Ep. 45: Roy Wood Jr. | The Guy From Birmingham

I'll never forget the first time I caught Roy Wood Jr. on stage in LA; his electrifying presence had the crowd in stitches. Now, I'm beyond thrilled to bring that same infectious energy directly to your ears as Roy joins me to peel back the curtains on a career that's had us laughing all the way from comedy clubs to The Daily Show. Sit back and absorb the anecdotes of our shared history, from the heartfelt care package he sent during my deployment to his unforgettable stint at the White House Correspondents Dinner. Roy's narrative isn't just a series of punchlines – it's a masterclass in the resilience and connection that defines the comedy landscape.
 
Cleveland's notorious weather, it turns out, may just be the secret ingredient to appreciating a good joke. In a conversation that meanders through preferred climates and memorable locations, Roy and I find common ground in the oddest of places. From LeBron James' effect on the city's morale to musing over who'd play us in a biopic – Keenan Thompson and Idris Elba, if you're listening, we've got some ideas – we tackle it all. Our banter extends beyond stages and screens, touching on the passions that color our lives offstage, and yes, that includes a shared love for video games and baseball cards.
 
Wrapping this episode is a bit bittersweet, like ending a great night out with an old friend. Roy's candid reflection on bombing at the Apollo Theater is a poignant reminder that our missteps often shape our success stories. This chat isn't just about the laughs we've shared; it's a heart-to-heart on the lessons learned in and out of the spotlight. So, as I extend my gratitude to you, the listeners, for joining us on this journey, remember to stay tuned for more stories and insights that continue to ignite the torch of humor and humanity.

Conversation:
Intro, background of how Martin and Roy met, and sending care packages
00:00 – Time Roy Wood Jr. That is a throwback. More importantly, I'm happy you got back from the from the middle East safely. Jeez. I ended up on USO tours, ironically.

Why life is great right now
06:22 Roy Wood Jr. It's a blessing. I'm sitting in Canada, bro, doing jokes in strange places, which in a weird way takes me back to that year one, year two. It feels like Iron Man 3, where he just doesn't have the suit and has to figure out how to do the job all over again from scratch. It's figuring out the city, figuring out the locals and like comedy is a job. Comedy is interesting in that it's a job that you never feel like you know whether or not you're still doing it well, even when you're doing it. So to finally be in a place where, oh, I can still do this, whew, thank God. I thought I sucked again has been a bit of a relief.

How the industry has changed since first coming onto the scene in 1998
07:33 Roy Wood Jr. For me, I think that the idea of there being a singular linear path to whatever we want to define as stardom, no longer exists. And that paradigm shift needs to be acknowledged and accepted as truth instead of being constantly written off as an anomaly. Andrew Schulz and Matt Rife are two of the highest selling global comedians right now. Neither of them have a hit sitcom. Neither of them have a hit movie. It's just grind and meeting the fans where they are and the streets deciding, yeah, you're worth $40. I'm gonna come see you. You're at 60 or whatever they charge. So I think that's the thing that's different now. It used to be, I need to get in TV to get in film to be a star, then I tour, then everyone likes me and then everyone, but now you can just go straight to the fans and if the fans like you now, you can just go and go tour. And you can skip all of the other stuff. I think we're in a world where scripted television and late night and movies and all of that, it is an avenue, but it is not the only path. Entertainment now, to me in a lot of ways, it's like when you're at the grocery store and there's one checkout lane open, and then a cashier opens up another lane and then a bunch of people leave your line to go get in that line. Imagine being in a singular line at the grocery store and now seven different lanes have opened all at once. And there's TikTok, that's a way, with the idea that stardom is what's on the other side of the register, or fan base, or whatever you define as success. Instagram lane is open, traditional touring lane is open. YouTube lane just opened, podcasting lane just opened. So there's a million different ways to reach people and convince them that you are worth their time and money. At the end of the day, that's all any of this shit is about. Getting people's time in exchange for some of their money. Sit and watch my show. Go to the theater and watch my movie. Listen to my podcast come to my live comedy show. So it's about convincing people that you are above and beyond everything else that is out there, you know? And because there are more direct to consumer models to reaching people, it's a lot more competitive. So I think comedy in a way is no longer being able to be gate kept by the industry people who decide who the next stars are. The streets decide who the stars are now. Only reason most of these artists now still need an agency is because the agencies are in bed with Ticketmaster and Ticketmaster controls all the good venues where you can go make money. So,  if not for that, then we really would be a wide open situation.

With all the traveling, years of hard work, and consistency, what Roy learned most
10:55 Roy Wood Jr. Well, I'll tell you what hasn't changed since 98, is that you still have to have good jokes and you still have to have a point of view. So in the midst of all of this flux, at the end of the day, you still have to be able to do something that connects with people. And if you can make them laugh, great. But if you can make them feel, then you're really in a good position. So speaking of, I'm sorry, go ahead, Ron. So that's kind of where I am now.

If Roy Wood Jr. could combine three comics past or present into one super comic, what three would he pick
12:00 Roy Wood Jr. That's a such a better question than Mount Rushmore. God bless you. Give me Sinbad. Sinbad's relatability and universality. That's not a word, but it is now his ability to his comedy can reach three. He's one of the few comics where there could be a granddad, a dad, and the grandson all together at the show. Give me Sinbad reachability, give me Carlin's wit, and give me Eddie Murphy's charisma. And I think those are the, that would be the super comic that I would set loose on a 90 city tour. Base level ticket, $200. I'll tell you a comic I've always enjoyed is Damon Wayans. I think he's one that gets underrated. Damon is interesting in that. He's such a good actor as well that you forget that he was a beast with them jokes, a beast. And so, you know, he's a guy that I still enjoy watching right now. But, you know, Sinbad was the be-all-end-all, George Carlin was the be-all-end-all for me growing up, Rondell Sheridan as well. If you watch a little bit of me, it's probably Rondell Sheridan after three shots of whiskey. Yeah, a little bit of that. But you know, there's a lot of, there's a lot of like, there's just so many people from those early days era, you know, I didn't even get to mention Chris Rock, but you only gave me three and I'm kind of sprinkling, you know, mad scientist ingredients each. And if you get the wit of Carlin, then you don't need the wit of Rock And Rock's charisma is equal to Eddie's. Eddie's probably a little bit more because there's a little more sex appeal and, you know, all of that stuff. But with no disrespect to Chris Rock's likeability, that's not a word.

Memorable set that bombed and the gift it gave afterward
15:32 Roy Wood Jr. The Apollo Theater I bombed at. The pretty tough one. I didn't get booed, but it's a story I've told in the past, another podcast just about how I knew I was about to get booed, so I cut my set early and said good night. And then I went back out there to get judged when Kiki Shepard comes out to audience, give it up for the first comedian, yay. Yeah. All right, now give it up for the second comedian, boo. And I got booed worse then had I just stayed out there the first time and gotten the boo then. So this idea that you can't run from failure, you can't hide from it, that was a huge lesson that I learned that night in that you have to just be present in the moment. It did not work tonight. But the thing that I've learned most from failure in comedy is that most people have a short memory. Most audiences are not going to remember not liking you. You know, we can't even remember, like it's just, each week is a new opportunity to get it right. And so once I looked at it like that, I became less attached to failure and the sense or the feeling of permanence that is sometimes perceived within it. I don't have that anymore. And so, you know, that was, but it was the Apollo that kind of taught me that lesson of you can't hide from that. Failure's going to find you. When it does, absorb it, and then get back to the grind.

Advice to anyone, whether first time bombing on stage or whatever their pursuit is at the time to best recover
17:34 Roy Wood Jr. Find the people you like and find video of them sucking and then it would give you perspective. Failure hurts, but failure is where the lessons are learned. I tell my son, there's no such things as losses, there's only lessons. Failure is the best educator you could ever get. So, you should embrace failing and look at it as an opportunity to improve. Sometimes within those, like I read YouTube comments about me, I read Reddit comments, because every now and then somewhere in the midst of all of that just random, just internet trolling hatred is a legitimate fair critique about something that I could have done better or that I should have considered. Yeah. And I think within that is growth, especially when you're talking about the daily show and what we do and with regards to trying to present content that speaks to XYZ issue of the day as well.

Unusual habit or absurd thing that Roy loves
19:06 Roy Wood Jr. I always tell other comics, you are who you are on the road…that is the truest version of yourself and your psyche and your nuances because you are alone. And it is the one time where you can really be yourself because you feel like in a hotel, it doesn't count. I'm into jigsaw puzzles, video games. I went to a card expo while I was in Toronto and realized that I still like baseball cards. I still like collecting cards. Like, I didn't think that was something I was still into, but I am. A new habit is going out and recording video of myself on mass transit for my son to watch. Cause he likes trains and cars. So yeah, so I'll go out and record that. I'm not sure if that's like, you know, weird, like I'm not into paying hookers to call me racial slurs or like I don't have kinks or anything like that. No, I'm actually very serene, man. You know, like there's just so much. So much of my life is involved with meeting and connecting with other people that the road is often the place where I do nothing and it's weird in that I enjoy that and that people find that weird. But, you know, I'm comfortable in that place. To me, my idea of a perfect vacation is traveling somewhere beautiful and never leaving the hotel room. And I can't explain it, but that's perfect for me. I just want to look out the window and see it, but I don't want to go out there. I'd rather stay in the house.

If there was a GIANT BILLBOARD that he could place anywhere in the world with his message on it for the world to see, where would the billboard be and what would the message say?
21:35 Roy Wood Jr. Let's go backwards first. Don't be afraid to take chances, no fear. Okay. As quoted in my high school yearbook, still a quote I live by. It would be somewhere cold, that's for sure because I like the winter, or it would be raining, it'd be like 45 and a drizzle. Maybe London? I kind of want to say Cleveland, because that's where I enjoy doing comedy the most. Yeah, Dayton's okay, but Cleveland's more miserable. They appreciate the jokes more. You gotta do the jokes in a place where people are just frustrated. London or Cleveland, you can't get any more different than those two towns. LeBron is the worst thing that happened to Cleveland because he made them think they could always be this good. And then he left. Twice. We're taking down your picture.

If a movie were made about Roy’s life, who would play him?
24:14 Roy Wood Jr. Who would play me in a movie about me? I don't know. It depends on what part of my life you're touching on. That's a good question. There's not a lot of young chubby actors. It would have to be Kenan Thompson. They'd have to just do that digital young-um-up AI stuff. The title of the movie would just be The Boy from Birmingham. Who's your pick to play me? Don't say Denzel.

More info about the guest:
Website - https://www.roywoodjr.com/
IG - https://www.instagram.com/roywoodjr
Facebook: https://www.facebook.com/roywoodjr/

People mentioned:
Jacqueline Miller
Andrew Schulz
Matt Rife
Sinbad
George Carlin
Eddie Murphy
Damon Wayans
Rondell Sheridan
Chris Rock
Kiki Shepard
Kenan Thompson
Idris Elba
Jordan Klepper

Quotes by Roy Wood Jr. : 

• “Failure hurts, but failure is where the lessons are learned.” 
•  “There’s no such things as failures, only lessons. Failure is one of the best educators.”
• “You are who you are on the road, that is the truest version of yourself and psyche.” 
• “Don't be afraid to take chances, no fear.” 

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