for Roy’s Job Fair?

When unemployment hit 30 million, a buddy of mine from Birmingham called me. He was out of work. You have so many people who have these jobs where you need to be outside. You have to go out to do the things. Somebody told him he could get a tech job and didn’t need a degree in tech, so he taught himself how to code. I thought it was interesting. A lot of people are pivoting in their careers; I wondered if there was a way to make it funny.

The hunt to provide for you and your family is as much a shared experience as food and relationships. No matter who you are, from the time you make your first dollar to the day you retire, you are either trying to get a job or you have one and are looking for a better one. The podcast will never be the want ads, but I think it could be a place where people commune, which is why I wanted to take live calls.

What’s it been like taking calls and talking to folks directly?

It’s the one thing I miss about doing radio. Being on The Daily Show, you know what people are going through, but you’re not always talking to them. But now, if you know people are going through something, well fuck it, let’s talk to them. Let’s laugh about work.

I said it in the promo, work is like sex: You either get it regularly or you’re trying to get it.

James Baldwin said something similar. He said money is like sex in that when you got it, you don’t think about it, and when you’re not getting it, that’s all you think about.

[Laughs] That’s a thousand percent true.

The past year has seen a big push to get Black folks more opportunities and to put us in spaces where we have been overlooked. Being as busy as you are, have you noticed the difference?

Here’s my issue with this surge in Black inclusion in entertainment: There’s still a huge gap when it comes to funding Black companies. Do our stories need to be told? Of course. But we also need money to tell new stories. That requires funding. I believe that part is still denied to us. But in the short term, yeah, it’s great that all this Black stuff is getting made and all these opportunities are opening up, because the other thing that it’s doing is getting Black staffs experience to go out and get jobs elsewhere.

Last thing: Rate Trevor Noah’s afro on a scale from one to 10.

[Laughs] I’ll give it a seven, but he got it edged up for the Grammys like a chump. He should have kept it African.

Writer (duh). Bylines @LevelMag @thegrio @NBCBLK. Co-creator of the Good Talk Podcast Network. Don’t forget to add me to your Medium email list!

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