Roy Wood Jr. is an Emmy-nominated comedian, writer, producer, actor, radio personality, and podcaster known for his stand-up comedy and work as a correspondent on Comedy Central’s The Daily Show. He joins the Design Matters Live Tour to discuss his career, entertaining millions across the stage, television, and radio.
Debbie Millman:
So, Roy, I know you were born in New York.
Roy Wood Jr.:
Yes.
Debbie Millman:
But you claim Birmingham, Alabama as home.
Roy Wood Jr.:
Yeah. My father was in journalism, and so he worked for WCBS at the time. And then as soon as I was born, he got another job. You know journalism, you just bounce around.
Debbie Millman:
You go where the job is.
Roy Wood Jr.:
So we were in Memphis till I was in the third grade and then Birmingham after that. I feel like wherever, first bully, first kiss, high school diploma. If you got two out of three in the same city, that’s where you’re from. That’s my metric. I know that’s not an official statistic.
Debbie Millman:
No, that’s actually a good metric. That means I’m from where I was born, Omaha, Nebraska. Not great. So how did Birmingham shape you, especially if you had two out of three of those milestones there?
Roy Wood Jr.:
I think Birmingham shaped me. It’s an interesting place because it’s essentially 75% Black. Just Black American Black. I don’t mean immigrants or any other type of Black diaspora, just regular ass, cheese grit, Black. So this idea of racism and all of that was… I’m not saying that it wasn’t foreign. We were taught it. You’re educated about it. And I had two parents. My father was a civil rights journalist and my mother was a college educator. Eventually spent the rest of her time at a HBCU. So the idea of the world is terrible, you really didn’t get that unless you were over the mountain in the suburb shopping and you got followed around the store or you played a white school out in the county for whatever sports you played and you get called the N word or whatever in the middle of the game and the ref or that they didn’t hear it.
But day in, day out, I was around Black people. Every school I went to was predominantly Black. I had mostly Black educators. So Black barbershop. I got bit by a Black dog. So this idea of how terrible the world is, I was prepared for it, but I only got it in sneak previews. Like the idea of diversity and what we have now, I didn’t have a Latino classmate until the seventh grade and Asian until the sixth grade. Just didn’t know them, didn’t meet them, they just weren’t around. And then in high school I went to an alternative high school, so it was half white, half Black, and that’s where you get into the foreign exchange students and all of that type of stuff.
Something that’s so commonplace in most cities like in Alabama, there will be a conversation before like, “Hey guys, there’s going to be a Russian joining us today.”
Debbie Millman:
Something different.
Roy Wood Jr.:
“This person is from Nepal. Do you know where that is?” And we’re like, “Nope.” So it was very Black. It was very positive though.
Debbie Millman:
Do you think that positive influence in seeing Black as the center of your universe, did that help shape your comedy in the ways in which you tend to have a less cynical outlook than a lot of comedians?
Roy Wood Jr.:
Growing up in Birmingham for sure made me optimistic about what the world could be because I also grew up around people that were trying to change the city and make the city a better place. So that was probably a big part of it. For me, I’d say the biggest influence was when I started doing morning radio. So I leave Birmingham, I graduate high school, I go to Florida A&M, I get a degree in broadcast. I come back to Birmingham at 95.7 Jamz as an intern, which was the same station that Ricky Smiley started on, which is a huge, huge influence just in Black radio.
That second generation, Tom Joiner, he runs with Steve Harvey. So it was a big deal to be Black and be on the Blackest station in a Black ass city. And so what I learned from intern up to host over that decade was how many different ways people in the community were trying to make the city a better place. So this idea of what Alabama is in the perception of Alabama, I know a completely different place. We were the community, we were the number one station, but we were also the community station. So we legit showed up and did good shit.
We gave away homes and cars and there was a tornado in Tuscaloosa to Birmingham in 2010, 2011 if you want to Google it. Killed 50 people. Our station was on location before the Red Cross helping people. And so the idea of seeing white people and Black people coming together, I didn’t seen it, man. I hadn’t seen it on a regular basis. So when people go, “Oh, this…” So when you take that perspective and then you look at the national racial division that we have in this country, and you look at a lot of how angry both sides can be and how everybody has a degree of hopelessness, I just don’t have that because I’ve seen something different. I know why you’re mad and I agree it is messed up, but I also believe that there are people, we just have to find them and inspire them and get them the tools and the assets they need so that they can go out and change stuff.
Debbie Millman:
How do you communicate to people what you’ve seen and that you have seen that people can work together across divisions?
Roy Wood Jr.:
I just have to be that and then let them find out I’m from Alabama, then they be up off of it. “Really you’re from Alabama? You don’t sound like you’re from Alabama.” So I just try to be a good person. You can be an ambassador, but at the end of the day it’s just about trying to shine a light. You take a story like the Alabama Supreme Court gerrymandering, whatever. They drew up all of the districts. They kept redrawing them after Doug Jones beat the… What’s the boy with the cowboy head? Roy Moore. After Doug Jones-
Debbie Millman:
Oh, yeah. The guy who slept with 16-year-olds.
Roy Wood Jr.:
Beat the guy. Yeah, the guy who sometimes goes to the mall on Saturdays to see what’s cracking. And so after Doug Jones beat him, they redrew the districts in a way so that there wouldn’t be another Doug Jones who was a blue senator. And people fought and fought, and fought to get that to the Supreme Court and they won. Those people are also there. But the story that would get the bigger attention is the original story, which is, “Why would y’all elect Tommy Tuberville? Can you believe that, man? Alabama is so stupid. He don’t even live in Alabama.” We tried to not vote for him.
So the conversations about change just don’t happen as fast in Alabama because the bad news comes out at a much quicker turn and burn. I mean, you look at Georgia. Georgia really ain’t nothing but Alabama probably 20, 30 years in the future in terms of progressiveness. And Georgia isn’t seen as a hopeless place. But if you dig into crates and pull up some of the policies that were getting passed in the state of Georgia 30 years ago, it’s pretty bad. You might’ve had that same hopelessness 30 years ago. That makes sense.
Roy Wood Jr.:
Yeah.
Debbie Millman:
A lot of people say they’re funny and think they’re funny and perhaps are not.
Roy Wood Jr.:
I would never say that I’m funny.
Debbie Millman:
I find you funny.
Roy Wood Jr.:
I’m glad people laugh.
Debbie Millman:
When did you first know you were funny or at least believe that you could take your gift for the gab out and put it in front of people?
Roy Wood Jr.:
Sports. Because I mean, again, having… Between my two parents, there’s five degrees, five college degrees, so there was no cutting up in class and not getting your education. So I wasn’t really a class clown. For the most part, I was pretty straightforward. Even if I wasn’t making good grades, more often than not, it was just because I was just distracted, but I wasn’t a bad child. But on the baseball field, you could be a totally different person. After school, you can be something that you aren’t and then you’re around like-minded individuals. There’s a bond and a kinship that comes with sports. So I rode the bench a lot. I was not good. I was good enough to make the team, but never good enough to play-
Debbie Millman:
Get on the field?
Roy Wood Jr.:
… regularly. Because that shit stops at 12 like everybody gets a turn. That’s little league. Everybody plays. And then once you hit ninth grade JV, “Sit your ass over there and we’ll let you know.” And so when it came time to heckle the other team… And keep in mind, this is Birmingham. At the time 10 Black high schools. It’s down in consolidated, but at that time it’s 10 predominantly Black high schools. So the bulk of your schedule is Black kids playing other Black kids from other sides of town. And we would go to work, we would talk shit. We would crack. We would Jones, whatever you call it. And that became my job. That’s how I contributed. I’m not going to play, but that kid right there, I’m going to break his soul.
Debbie Millman:
Wow. Before Beyonce even.
Roy Wood Jr.:
We were dirty. We would watch the car that you got dropped off in.
Debbie Millman:
Oh, no.
Roy Wood Jr.:
If you got dropped off in a raggedy ass car, I’m on you. And so that became the place where humor was a bit of a weapon. And so now, because I’m funny at the baseball field, at school, I’m cool. I’m not getting picked on or bothered or whatever. I was never the coolest kid, but I definitely could move between different circles because of sports because all of my teammates hung in different social circles. So for as long as there was one person in that circle that was on the baseball team, I was accepted within that circle.
So it kind of made me a man of many countries where I could kind of just bounce around. I could hang with the golfs, I could hang with the gang bangers, I could hang with the nerds. I could be in chess club one minute and then be outside skipping school, going to McDonald’s in fifth period.
Debbie Millman:
Do you think that was a sort of foreshadowing of the way that your comedy appeals to a really wide audience, that ability to cut across different lifestyles?
Roy Wood Jr.:
Yeah. But I would say for sure that’s probably where on some superhero Ironman in the cave building, the first suit, Batman Begins type shit. Ironman came out too long ago. I had to add.
Debbie Millman:
No, I know what you’re talking about.
Roy Wood Jr.:
I had to add Batman Begins on the bad shit.
Debbie Millman:
When he was using all those jankity tools in the cave.
Roy Wood Jr.:
They called the second one. Okay. That was the beginnings of it. But I would say where I really cut my teeth and having to learn how to entertain different demographics was in college. I was 19 when I started standup. I was a server at Golden Corral. It’s not bad.
Debbie Millman:
The little rolls are really quite delicious.
Roy Wood Jr.:
Don’t go there on a date. It’s not romantic. That’s where you go once you got them, once y’all married.
Debbie Millman:
Once you’re comfortable and you can wear your loose pants like, “Baby, we’re going to Corral. Get your sweatpants.”
Roy Wood Jr.:
So at Golden Corral, as a server, I need to connect with you in 30 seconds if I have any shot of getting a tip. The moment you sit down, I believe that is when a customer decides what your tip is going to be. For as long as you establish something great and you don’t fuck it up the rest of the run, you’re going to get a good tip. I don’t think you can start off stale and slowly lighten up because when you’re interacting with a customer in a restaurant, each interaction is shorter after the initial interaction.
So I don’t have as much time. I’ve got 30 seconds up top. “What do you want to drink? I’ll go get your drinks. Here’s some plates. Welcome to… Then over here is that. The bread is over there, over there.” And I need a joke between each of those sentences because after that I’m just taking dishes and refilling drinks. I don’t have any time. So what is a joke? How can I connect in 30 seconds? And then what is that joke that I can use at the next table over who didn’t even hear me talking to you? And those are two different demographics.
Debbie Millman:
Yes.
Roy Wood Jr.:
So what is the joke that an old couple will laugh at and that five teenagers will laugh at even though only three of them paid for the buffet. And then with Florida State being in Tallahassee as well, game day was very important. So I would research. I would read up on the teams, whatever team was coming to town, the visiting team, I would read up. I’d find a game capsule online and learn a little bit about the team and then just ask the people at the table about a player or whatever.
And so what I figured out is if you can find out the things that people care about most and get them talking about it, I don’t have to say shit. So it became a sociology thing where what I found out was essentially food, relationships, money or entertainment. No matter who you are, one of those four things excites you. You have a favorite food, you have a favorite show or a sport. You’re either in love or you want to be in love. You’re figuring out a way to make money. That is the same for every American that walks this earth. Those were the four things that I always used. And once I started doing standup in the south, it was actually a little more circumstantial.
Now, high school helped, Golden Corral helped, but the circumstances of it was when I started doing standup to do comedy weekly to make enough money to pay bills, you’re performing in front of a different demographic every night. So what is the 20, 30? In those days, I was only doing like 15-minute sets. What is the 15-minute set that’s going to work at a dive bar in Fort Walton Beach with a bunch of drunk college students? And the next night you’re in Biloxi and nobody in that crowd is under the age of 70. Because otherwise you have the burden of carrying two different 15 minute sets, which is too much to work, and you don’t have enough stage time to galvanize two separate 15-minute sets.
And then the next night you’re doing a show for some dope boys and they’re going to pay you in cocaine. So what are the jokes? So you start figuring out. You go, “Okay.” So a lot of my early material, it’s food, relationship, money and the entertainment. Those were the connectors. And if I gave you one of those, then I found that audiences would allow me to go into the stuff that interests me. So you just have to meet people where they are. And that’s really what I learned at Golden Corral as a server was figure out what they’re interested in first.
Give them a little bit of that. And then when you come back to the table… I call them drive-by jokes. Then when you’re doing the refills and you’re taking the plates, we’ve already established that we’re cool and we’re friends. So now I can do a weird joke or say something slick and it’ll be okay. And so it was more of a need of necessity than some deliberate… I did not start out writing material going, “I want everybody to like me.” But 10 years in the South, this is how you’re going to make your money. Because otherwise, if you put yourself in one demo box, you’re not going to make enough money.
Debbie Millman:
So when you were 19, you were arrested for stealing credit cards and staring down a stint in federal prison.
Roy Wood Jr.:
Correct.
Debbie Millman:
And young people make mistakes, but as we well know when Black people and Black men in particular make mistakes, the consequences are often far graver. Fortunately, instead of prison, you received probation. And that’s also when you started to go on the road with your comedy. How do you get from there to here and how were you able to take that second chance and make the most of it?
Roy Wood Jr.:
So for context, I was a mail sorter in the post office at the campus post office. I don’t know if you know about credit cards and college, but that’s where all the credit cards go first is to the post office. And so we got our night here. “Man, I want some jeans. Man, I just want to look good for homecoming.” All I want is some jeans. And that was the only purpose of why we were doing what we were doing was to get jeans to look good at homecoming.
Now, when you are arrested in this country, the first thing they try to do is pin every crime that has ever happened in your genre of crime on you. And so we get arrested and they show us this book of 10, 15 other people in the Tallahassee area that they’re investigating for a white collar crime. “Do you know him? We’re going to find your phone number and we’re going to trace it, and we’re going to connect you and you better admit to it.” In that moment, I was like, “Wow, they don’t even…” The idea that this was just-
Debbie Millman:
Just being kids.
Roy Wood Jr.:
… more of opportunity. I could have got a work study in the cafeteria and we wouldn’t even be talking about it. I may not even be a fucking comedian. So this idea that there are people in this country that want you gone, they want you gone, that was very, very real to me. And so I got suspended from school because of that. And during the suspension is when… And I’m very leery, leery about using the word depressed, but I was in a very bad and sad place and I thought that I had thrown my life away. And that’s what it took for me to try doing comedy.
So I started doing standup and it was the only thing that made me happy because here’s the other thing that happens when you get arrested, you lose all your friends. And when you’re the guy that’s helping everybody else get clothes, you’re the man. But when that’s cut off, nobody wants to talk to you. And then there are other people that are doing their own crime from selling weed and robbing. You just know an array of people. I literally cannot be around you, man, because I will go back to prison. I’m on probation.
So it literally changed my circle of friends. And so I started doing standup. I get back in school and I just kept doing standup. And that was 1998 till today. The only thing I can tell you, I never did standup with this idea of, “Yes forever. This is the dream.” All I knew when I started was I like doing this. I make enough money on the side. I was working 20 hours a week at Golden Corral. All I need to clear my rent every month was $500. So yeah, rent, phone, my contribution on cable and lights total, $500. So I didn’t have to… And then the other thing that happened to me where I got very, very lucky is that I got suspended from school after financial aid checks had been dispersed.
Debbie Millman:
Ah, yes, the best time of the year.
Roy Wood Jr.:
So I had a check. I was 19 years old. I had a check for $7,000 and no classes to pay for because I’m suspended from the class. So that money was essentially the front money to get me on the road, keep me in hotels. I was young, sleeping in bus stations and stuff, trying to cut corners. But that’s what I did. And it was just once I graduated from school, I was making enough money. I was making 18K doing comedy. The two journalism offers I had were 14. So I was like, “All right, I guess I’m a comedian.”
Debbie Millman:
So journalism has always been lucrative then?
Roy Wood Jr.:
Yeah, I took my 18K, I moved back to Birmingham. I worked at the radio station for free until they put me on salary, and I just never stopped doing standup. It was wild because I remember when I used to crack jokes at the baseball field, I remember distinctly when Comedy Central first became a network in the early ’90s, and all they showed was standup all day. They did not have programming. There was a time, children where there were droves of standup shows on every channel and Comedy Central would just compile the best jokes of those shows and just show that shit all day.
I remember being 14 and watching that and just being mesmerized by it and then realizing that’s what I’d wanted to do all along. I didn’t even know that my city had a comedy club because they didn’t even really advertise that much.
Debbie Millman:
I remember those days because I love standup and you could just watch hour after hour after hour. There were no TV shows, there were no reruns, there were no sort of vaguely related movies. And so you could really see what standup was about, especially in the early ’90s. You have been on the road for a very long time, and touring can be incredibly challenging for a lot of reasons. What do you get out of still going on the road and what are the pleasures really, and what are the pains of going on tour?
Roy Wood Jr.:
The pains change as you get older. The early pains was that it just wasn’t a lot of money. But in hindsight, it was the most fun I ever had. When you look back on a lot of your struggle years, it really is fun. I remember I drove 15 hours to Buffalo, New York for six minutes of stage time. I went to Detroit, there was a club in Detroit called Coco’s and I looked on their website and they do open mic on Mondays. So I drove to Detroit on a Monday just to do the open mic. What the website did not say is that it’s open mic rap night.
I’d driven 13 hours to Detroit and it was 28 rappers and me. I went up, it was terrible, but I drove. I’m going to do my time. I signed up. So those moments help mold you. Those are the skinny days. But then as you get older in terrain, I think that the safety net comes from under you a little bit more. I’m 44 now, so you need to make sure that you find an audience and have people that rock with you and enjoy what you’re doing and make sure that you’re staying on top of evolving your jokes.
So whereas it used to be, “Can I get five minutes?” Now it’s me going through my run sheets to see what jokes I did the last time I was in this market to make sure I’m not repeating material. What is the new stuff I can integrate in? What were the ticket sales? What were the metrics? What is my meta demographic on Instagram followers? It’s the stressful stuff that you never had to think about, but it’s the stuff that matters the most. So you can’t blow it off.
I’m from a generation where I looked up to comedians who still wanted to do David Letterman and Jay Leno, and do late night when those comedians should have been the ones that were looking at digital and where the game was going. They should have been looking at MySpace. In the early days of YouTube, the first year of YouTube, I had 100,000 followers. And that’s insane. There was no monetization back then though. And then YouTube also in that time, it was just a channel. You just listened to stuff. It wasn’t really a video priority website.
So I just didn’t give a fuck. I didn’t care. A hundred thousand? What does it mean? Kajillion? The email list, I don’t need to collect emails. Who cares? Said two or three stupid things on YouTube and caught a couple copyright strikes from posting shit that wasn’t mine and lost the account. And it wasn’t until like five or six years later where I was like, “Fuck, I was ahead of the curve.” And so making sure that you are looking ahead… Like in baseball… And to me, everything is baseball. So in baseball, when you hit a ball, they tell you when you run the first, the only thing you should be looking at is the base. Don’t look at anything else. Don’t look at where you hit the ball, just focus on hitting the bag and going through the bag.
And then the moment you hit first, you have to look up and see what’s happening on the rest of the field to decide to take second. When you’re headed to second base, you’re already thinking about third base. When you’re going to third, you haven’t even touched third yet, and you’re already assessing whether or not you should go home. And that’s what comedy is. Only you can’t see where you’re going, but you know you’re going somewhere. Even now as we speak, the sands of this industry are shifting.
Debbie Millman:
And how so?
Roy Wood Jr.:
The idea of whether or not an hour special is still what it was. Standup still matters. Televising still matters. Reaching people who consume it still matters. But the model that I had been sold for the past 20 years, I need to sit and put that shit under a microscope and decide whether or not that’s the way to go. When you look at someone like say a Matt Rife far more recently and Nate Jackson, these are gentlemen that have blown up and are selling four digits worth of seats per show. They don’t have Netflix specials. They don’t have an HBO Max special.
So it’s important to look at where the industry is going and how it’s evolving. And that’s the one lesson I was never taught from a single OG because I just don’t think that they knew. I mean, the game was the same for 60 years, and then it just started evolving every five to eight.
Debbie Millman:
Is it the internet and social media that is forcing the comedy game to evolve?
Roy Wood Jr.:
Yeah. Also, I think people’s attention spans their watch habits. I think the way we consume information is changing as well and I think that’s an important part of it. You could probably get as much coverage or as much hits or views or whatever ratings, whatever metric you want to use with a 90-second clip as you could. You’re better off as a comedian right now, recording yourself for an hour and chopping that into 90-second chunks.
Debbie Millman:
On TikTok?
Roy Wood Jr.:
Yeah.
Debbie Millman:
Yeah, I believe it because I have a little TikTok problem.
Roy Wood Jr.:
Or YouTube shorts. YouTube shorts is doing really well right now, and you should put your stuff on shorts because they’re prioritizing people who use shorts. And the algorithm will favor you if you post stuff on shorts instead of Instagram. That’s the stupid shit you have to know now. It can’t just be, “Well, is this Mitch McConnell joke insensitive? And should I do it or not?”
Debbie Millman:
Yes.
Roy Wood Jr.:
Also, what platform should I put it on and what time of day should I post a Mitch McConnell joke? So it’s such a moving target now. But that’s exciting. It’s exciting. I don’t say that as some sort of complaining curmudgeon. It’s just with touring that is the purest, “Yes, we fuck with you or we don’t,” that anybody could give in this day and age. Even right now in this room, the fact that you were here in this room, you left your house, that is a chore now.
Debbie Millman:
In the rain, by the way. Thank you.
Roy Wood Jr.:
Seriously, that’s a big thing. So if you can still get someone to get out of their house and drive and sit in a room and listen to you talk, then you’re doing something right. And to me, that is the most consistent and most favorable algorithm that will always be there. And so I take touring very seriously, but just in terms of how to grow it and how to make sure that you are still connecting with people who don’t watch you or don’t watch the daily show or whatever. Hell, even late night is changing.
So you just think entertainers as a whole have to start thinking of themselves as their own promotional vehicle. And if the studios and the networks want to rock with you later on, let them come. But this idea of waiting patiently to be chosen so you can find the people who will love you forever, that’s a sucker’s bet. If you’re still operating like that, knowing that you have all the power in your hand. You can edit, you can Photoshop with that, whatever you’re holding right there.
Debbie Millman:
I have brothers. It’s a Fold 5. It’s a folding phone.
Roy Wood Jr.:
It’s Android. Just say Android.
Debbie Millman:
Oh no, it’s an Android.
Roy Wood Jr.:
We don’t know the models.
Debbie Millman:
Don’t you worry.
Roy Wood Jr.:
She just pulled out an iPhone out of that pocket.
Debbie Millman:
Let’s be clear. I enjoy gadgets and I love that you can open and fold your phone and I feel like a spy whenever I do it. I’m just like…
Roy Wood Jr.:
And that matters. And that’s the type of stuff, how people consume stuff dictates how you create the stuff where tech goes, where porn goes. That’s where humor. I’m not even trying to be funny. Snapchat started out as something way different.
Debbie Millman:
It did.
Roy Wood Jr.:
Than what it eventually became.
Debbie Millman:
Actually all social media started with porn, Tumblr, Snapchat. The Google thing. There was a thing, yes.
Roy Wood Jr.:
Circles or something. I think only Etsy is the one that’s been legit the whole time. Etsy has always been straw bags. And freaking weird cushions for your chin.
Debbie Millman:
There’s so much on Etsy. It’s too much. I need someone to go through Etsy curate a selection.
Roy Wood Jr.:
I don’t know. Did Etsy start with dick pillows or something?
Debbie Millman:
Well, yes. One of the things that marks your comedy is that you tend to make a lot of cultural observations, and you can go to very interesting and sometimes challenging places. But how do you stay culturally knowledgeable? Because there is a lot of information and we are changing how we consume knowledge. So what does your cultural diet look like?
Roy Wood Jr.:
I am every other day a local paper from a random city, which is becoming tougher because local papers are dying. And most papers now are just wire reports or just some regional reporter that files a story. Like Alabama. There’s no city in Alabama that has a hard copy paper that’s delivered anymore.
Debbie Millman:
No way.
Roy Wood Jr.:
It’s dead.
Debbie Millman:
Not even Birmingham?
Roy Wood Jr.:
Not even Birmingham. And so it may be on Sundays. Fact check it, but I know Monday through Friday there is no paper. It does not exist. And the stories you find online are kind of the same ones you’ll find on the Huntsville website and the mobile and the Montgomery website. So I try to read locally to see what’s happening in other places. Now, that’s a habit that also came from my early five, six years on the road. When I would go to a new city, I wanted to find something local to talk about so I could connect with the people from the jump.
So whatever is happening in your town, I’m going to do three minutes about that upfront. Whether it’s funny or not, it’s something you’re interested in. So it’s almost free material, low key. It’s low risk material. You’re not expecting a punchline because I don’t live here and I’m just chatting about the thing. So that’s a habit that still stayed. Reddit, I try to go to a little bit. I read some national papers. Once I got The Daily Show, I stopped reading national papers because we consume so much national news that most national papers are just a day late on stuff. I already know what’s going on.
I like op-eds, and that’s the main stuff. It’s like if news happens, I go to Reddit and read about it. And it’s the same reason I still rock with YouTube. It’s the comments.
Debbie Millman:
Oh, well, yes.
Roy Wood Jr.:
I read YouTube comments. I’m like one of the few people that will just juggle dynamite for my stuff and for other people’s stuff. And so Reddit and YouTube, to me, the way I look at it is that Reddit is the more thoughtful version of stupid. Does that make sense?
Debbie Millman:
It really does. Like an elevated stupidity.
Roy Wood Jr.:
Yeah. But you explain in detailed paragraphs why you believe… Even right now as we speak right now, there was an F-35, a pilot ejected.
Debbie Millman:
Yes, that shit is missing.
Roy Wood Jr.:
The F-35 did U-turns. They just found it crashed in South Carolina in the woods. Nobody died. There’s already people going to government and Biden and the conspiracy. And what if AI took over the jet? And it was…
Debbie Millman:
Well, there is a movie about that. It’s called Stealth. It stars Josh something or other.
Roy Wood Jr.:
Yeah, Jamie Foxx is in that one. Yes, Jessica Biel. Yeah, I got the DVD.
Debbie Millman:
Yes, talent, taste. Love it.
Roy Wood Jr.:
So on YouTube, it’ll be short blast of perspectives, of differing perspectives across the political spectrum. Reddit is a more nuanced explanation of those spectrums of views. My job as a comedian and as a correspondent of The Daily Show is to talk about this from an angle you haven’t heard yet. So I have to know, I choose to know what is everybody else already saying about the thing? And that’s something I got to give Trevor Noah props to, because I kind of stole that from Trevor because stuff would happen and it would be like 1:00.
The scripts aren’t due till three. “Trevor, it just happened. We got to put it in the show tonight.” And Trevor is like, “Well, wait a minute. Let’s see.” That’s my accent. “Let’s wait today and see what unfolds.” And you may not be first, but you will have the most interesting, and you will have the most nuanced approach to something that people thought that they had already heard and knew everything about. And so that’s kind of why I’d choose to. It’s YouTube and Reddit are the only place where constituents get to talk at length and really explain why they feel the way they feel.
Debbie Millman:
There are two other places that do it, just if you’re ever looking, TripAdvisor. TripAdvisor, hotel reviews. I live and die by them because I travel a lot. And so I need to know where I’m going to lay my head much to my wife’s chagrin.
Roy Wood Jr.:
Yeah. It’s just-
Debbie Millman:
So we’ll start there.
Roy Wood Jr.:
I like those. You can get your dudes from anywhere, but most of the time when people talk on the local news, it’s a 15-second jab. Twitter is quick jabs, and then it devolves into something crazy. Instagram is not really set up for that type of discourse, but I need to know what everybody is already saying. So I can not say that or have a new perspective on that.
Debbie Millman:
That makes a lot of sense. I read a lot about you over the past couple of weeks, and I learned a number of nicknames that people have given you over the years, but the one that really stuck with me for a lot of reasons was from an article in GQ a few years ago where Paris Sashay said, “You are the Black uncle of comedy.”
Roy Wood Jr.:
I’ll take that.
Debbie Millman:
What do you think about that nickname? And is that something you think of as a compliment? Because it was framed as a compliment, and I certainly see that as a compliment.
Roy Wood Jr.:
I mean, well, I figured what she meant was like I’m the good uplifting uncle, not the drunk uncle.
Debbie Millman:
Oh no, yeah, you were the good uncle. Not the creepy uncle.
Roy Wood Jr.:
Every family has two uncles.
Debbie Millman:
Yes.
Roy Wood Jr.:
Yeah. The one that go, “You can do it. Come on, drive. I know you’re only 12.” I enjoy talking to the younger comics. So sometimes it turns into… It’s not really deliberate advice as much as it is. “Hey man, what do you think I should do with this thing?” And I enjoy talking to younger comics because they have their finger on where the game is going. I have a child, I have a day job, I’m on the road. There’s people to talk to and deal with and staff stuff.
So I don’t have time to just be at a granular level to see everything that’s happening on the internet. Something as simple as who’s this new artist? It could be by just being around the younger comics at the comedy cell, like say, Paris Sashay and Derek Gaines or Reggie Conquest. These people help keep me hip to what’s going on so that I’ll know what people are talking about and what people actually give a damn about.
Debbie Millman:
That’s what I call my students, my youth concierge.
Roy Wood Jr.:
I’ll give you a great example. I had a joke about a Chuck Norris movie, and I’m pitching it to Paris and some of the other comedians at the table, “Man, y’all know Chuck Norris. He had these movies,” and then one of them just went, “Man, I’m 31.” And I was like, “You know what? You’re absolutely right.” And then Eagle Witt is like, “I’m 26. Oh gee, I don’t know nothing about Chuck. You mean the exercise dude at two in the morning?” So then I instantly go, “Okay, I need to rework that joke. That joke is not going to be as universal.”
Debbie Millman:
Please tell me it was a joke about Delta Force.
Roy Wood Jr.:
Yeah, it gets to that. It starts with Missing In Action though.
Debbie Millman:
Oh, excellent.
Roy Wood Jr.:
Which if you’ve ever seen Extraction with Chris Hemsworth… It doesn’t matter. We’ll talk about it later.
Debbie Millman:
Yeah. I see a lot of 30-year-olds here just looking at us like, “Hmm.”
Roy Wood Jr.:
But I never set out to be a mentor. I don’t think I am, but I just think it’s symbiotic conversation. I’ve tried to be the comedian that a lot of comics weren’t to me growing up in terms of either not sharing information because they think everything is a competition. They think that there’s only one comedy club in America and that we can’t both perform at the same time, in the same timeline, in the same Spidey-verse or whatever. So you deal with a lot of petty and competitive motherfuckers and I just decided I didn’t want to be that. And I think what I found in talking to other comics is that often, it helps to make me better.
Debbie Millman:
Roy Wood Jr., it has been an absolute delight. Thank you so much for joining us-
Roy Wood Jr.:
Thank you for having me.
Debbie Millman:
… for Design Matters Live.
Roy Wood Jr.:
Thank you. Thank you all.