Loading summary
Interviewer
You're listening to DraftKings Network.
Larry Wilmore
Deck your home with blinds.com.
Diy or let us install.
Free design consultation.
Plus free samples and free shipping.
Interviewer
Head to blinds.com now for up to 45% off with minimum purchase plus a free professional measure.
Rules and restrictions may apply.
You know by now that South Beach Sessions has to come out west to get the funniest people, to get the best people. Larry Wilmore has been not just a face and voice for comedy in front of your face, but he's been doing a lot behind the scenes as well. His podcast, very popular, an interview podcast, Black on Air with the Ringer. When I describe you as actor, writer, comedian, producer and creator, if I give you the choice of those five, which one of those do you most like? Which is the one that you say that's the one.
Larry Wilmore
You know what I think of all of them is probably producer, I think, because I like putting the puzzle together is my favorite thing. You know, I enjoy being on camera and acting and performing, but there's something about putting the puzzle together that appeals to me a lot, you know, figuring the thing out and which is tied to creating too. You know, creating TV shows and that kind of stuff, which I'm always interested in in the middle of doing at some stage and probably doing several at the same time. So that kind of 3D chess is just fun. You're putting people together, putting ideas together. You don't know if something's going to work, you know, really, till it gets on its feet and then it's a living organism. It's not just, it's not just an idea, you know, so there's a lot that goes into most people, though, who.
Interviewer
Are on camera, front facing. I was expecting. Almost everyone I talked to who has been a standup comedian chooses stand up comedy as the one. But you've made so many things in so many places. For those who don't know, in the creating of the Bernie Mac show and Jamie Foxx, you've done a number of things behind the scenes to elevate the talent of others. And it seems like you get a lot of gratification from that one.
Larry Wilmore
Yeah, you know what's funny about that? I think as a person, I just always felt more comfortable talking about somebody else's thing than my own. So even as a comic, I enjoyed standup comedy, but it is a bit torturous. It can be, but, you know, you get that direct connection with an audience. So there's nothing like stand up comedy in terms of the, the directness that it gives you in the response, you know, I also perform magic too, and say to him, I perform at the Magic Castle. And that's. It's a cousin to stand up. But it's different because you're getting a reaction of wonder from the audience and this different thing that you don't get from any other thing. So that's actually.
Interviewer
I didn't even give you magician. If I'd given you. If I'd given you magician, you might have taken magician over prod. You've been a magician since a very young age.
Larry Wilmore
Correct, kid? Seven years old. Yeah.
Interviewer
So did you. Is that what you thought when. If I'd asked 7 year old Larry Wilmore, hey, what are you going to be when you grow up? It would have been magician. And you did do that. You have done that.
Larry Wilmore
I probably wouldn't have said I'd be that at 7. I would have said astronaut. That's what I would have said, you know, because.
Interviewer
So you failed.
Larry Wilmore
I failed horribly. I never made it into space. Well, and plus, I wasn't sure if brothers were allowed to go into space at that time.
Interviewer
Well, they weren't back then.
Larry Wilmore
No, they were not. I had a podcast with.
What was his name? God, it escapes me now, but he was the first black astronaut who was in the Gemini program, actually.
And it was fascinating to hear his story, talk about it and how he didn't quite make it to the end, you know, because, you know, there was a huge wall against that. But I mean, he basically, you know, he was in all that dream of that and everything in that time. It was so interesting. It was one of the funnest conversations I ever had was talking to him.
Interviewer
And yet his name is forgotten to not just history, but also you who talked to him.
Robert Lawrence.
Larry Wilmore
Because I don't want to get it wrong.
Interviewer
Robert Lawrence.
Larry Wilmore
No, no, no, no, no, no. It's, it, it's, it's the same as another astronaut. But see, I'm just getting.
Interviewer
We don't have to get stuck there.
Larry Wilmore
I know, Dan, it's terrible. I get so forgetful. I used to joke about like if, you know the old saying, if you, if you didn't. If he didn't screw his head on what is the joke like, he would forget it. You have to see, I can't even remember.
Interviewer
He would leave his head at home.
Larry Wilmore
Leave his head at home. Okay, so me, I remember to bring my head. I would just forget to actually screw it. So during the day, I'd be driving, you know, the head would just come Off I go.
Interviewer
Fuck.
Larry Wilmore
I didn't screw my head guy.
Interviewer
Bluford is his name.
Larry Wilmore
No, now you're just making stuff up. No, it's Dwight. And it's. But it was the same as the other. As the white astronaut who did the first spacewalk. See, that much I know.
Interviewer
Okay, so we've really gotten stuck here in some space quicksand.
Larry Wilmore
But this is.
Interviewer
No, but this is where the magic took us. Because I want to talk more about the magic. You. You are a magician who has performed in front of crowds and. And you are saying that the best feeling is the awe and wonder. It's better than laughter.
Larry Wilmore
There's nothing close. No, especially today. I feel like today adults rarely get to experience wonder. You know, they experienced as children. And the last time as adults, I think we collectively experience wonder, arguably, I would say, was the moon landing. You know, where the entire world didn't matter what your age was. Truly experience what wonder feels like. You know, there's nothing had existed like that. You know, maybe some events, but not collectively like that. But especially with technology and advancements and stuff, people are so like. I mean, AI, the most incredible thing in the palm of your hand. People like, eh, whatever. What the. This is incredible, these advancements. But people are just, eh, whatever. So magic takes that away. It takes people back to the feeling they used to have when they were children. When that's stripped away from you. You don't get to have that feeling after a certain age.
Interviewer
And so how do you. How often do you do this? Because you mentioned performing at the Magic Castle.
Larry Wilmore
Right. Well, I practice it every day, you know, which I've done most of my life. But I don't perform it all the time just because I'm busy doing other things. So I choose times when I can go out into the world. But last year I did a special little mini tour because I was really interested in the election. So I decided to put together kind of a politically themed magic kind of experience night, which was kind of fun.
Interviewer
Do you have cards on you now?
Larry Wilmore
I usually do. And I was gonna say no, I probably shouldn't bring them. So I actually had that conversation with myself.
Interviewer
So we. And we. You failed again. You failing. You've been waiting all your life for somebody, somebody to just ask you, do you have the cards on you right now?
Larry Wilmore
Is there deck of cards here? Because if someone has a deck of.
Interviewer
We'll send someone out.
Larry Wilmore
I could do something in front of. No, it's not preset up.
Interviewer
We'll have it at the end of the show, we'll get somebody to go get something. But, but when you, when you talk about. You were, as a child, you were a science and magic nerd, right? And you were. How do you get to comedy from there?
Larry Wilmore
Well, comedy, I always loved it too. At the same time, my first love was Flip Wilson on television. You know, here's a black performer, you know, who's the funniest thing I'd ever seen, you know, And I used to imitate him and my dad used to have us do skits in our living room and stuff like that, you know.
Interviewer
Is he legitimately at the time the only black comic on television? Like, he was the only one to.
Larry Wilmore
Have his own show and his own variety show. Nat King Cole had a variety show, you know, he was a comedian, of course, in the 50s, and it was canceled because the south just didn't want to buy products, you know, that were advertising on a black person show or whatever, even though he had the highest rated show. So it was kind of a. It was a revolutionary act to have your. A variety show, you know, as a black performer. At that time, it just wasn't done. I didn't know that much as a kid. I just noticed that there's nothing like it on tv, you know, And Flip Wilson was so funny, you know, it's funny that he's not talked about as much now, but he was huge at the time, you know, just so infectiously funny. So I kind of, when I looked at that as a kid, not knowing I would be comedian, but I used to imitate him all the time, you know, I would read everything I could about him and that kind of stuff, you know, some. He was kind of my first comic hero.
Interviewer
I think it's interesting though that more your. Your comedy runs more Jewish than it does black, right? In terms of the. The roots of your comedy, it really does.
Larry Wilmore
You know, Marx Brothers were a big influence early on. Even people like Jack Benny, you know, here's some older names. Sid Caesar, I remember seeing that kind of stuff. Mel Brooks, when I got a little older.
I have many some friends, Jewish friends, and the kind of rhythm of that. Neil Simon, I'm a huge fan of his plays and that kind of stuff. But there's something about the use of language and the rhythm and the point of view and all that kind of stuff I really always kind of related to in Jewish humor.
Interviewer
What were the schools you were going to like growing up?
Larry Wilmore
Just. You mean, like just primary schools?
Interviewer
I'm saying, are you in black schools? Are you in like, what what company are you keeping?
Larry Wilmore
Growing up, I was always in mixed environments where, as a black person, always in the minority. So when I was real young, we went to the local public school. By fifth grade, we went to Catholic school.
Public school was. Yeah, it was kind of.
It was a little bit diverse, but not that much. The neighborhood was.
It was still a mix of black and white and Mexican and that kind of stuff. I grew up in Pomona, California, but once I went to Catholic school, there were hardly any blacks there, and it was mostly Mexican American and white. And then my high school was mostly white, few Mexicans and very few black people. My friend Rick and I, we were the only blacks in our class for most of the four years there. You know, I think there was maybe one other person, but that was it.
Interviewer
And how was that? Did you fit in?
Larry Wilmore
It just is what it is. You know, at the time, I didn't. I mean, I would make jokes about it or whatever, but, you know, I. I still lived in a neighborhood where there were a lot of blacks. I still had a lot of friends, so that was around, you know. But I always felt like, even as a young person, and I say I always felt like I was at family reunion, but I wasn't in the family in the situations. So I always felt on the outside looking in, in many different situations. School was just one of them.
Interviewer
What are the others.
Larry Wilmore
Socially?
Because I was in different things, I felt like I never fully belonged in one of them, you know. So sports was a big deal in my neighborhood. I grew up in a real sports neighborhood. We had different people that went, played pro ball, that came out of my neighborhood, even just on my block alone. On my block alone, few doors down. Bill Duffy, who's a big sports agent now, right, he was like my older brother, you know, he went to Catholic school, too, went to Damien High School, in fact, where I went to a couple of houses from Bill was Greg Ballard, played for the Washington Bullets. He went to Gary High. Around the corner across the street from him was Cornell Webster, played for the Seahawks, eventually went to the local school that was just the half block. So that was the environment I grew up in. Sports was huge to me as a kid, you know, and actually I wanted to play sports more so than I wanted to be a comedian or that type of thing at a young age. I should say that my dad played college football for a little bit, a little semi pro back in those days.
Interviewer
So you failed.
Larry Wilmore
They had that type of thing. This is an interview about all my fails.
I'm so Happy I was in that world, though, you know, I still think sports is the best way to learn everything you need to learn about life, you know?
Interviewer
Well, it sounds, though, that that laughter was the connective tissue, though, right? In all of these places, you're going to fit more if. If you're providing laughter, I suppose.
Larry Wilmore
Yeah, but I was just interested in many different things, and so they each gave me something different, you know, But I. I never thought of laughter as a tool or something back then. It was just, you know, it was just things were funny. So you just.
Interviewer
So where does that come from, though? Have you explored that at all? Like, what was happening in your. In your family? That was rewarding that. Right? Because I know these are formative years you're talking about. If, you know, a teenager just wants to sort of fit you, feeling like you don't fit much of anywhere. Right. And so you. Now you've got to choose, what am I good at? I've got to make decisions about what my future looks like or what do I like. And at some point here you're gravitating toward the arts. How does that happen?
Larry Wilmore
Yeah, that was a conscious decision. Once I got into college in high school, I wasn't sure about anything. My life kind of.
It felt like it was falling apart a bit in high school, the life around me. My parents were divorced at that point. Our home life was kind of falling apart. My mom was having a tough time. Looking back, she was going through kind of a nervous breakdown. My sisters were having a tough time, you know, hanging out with some bad elements, doing drugs, things like that, you know, And I was going through a tough time. Looking back emotionally, I had always been an excellent student, and it kind of let my grades go by the time I was a junior, probably sophomore, junior year, and I was conscious of it, too, kind of ashamed of it. But I remember I kind of started hiding out in my activities, more so than anything else. And.
You know, it's funny that.
I knew that I could accomplish things, but I also felt like I was failing, because you bring up failing right now, which is funny. There was a part of me that wasn't accomplishing the academic career that I felt I should have had. And I was too. At the time, I. I was just too emotionally buried, just buried emotionally, you know, there's just too much going on for me to take. I didn't have those words for it back then, but definitely that's what was going on. And I. Academics just didn't. Just didn't continue to be the thing, you know, and I, I got a scholarship to high school. I was always a star student in that, but I just couldn't keep it up. But I escaped into sports, into theater. Magic was always there, you know, and kind of into the things that kind of brought me more satisfaction on that level. Then in college, I had to really start thinking about my life, you know, what am I going to do? And that's when I put cold water in any sports ideas too. I was very lucky that I grew up in such a competitive sports environment. I knew what it took to be like an athlete at a certain level. And I knew I wasn't that either physically or you just, you know, you didn't have the tools. I was pretty good though and played in different sports and was even MVP in some things. But it's just different at an elite level, you know. Very lucky that I had was able to see that. So I didn't have delusions about that, you know, so I didn't waste my time in that. So I decided probably my first or second year in college that I wanted to pursue the arts, you know, first as an actor, you know, and a standup comedian, a thespian first.
Interviewer
Right, Like a serious actor first.
Larry Wilmore
Absolutely, yeah.
Commercial Announcer 1
Get ready for Jake versus Joshua Judgment day. A colossal global showdown shaking the world of boxing.
Larry Wilmore
Jake El Gallo De Dorado Paul, the sport's biggest disruptor, steps into the ring.
Commercial Announcer 1
Against Britain's own Anthony AJ Joshua, the two time unified heavyweight world champion and Olympic gold medalist. This eight round heavyweight mega fight pits Paul, swagger and superstardom against Joshua's power, precision and legacy. It's youth versus experience, fame versus force.
Larry Wilmore
The biggest test of Jake Paul's career.
Commercial Announcer 1
In a battle that could redefine modern boxing.
Larry Wilmore
Watch Jake Paul versus Anthony Joshua tonight.
Commercial Announcer 1
At 8pm Eastern, 5pm Pacific live on Netflix.
Commercial Announcer 2
You ever find yourself late night scrolling, adding stuff to your cart you absolutely don't need? And then you see the beautiful glowing purple shop pay button.
Larry Wilmore
Boom.
Commercial Announcer 2
Checkout done. You didn't even have to get up and find your wallet. That, my friends, is Shopify magic. That little purple button means that store is powered by Shopify. Which doesn't just make it easy to buy, but ridiculously easy to start and run your own business too. Whether you're a giant like Mattel or Gymshark or just launching something weird from your garage like Greg Cody's garage, Shopify has your back.
Larry Wilmore
Let's be real.
Commercial Announcer 2
If we can run a show with this much chaos, you can run a business with Shopify with Hundreds of beautiful templates, tools for payments, inventory analytics, marketing. It's all in one place. And yes, that purple button. It's why Shopify has the best converting checkout on the planet. Shopify. It's how real businesses get built. If you want to see less carts being abandoned, it's time for you to head over to Shopify. Sign up for your $1 per month trial and start selling today at shopify.com batard go to shopify.com batard shopify.com batard.
Interviewer
Let'S go back though, for a second here. So when you say you're buried in your feelings, is the divorce the primary thing that's causing that or.
Larry Wilmore
Not necessarily the divorce. It's more the lifesty. You know.
It'S just everything was just chaotic. It seemed like there was no order to it, you know, and my brother and I, I know growing up, my brother Mark, who I lost a few years ago, we used to make each other laugh. That was part of our tool of doing it. And I've talked about this before. One of the games we played when we were younger, when my parents were still together, in fact, we would play make me laugh to go to sleep and that kind of stuff, you know. And so my brother and I always used comedy together. It kind of united us in terms of, you know, just dealing with things. But there was a certain moment where I had to bet on something, you know, and, you know, I just went with the passion of it. I actually wrote an article on LinkedIn a few years ago about my decision in college when I decided to do that, I was selling books door to door and I went into so many people's homes then where.
So many people's homes where they just kind of, you. You saw where it just didn't work out for them. Right. And I met so many people where I saw in their eyes that, yeah, the life just didn't work out. And it really affected me on like a cellular level. It was a real turning point. And I thought, you know what? I'm going to devote my life to doing the thing that's going to bring me some happiness and some joy. You know, I'm not gonna do this or that, whatever. And that's when I decided to devote myself to really being out there.
Interviewer
What an amazing wisdom to accrue selling of all things.
Larry Wilmore
Book. Yeah.
Interviewer
Books door to door. Which seems like a truly terrible job, but what you're doing is walking into unhappy living rooms where hope went to die.
Larry Wilmore
Absolutely. And we started the summer. What it is, is College students, we gathered in a place in Tennessee, Knoxville, Tennessee. And they do this whole week where they give you these inspirational sayings and all this stuff. And there was something about being isolated that. And it was. I was in the down arrow of my life then, too, of feeling a bit despair of not knowing if things are going to work out or whatever. And it really bolstered me, you know, it really inspired me on a lot of different levels, you know, but also.
Interviewer
Made you choose what you don't want. Right. You learned what you wanted from making sure that's not what I want. I don't want my living room to be someplace where I didn't chase the things that I wanted and my life didn't work out.
Larry Wilmore
And I set up some working principles for my life at that point, too. One of them was success is in something that I went after when I decided to do what I really wanted to do. That is the definition of success. So I started my career as a success. And the career was just the journey and the example of it. Huge, huge thing. Because emotionally, I wasn't tied to a destination, I was tied to a journey. So all the ups and downs are examples of my particular success. The success was the decision, you know.
Interviewer
That's an amazing thing to know that.
Larry Wilmore
Absolutely. So lucky that I was able now. I read a lot of inspirational books during that time, you know, and really did a lot of research. I call it research now. But at the time, just trying to find this or whatever and, you know, just from absorbing, I think a lot of that and what success has meant to different people or that type of thing, you know, part of it may have been a lifeboat for myself, too, emotionally, who knows?
Interviewer
Well, I imagine magic was something like that. Magic is almost a literal escape from. I'm gonna get away from my number.
Larry Wilmore
Yeah. And it's funny because magic, it was never a way for me to do something. It was just always a constant companion, you know. But I never viewed it as something I would do for a living or that type of thing, you know, it was just something that I always. That I knew that I just loved. And it was just there all the time. So it wasn't. But it's funny that comedy was, you know, that seemed like a way to do something, but acting at the same time, too. I was looking at both of those things and trying to figure out how to do it.
Interviewer
I want to talk about some of that and the career stuff, but before we get there, like, when you say chaos, chaos of living, how long are we talking about there. What's the age period that you're talking about when you're remembering chaos and what are the relevant details that sort of shaped you on what you wanted and what you didn't want from life? You just gave me a pretty amazing one. Usually things aren't quite that clear.
Larry Wilmore
Yeah.
I would say from early 70s, I mean, arguably some of it happened before then, but definitely early 70s until let's say my high school graduation. 79. Let's take those years, nine year period. My parents are split at that point. You know, we really didn't have a lot of money. And.
I remember the not having money was a big thing too. And I remember one Christmas, my brother and I remember this vividly. Or we had a tuna helper for Christmas dinner like that. That's what we had, basically. We always made fun of it because that's the tools we had. But like, man, this is ridiculous, you know.
And I now I know that there's like hoarder genes in my family, you know, on both sides. But our house was always a mess, you know, no rhyme or reason for that. You know, my mom would spend a lot of time just working and stuff like that, but she was going through her own thing and was emotionally just, you know, going through a tough time. And as a kid, it's just tough to see that all the time, you know.
And like I said, my sisters were really having a tough emotion time. It hit them the hardest emotionally. So that's why they were choosing bad friends and these things. And here I am, you know, model student kind of kid trying to go through life and all this stuff is happening around me. I was. I was ashamed to have people from my house because it was a mess and it was just. Everything just felt broken. So it was tough just dealing with all of that during that time. And. And a clarifying moment for me and my brother was we were in the house once and there was actually a hole in the roof. Like the saying the roof had actually caved in was literal. And we both looking at that just. You got to be fucking kidding me. We're just looking at that thing, thinking that. And I said, you know, this is what I said to myself, I am not going to live like this. This is not going to be my life. A life of this quiet desperation of having your world just implode and feeling.
Interviewer
Powerless against it, you know, and college becomes an escape. It becomes.
Larry Wilmore
Yeah, first, I didn't have direction at first, you know, I went to junior college for a couple years and trying to Find things out. Ironically, at that time, my dad had decided he was a probation officer during that period. And he decided he wanted to go back to school and become a doctor. And we were going. He had to take some pre med courses first. And he was going to the same junior college as me, you know, and he was making the dean's list all the time. And we had the same name, you know, and I'd be walking around. Yeah. And made that dean's list again. I was, you know, of course, I had already thrown away my academic career at that time, so I was just escaping in the theater department during those years and that kind of stuff. Working at a gas station part time, you know, still not knowing it.
Interviewer
You had a lot of bad jobs.
Larry Wilmore
Those are good jobs, Character building jobs, you know, character building jobs, but unpleasant.
Interviewer
Jobs, I guess, is what I should have said instead of bad jobs. Yeah.
Larry Wilmore
Not what you would choose for a living, but I advise young people to do jobs like that because they're just, you know, those are good character building jobs, I think, you know, and you.
Interviewer
Get to college and now you're. You. You feel something in theater class.
Larry Wilmore
Well, I was in theater. Cause, you know, that's what I basically had chosen to do, but still not knowing what's going on. But it wasn't until that summer where I had that clarifying moment that, yes, this is what I'm gonna do in my life. And it wasn't. And soon after that, that next year, I got my first kind of TV gig. I got a recurring role in the Facts of Life. I played a couple episodes and. And I got a part at the Mark Taper Forum in their improvisational theater project. Was able to join Actors Equity. So things started happening once I started setting that up for, yeah, this is what I want to do. And after that summer, I dedicated myself to really doing standup comedy. I had a couple of starts and stops in Stand up, where I tried it and then stopped and then tried it again. I got intimidated the first couple of times, but at that point I decided, all right, I'm going to sit down and just write jokes and just really try to do this.
Interviewer
Well, I want to talk to you about your first two shows because. Or your first two efforts at doing this. But before I do this clarifying moment, what is the clarifying moment moment? Like when you're saying there is a moment of divinity where you're like, nope, I'm pretty clear on this is the path I'm going to choose. Or did you. Was it. Was it the the door to door sales.
Larry Wilmore
The door to door thing. Yeah. That's when I had the clarifying moment that I have to choose this, you know, do you remember the visuals on this?
Interviewer
The sights, the smells, all of it?
Larry Wilmore
I remember all of it, absolutely. There were a couple of things that were interesting that happened. There was one time when we were still in Knoxville and they were giving us all the information and everything, and some of it was Christian based too, and that type of thing. And at one point in my life, I thought about becoming a priest or brother or that type of thing. I was very much into the Catholic church and I was an altar boy, served in that type of thing. I was very faithful in the church. And I remember kind of having a vision at the time. I was just sitting there and I saw myself holding a book and there was light coming out of the book and I was in front of a family, you know, and it just moved me to tears, you know. I don't know why. The feeling was just overwhelming, you know. I don't know what it meant. It was. It was so powerful. That image I still remember today. I still remember that night waking up and just crying, you know. And I, to me, what I took it as. I have to start doing this, you know, like, this is. This is where I'm supposed to be. I'm supposed to be in front of people doing something. Whether it's. I've, I think internally, I've kind of internalized it, I think over my whole life as a life of service for people, you know. So even in showbiz and the advice I give to young people, even today is I always say, look at. If you're going to go on show business, which is really tough, look at it as something you could put something into rather than something you can get something out of, you know, like, what can you add to it? How can you leave it better than it was than you were before, as opposed to what can it give me? How can I be served in it? That is a losing proposition.
Interviewer
Well, you say. You say it's a losing proposition, but I believe it's. The lights for most people are what can I get from it? Not what can I give to it.
Larry Wilmore
That's exactly right. But you can never be done with what can I give? You know, but you can be done very quickly with what can I get, you know?
Interviewer
Well, that. That's a life principle you just espoused right there. Like, if you live your life in service of others, it's right. It's going to be Less empty than if you're living in service of yourself.
Larry Wilmore
It frees you up. It frees you up in a way where you're not in an improper relationship, let's say, with it, you're in a proper relationship with it. Because many people in an improper relationship with it, they define themselves as that, you know, like in golf, you know, golf is something that I love because it's such an obsessive thing, you know, I'm talking about. But it's funny how golfers equate themselves with their score, you know, like they're in 82 that day, but they take it personally that they're, that it's like you're not your score. But that's how they take it emotionally, that that's who they are.
Interviewer
Well, I mean, show business is a poison there.
Larry Wilmore
Showbiz is that so you're the failed audition. That's who you are. That's how you feel that day. And it's wrong, you know. But many people in showbiz take the results of showbiz or the trappings of it as who they are, as their identity. And you gotta separate those things, you know, that's an improper relationship, is what I say you have to get into a proper relationship with. It's an endeavor, it's work, it's this, it's that, whatever it is. But it's not who you are, it's what you do, you know, and understanding those differences, you know. Otherwise, good luck.
Interviewer
Yeah. Well, where did you figure out, where along the path do you figure out? I like helping people more than necessarily.
Larry Wilmore
It wasn't a conscious thing, but that kind of came through, I think. Just, you know, I, I, I'll ascribe it to the Catholic values that I had, that it's more life of, of service, you know, that type of thing. I've always said the difference between Catholic and Protestant in my mind is like when, and sorry, Protestants and bringing this up. But because I've been to these churches too. I went through a period of doing that stuff. I where I always felt like people, if you're Protestant, you go to the church to get something from God, you know, like. And people talk about this very famous. Sometimes God's their butler. Oh, yeah. I pray to God I got my car, you know, I got this and everything, you know, or God's their valet or whatever. What are the blessings God's going to give me and all these things. But it's always God is doing something. He's your personal valet or he's, he's he's your wish list, you know, he's your wedding plan. Whatever he is, he's providing something for you. Whereas Catholicism is kind of the opposite, is what are you doing for God? You know, you have to do these things. You have to perform these services. You know, you even have prayers you have to do that are certain, in a certain order. You have sacraments that are this. And so it's more of a. No, no, sorry, sorry. MF you have to. You have to do the one. The thing for him, not the other way around. So was that relationship, you know, of a. Of a life of service that I've always kind of held in my bones, I think, from early on.
Interviewer
Is there anything on the resume that is most gratifying to you there?
Larry Wilmore
Like, from that? It's not in the resume, but I've dedicated a lot of my career to helping younger writers come up and performers and that type of thing. Still doing it now, but I don't publicize a lot of that stuff. You know, it's more quiet, but that's what gives me a lot of joy and satisfaction and that type of thing.
Interviewer
You. I've. I've read you say that I'm. I'm the king of overseeing projects that have not yet been seen by anybody.
Larry Wilmore
Well, yeah, some of them don't, and some of it is just, you know, just being there for somebody to help them, you know, do whatever, you know. But whenever I've served on boards, I've been on the Writers Guild board and that type of thing, I saw it as, okay, I've had some success. I need to make sure I'm giving back. So I've always kind of had that in my mind, whether it's a, I don't know, you're kind of doomed by that or whatever. But I've always approached it that way as opposed to having any ambition to be on a board or to be a president of the Guild. Like, I don't have that kind of ambition. It's always more tied to service.
Interviewer
Where have you had along the path the most fun in the doing? When I put in Living Color in front of you or the Bernie Mac show or Jamie Foxx or any other.
Larry Wilmore
I've been really fortunate, you know, my career. I've had so many fun shows that I've worked on. The writers room is the funnest. When you asked me earlier, the thing that I probably get the most satisfaction, it is producing. But the funnest place to be on any show is in a comedy writer's room. And Living Color was a ridiculously fun writer's room to be in. There's. I have not been on another one that's been quite like that. And for all the factors.
Interviewer
How early was that in your life? So you're.
Larry Wilmore
That was my first gig.
Interviewer
Oh, my God. You gotta be shitting me. That spoils it for everything.
Larry Wilmore
Absolutely. I start at the top, you know, with the hottest show on television. We're getting Emmy nominations, All that stuff. It's culture changing, all of that stuff. Teaching me all those lessons. It's black LED content, you know, which was unheard of in those days. You know, if there were black shows on television, they were usually produced by white people, you know, not black. Producing their own thing, you know, this is when Spike started doing his movies. That influenced me a lot too. So much about that influenced me. But the writers room was so much fun. There was things that we said in that room that we'd all go to prison right now because we'd all be cancelled because you just can't say all that stuff, you know, which is hilarious when you think about it. In fact, we used to come up with decoys that were so outrageous that we'd get the thing that we want in the script to get through, which is hilarious. You can't say that and say, all right, well, at least give us this throw you. Oh, absolutely.
Interviewer
You'd actually throw them things that you knew were going to not get past a thousand percent.
Larry Wilmore
Yeah, absolutely.
Interviewer
See, those are those that had to be so much fun to be with those rebels creating that thing and getting the instantaneous feedback that you would in. In Stand up comedy.
Larry Wilmore
Yeah, and Stand up taught me how to. How to make people laugh. It really taught me that, you know, and writing jokes and that. And Living Color really taught me how to manufacture that in, you know, large quantities all the time, and how to produce that for an audience, you know, two different places. Huge lessons. You know, I learned so many lessons on how to do television from being in Living Color because we all feared for our jobs all the time, you know, and we had to produce so much material all the time, you know. But it was a real fun group of people too, who just wickedly funny. And, you know, it was. It was great. So that was probably the all time. But I've been lucky. I've been, you know, the PJs. We had a great writing staff, you know, got to work with Eddie Murphy on that, you know, which was amazing. You know, really funny stuff. All the stuff I did at the Daily show, you know, for years, being able to collaborate with Jon Stewart one on one, that type of stuff. Nothing ever like that. The Office, you know, no one really knew Steve Carell a little bit from. From the Daily show, but not really. And being, you know, being able to figure that show out from the beginning with everybody was huge. I mean, I've been so lucky of the different things I've been on, you.
Interviewer
Know, I remember seeing on, and I think I've told this story before, but comedians in cars, getting coffee, Garry Shandling and Seinfeld talking, and both of them just sort of having the unique experience of understanding how hard it is to make something look that easy.
Larry Wilmore
Yeah.
Interviewer
How hard it is suffering involved in it. Is there anything in here that you would say was so pressurized that people might have on the outside thought it was fun? And you're like, it's not as fun as you thought it was?
Larry Wilmore
Well, I'm talking positively about unliving color. But my joke during that time and even for years after, where I said, people said, well, how was it working in there? I said, it was the worst of times. It was the worst of times.
It truly was the worst of times, to quote Dickens, you know, and it was. It was terrible in terms of. I mean, it took everything out of you. You thought you were gonna get fired every day. There was a lot of backbiting. I mean, every emotions that could be on there, every type of character that could exist on that, you know, was there. It was the hardest job ever. And writing in general, like, I don't enjoy writing, but I'm compelled to do.
Interviewer
It, you know, same like that. I feel it's fulfilling, but only after having done it. I have not yet gotten to the free flowing. I'm doing that. Oh, come on. Don't tell me that I'm never going to get to free flowing. I'm doing so much work to trying to get to free flowing. That's it. You're telling me I'm doomed?
Larry Wilmore
I'm telling you you're a masochist. That's what I'm telling you. Like you're in an improper relationship right now. But the problem then is that you're good at this. That's the thing, you know, and being good at something doesn't mean that you have to like it, you know, it just means that you're good at it. And that's. That's another distinction, you know, by the way.
Interviewer
But wait a minute. You like having written.
Larry Wilmore
I like. I love having written. As Dorothy Parker says, You know, hate writing, love having written. But the process of writing is torture. People say, larry, why do you write? I say, because I have a deadline. Otherwise why, why would I do that? Why would I put myself.
Interviewer
But you just said compelled, though. You just said compelled. That doesn't have much of anything to.
Larry Wilmore
Make a living with. You know, I want to be in showbiz, you know, that writing was something I could do. To do that I have. When I think about my creativity, it's rooted in expression, not acceptance. You know, many performers, especially actors, I shouldn't say that. I should say there are many performers or the writers, actors, whatever, the fulfillment that they give is a reaction, you know, stand up, comics especially, it's the laugh that makes it. For me, it's different. It's the crafting of the joke, you know, and them appreciating what I just did is, is what gives me the thing. So it's more the expression that drives me.
Interviewer
You've got a real unique relationship with this. When you say that, I already feel like a success for just having tried it. Right. As a career choice, if that's your starting point, you've placed your expectations in, in, in such a low place that you're able to.
Larry Wilmore
What's not expectations?
Interviewer
Well, it doesn't have expectations if you're arriving, if you're saying you're just trying.
Larry Wilmore
No, that's not correct. It's relationship is what we're talking about. What relationship do you have to it? You know, are you a prisoner to outcomes emotionally, or do you have it in its proper perspective and understand that they're going to be highs, there's going to be lows, but if you're in it for the long term, you understand that you're in the proper relationship with it. You know that it's not going to be, you know, this thing the whole time, you know, just being. I'm talking about relationship now. Expectations are separate. You know, where do you. Where do you see yourself in five years? What do you want to do? And you work towards those things and you would be disappointed if you didn't have that. So of course, of course I had ambition and goals and all that kind of stuff. But it's different from the relationship that I had to the business. For instance, if the business goes away from me, what. How does that affect me? Is that going to crush my life? If I'm in an improper relationship, it will, but if I'm not, then won't. Because I know I have tools and I value and you know, I Have family that loves me.
Interviewer
This is the wisdom accrued over a lifetime, though, right? This. You weren't always.
Larry Wilmore
No, I was in a proper relationship with it from the beginning. No, this is what I'm telling you. This is the moment that I had, you know, because I could not allow that. No, I'm not saying that I. That you always feel good about this or that. But I had to check myself along the way constantly. And this is a constant checking in that I'm in that proper relationship with it, that it's not doing the wrong thing to me, because sometimes it does. I'll give you an example. When I have my own show on Comedy Central, the Nightly Show. This is everybody's dream, right? One of my dreams, too, to have my own show. So the promotion for was so overwhelming because my face was on all these posters everywhere. It was in Times Square, it was here and here. And I was like, man, this is a lot of attention put on an individual. I had, like, a conscious feeling of that. I'm like, I understand why people can get out of control when they get in the bubble like this. Everybody's kissing their ass, you know, you're not in any authentic relationships all of a sudden because people either may want something or they feel afraid to say something. It's a horrible position to be in, you know, and if you.
Interviewer
Having all your dreams come true.
Larry Wilmore
No, but listen to what I'm saying. Not having all your dreams come true is not being in an authentic relationship. That's what I'm talking about. So the dreams come. There's nothing wrong with having that happen. But the fight to stay in an authentic relationship with the world and the people in that world is the fight, you know, and if you don't, you start. Your life becomes inauthentic and you are going down a bad road.
Interviewer
Yeah, but not everyone has the clarity or wisdom to see that. I saw one of the many people that I respect who saw it, but there aren't that many, actually. Ta. Nehisi Coates saw what happened as soon as fame arrived. And he's like, I gotta go running back to just write books, because this ain't healthy here.
Larry Wilmore
And at first it doesn't make sense. Look, Chappelle did that when he. When he left. You know, a lot of the attention wasn't the right type of attention. I understand where that. Where he's coming from, from that. But most people just look at the money part of it or that because they think that's the thing, but not necessarily. For some people, it can be. And some people naturally are in a good relationship. They never have to think about it, you know, they naturally have a good support system around them. They naturally choose family relationships properly and all that stuff. And they don't let that stuff bother them. They don't have to think about. I had to think about it.
Interviewer
Well, you're also saying you're. When I say all your dream come true. Because I would imagine the Nightly show is.
The mountaintop of all of your life's learning and whatever it is you were feeling on seeing your face on Times Square would represent. Okay, I've arrived at the top of the mountain so far of what my ambition has been. I've got that wrong.
Larry Wilmore
No, the thing is, I was very lucky because it happened to me when I was 52. And I said, you know, Larry, will fame change? I'm like, no, fame had its shot, you know, when I was in my 20s, it had its shot to ruin me, you know, but I'm 52. Excuse my language. I said, fame can go fuck itself at this point, you know, I'm way too old to corrupt now. I've had the ups and downs of showbiz. It's coming at the proper time in my life where I have the tools to handle it now. You know, by the way, no matter what my observations are now, if I had had that show at 22, completely different, who knows what could happen? Like, I feel sorry for people. I don't know how Eddie Murphy's done it for so long. His life changed at 19 forever and ever and ever. He's never as an adult really been in a. What we call a normal relationship with the world. Can you imagine that? And just not saying this isn't a negative thing about Eddie, but when I looked at him, I realized that the only. From what I could see, the only real authentic relationship he had, the only people in his life who could probably tell him no authentically were his kids, you know, because everybody else is affected by all that fame.
Interviewer
You know, maybe that's why he's got so many.
Larry Wilmore
That's why he has 11 kids. Exactly. It makes sense to me.
Interviewer
I can keep little mass producing authentic relationships.
Larry Wilmore
But doesn't it make sense? It really does. It is his happiness plays whenever he talks about them or he's in it. He's the happiest. And I get it. I get it. And I doubt. I doubt seriously, at 19, he thought of having 11 kids. I doubt seriously. But the thing I think has been the vacuum is those relationships.
Interviewer
You see, you've seen from every angle. What a Contaminant showback.
Larry Wilmore
Absolutely, 1,000%.
Interviewer
And you probably have a healthy fear and respect for just how poisoned all relationships can get from every single angle. With success.
Larry Wilmore
Yeah, success and bubbles. So I talk about politics a lot too. And to me, a lot of our fractured discourse in politics is because of bubbles, you know, and the bubbles that people get in doesn't matter the side. And people hate this thing. They call it this. Both sidesism. Sorry. That it's true. You know, it doesn't. The thing. The content itself is not the issue. It's the bubble that's the issue. You know, and people don't. When people are in bubbles, they. Most of the time, they don't even realize that it just feels normal to them. But. And anything outside of the bubble seems so foreign to them. And it's. It's many times it's just rejected out of hand, you know. But the most dangerous bubble to you as a person is the no accountability bubble. You know, if you have. If there's no accountability in your life, that's a very dangerous bubble. The tools you need as a person to get through that. I don't have those tools down, by the way. If my life has no accountability all the time, it would be terrible for me. So I'm lucky that, that that show happened for me later because I might not have had. I didn't have Those tools at 22 that I had years later. You know, I was at the beginning of some of that thinking, but it wasn't in my life, you know.
Commercial Announcer 1
All right, guys, the holidays are here. We got Noche Buena down here in Miami. Super important, by the way, which means a lot of my favorite memories start the same way. Oh, I an ice cold Miller Light. I crack open the middle light, look around at the friends and family, think. Yep, we are definitely in the prime time season of the holidays. Whether it's a late night hang after the holiday party or standing around a fire pit with the family, or like a hacina Miller Light. Just fits perfectly. It's the taste you can depend on. Brewed for flavor with simple ingredients and malted barley. Rich balanced toffee nuts. I knew you were gonna show up and I was telling the people about the Kajachina and we can share this. Mic, want to come over here?
Larry Wilmore
When I hear. I just walked by, I heard you talking about Miller Light, I'm like, I need it on this. It's the weekend, and it's time for.
Commercial Announcer 3
The boys to have a Miller Light.
Commercial Announcer 1
Exactly Right. Chris is going to have Miller light in about 20 minutes.
Larry Wilmore
5 o' clock somewhere.
Commercial Announcer 1
5 o' clock somewhere, baby. Miller Light. Great taste. 96 calories. Go to miller light.com beach to find delivery options near you. Or you can pick up some Miller Light pretty much anywhere they sell beer. Tis Miller time. Celebrate responsibly. Miller Brewing Co. Milwaukee, Wisconsin. 96 calories and 3.2 carbs. Carbs per 12 ounces.
Commercial Announcer 3
One touchdown can change everything. The crowd, the momentum, the entire game. It never gets old. Feel that same rush with DraftKings Sportsbook, an official sports betting partner of the NFL and Missouri. Listeners, listen up. DraftKings Sportsbook is now live in the Show Me state. New customers download the DraftKings sportsbook app and use code BEACH. That's code B, E, A, C, H. Bet five bucks and get $200 in bonus bets. If your bet wins. In partnership with DraftKings, the Crown is yours. Gambling problem. Call 1-800-GAMBLER in New York. Call 877-8-HOPENY or text hopeny467-369 in Connecticut. Help is available for problem gambling. Call 888-789-7777 or visit ccpg.org Please play responsibly on behalf of Boot Hill Casino and Res. Pass through of per wager. Tax may apply in Illinois, 21 and over. Age and eligibility varies by jurisdiction. Void in Ontario, restrictions apply. Bet must win to receive bonus bets which expire in seven days. Minimum odds required. For additional terms and responsible gaming resources, see DKNG Co Audio limited Time offer.
Interviewer
When you talk about the crazy pressure involved within Living Color, was it in all of the other spots? The Daily Show? The doing of a Daily show must be really hard.
Larry Wilmore
Well, the Daily Show, I only would come and do my bit. So I wasn't involved in that time. Time I was still here in la, you know, working on shows and stuff. But, you know, running the Berry Mac show is very difficult, you know, when you're having to, you know, I created this show and you're running it and all that. I famously was fired from the show after winning an Emmy, Peabody, every award you could win, you know, because that was at odds with the.
With the network and everything. We're kind of fighting over what the show was. And that was a huge battle that took a huge toll emotionally because I, you know, during that time, I felt myself getting into a bubble. There's nothing I could do about it, you know, and that kind of crashed my bubble at that time. I'm looking back at it now Knowing that at the time, I didn't know.
Interviewer
You know, take me through what was happening there, though. That seems really pressurized. You've got a hit show and you've got all of the pressures. I'm imagining this. I don't know any of the details of white people telling black people how to make show when you've already got it successful and you've got a character that is going to be insistent upon being himself. He's not going. He's not going to be a clown for others.
Larry Wilmore
Right. It was very tough emotionally, and you felt like you were completely on an island alone in a lot of that, you know. But I was very lucky. There were people in showbiz who supported me from the outside and gave me a lot of emotional support, which was nice. Some very famous show creators and runners. And, you know, I remember running a Steven Bochko, who I had never met, but was a huge fan of, and he came up and hugged me because this was after I was fired, which is a very public thing, and said, larry, those assholes, don't worry about them. You know, I'm like, oh, man, that made me feel so good, you know, to get, you know, recognition from people, you know, my peers and people I respected and that type of thing. But it's very difficult going through that type of thing. And my marriage was tough at the time, too, and, you know, dealing with all those things emotionally and. And I definitely was getting in a bubble then, too, Dan, because I was getting successful, making money. And you start thinking, you know.
I don't know what the right word is for it, because it's. It's just. There's just a bubble of isolation where, you know, it can be harmful to you, I'll just say, you know, so ironically, it was one of the best things that could happen to me, I think, as a person, when that happened.
Interviewer
To be fired, I think.
Larry Wilmore
So, you know, when I look back at it, you know.
There was. In Living Color was one of those. Those bubbles in a different way. One of the things we did on the show, the. The show itself, working on the show was very toxic. You know, people talk about that Saturday Night Live because it's very competitive in that type of thing. And I could feel that toxicity, like, working its way in me. But you're in that bubble in the show. You think that's how we're supposed to act. But I could feel it. And, you know, when I left that show, it was almost like a purge, you know, and thank God I wasn't on it long? Two years was enough. Two years was like five years on anything else, you know, but. And it was such kind of a lesson to me even then of how fast that can happen to you. And it's not just showbiz. There's so many things in your life that can do that for you. So. So, you know, when I talk about being in a proper relationship with things, not defining yourself or making sure if you're in a bubble, to check yourself, you know, and look outside of that and that type of thing. And I do these things for.
Survival'S sake, not to be a philosopher, to figure things out. It's so I can basically survive.
Interviewer
So you could feel good or not feel bad?
Larry Wilmore
Yes, exactly.
Interviewer
So why did you get fired though? Do you know?
Larry Wilmore
Bernie Mac show?
Interviewer
Do you know now, like, what really happened?
Larry Wilmore
They never understood the show. So I was always in a fight with them and they didn't understand what I was doing. They thought I was incompetent. You know, even though the show was winning all these awards and the things that I did was on purpose. I actually deconstructed the sitcom in order to write that. Ken Kwapas, who directed the pilot, we watched French New wave films together to kind of figure out the rhythms.
Interviewer
They thought you were incompetent?
Larry Wilmore
Yes, trust me on this. In fact, I think one of them admitted that later and treated me like that too. I remember a famous meeting where a lot of the storytelling that I did was intentionally.
The rhythms were mixed up a little because I didn't want. I wanted to surprise people in different ways. Because I'll just go over this real quick. This is. This is kind of a writer nerdy thing. Okay. Just so you know, ahead of time. So when I created the show, I based it on some of the reality stuff that I was watching. I wanted to do a different rhythm that was on TV, which when think about the year 1999, year 2000, when I'm doing this, it's mostly multi camera sitcoms that are your comedies and television Friends probably being the biggest one at the time, Right. There were no single camera shows at the time. There were nothing. What you see now of these types of shows. So that didn't exist in television, right? So I wanted to do a show that had a different rhythm than what we were watching. And so there was a show called 1900 House. It was a documentary, a pseudo documentary about this family that had to live like it was 1900, they were in England. And it was fascinating to me, you know, and there were cameras Kind of just put in the house, kind of observing them, right? And, you know, and their behavior changed their relationship.
Interviewer
I'm just laughing at the creative inspirations for the Bernie Mac show. Like, it's like, no wonder they were confused by the language you were using. That's true.
Larry Wilmore
So, you know, I just saw behavior change, and I love behavior is one of my favorite things to observe. You know, relationships get redefined and how it change people. And they have this confessional camera at the end of the week. You could go and talk about your sins, you know, and say, I had a Snickers ball today. I wasn't supposed to have it, but I couldn't help myself. You know, I'm dying in the. You know, like, this is fantastic. This should be, like. I should use this as a storytelling technique. Maybe I should put some cameras in it in a house and just see, like, we're observing a family rather than the action being pushed towards us. And as a theater major, I studied playwriting and all that stuff, you know, so a lot of different forms of writing and that. I always try. I like to play around with form and that type of thing. So I. I was approaching the idea from a technical standpoint at first. Then I saw Kings of Comedy. I went to this special screening, if it hadn't been released yet, and I saw Bernie talking about his kids. And I'll hit. I think you should be able to hit a kid in the stomach, in the throat, you know? And I was like, oh, my God. And I. Like. I said, oh, if I put Bernie in a house taking care of his sister's kids, we're emotionally drawn in. I said, that's a. Because I knew I needed a compelling reason to watch it. It just couldn't be a family. What's the compelling reason? I'm like, that's a good emotional journey to take the audience on. But we're just observing him doing this. So that's how I started with the show. I pitched it to Bernie, and he loved it and pitched it and got it made. But then I had to write the damn thing.
Interviewer
You didn't tell him anything about this French stuff? This 1900s French stuff? You kept that out?
Larry Wilmore
No, no, no, not at all. Not at all. But he got the gist of it. But just because I came up with it didn't mean I knew how to write it. There were no examples of anything like that I could draw from. So all the things I learned about a sitcom, I had to kind of throw out. And so I swear to you, man, I spent. I had a deal at Disney at the time. It was one of those just writer deals. They just keep you there hoping it'll come up with something. It's like a two year deal. My deal was over, but I kind of stayed in my office and I didn't leave. And I would.
Interviewer
You were Milton from Office Space.
Larry Wilmore
Exactly. And so I would just drive in the lad. Hey. You know.
And I would be in this office and just kind of hiding. I swear to you there was the way that I pitched the show. I knew it had different rhythms and everything, but I didn't know how I was going to write it. But I knew it had to be different. I wrote the same three pages. I couldn't get past page three for four weeks. And sometimes I go to the commissary and I'd be, be. I'd be. I'd feel guilty, I feel sad. I'm like, why did I pitch this thing? It's unwritable. I can't write this thing. You know, what am I going to do? You know? And I was almost ready to almost get. And I was ignoring calls from the, oh, you know, when are we gonna get an outline? I can't give him an outline. I don't know how to write this thing yet, you know. And so just really just hiding out in this office I wasn't even supposed to be in. And then about four, a little after four weeks of doing this, can't get past page three. I looked up at my laptop and I was on page four and something broke through. I got it all of a sudden and then it just poured out of me, you know.
Interviewer
So it is possible. It is possible for it to just be free flowing.
Larry Wilmore
Free flowing.
Interviewer
You said I'd be doomed for the rest of my life. I'd never.
Larry Wilmore
It is possible. Still a prisoner of the thing. But I got it poured out of me 36 hours, the whole thing. I suddenly got it. And that. That script basically won me the Emmy later on the. That thing. But I got it. What I got was there was a certain aspect of it that I had to free myself up. And the. And this is what I said in a nutshell. And the basic aspect of it was this can't be a plot driven story where A happens and then because of that, B happens. And then at the commercial, what's going to happen because of A and B? You know, I was watching the Real World because it was, you know, at the time, one of these shows that I was kind of drawing from. And at the Commercial. There wasn't a plot type of thing. It just went to commercial, you know, and then we come back and it just started up. But there was no manipulation at the commercial. And I kept playing back and I'm like, how come I want to come back? I'm like, what's going on here? There's no plot manipulation. Why do I want to come back? Because I wanted to ape the feeling of that. And it just dawned on me and I thought, you know what? I just want to know more of their journey. I just want to see more of it. And that was. That broke my heart.
Interviewer
Well, you had Bernie Mac.
Larry Wilmore
Yes. And I thought, it's enough to just want to see more of the character's journey. There doesn't have to be a plot manipulation. And so that broke my head.
Interviewer
These characters, though, when you're talking about the Wayans brothers and Jim Carrey, when you're talking about Bernie Mac, when you're talking about Jamie Foxx, these are all cheat codes. You're talking about the most talented people that there have been in the business.
Larry Wilmore
Right, right, right. I agree.
Interviewer
And so, yes, put them on television and figure it out.
Larry Wilmore
Yeah, so me. Yeah. So to that point, I want to put Bernie in a situation we haven't seen before, but the trappings of it are a bit invisible to the audience. I know what it is, you know, so.
So what I did was now the show was about Bernie's emotional journey. So the question isn't like in a plot driven episode of the pilot of the Bernie Mac show, the central question is Bernie gonna lose the kids they just got. That might be the question. And the plot might be he does something and then this happens. Maybe one of the kids runs away or. And then they come by and he's gonna lose the kids. And that's in jeopardy. And we're always thinking of that. No.
In an Emotional Journey episode, which is, I wrote, Bernie understands what it means to be in the position that he's in. He's different emotionally at the end of it. So there's virtually no plot. We're just following him during the day.
Interviewer
But this is all. And this all ends up with them thinking you incompetent, Correct?
Larry Wilmore
That's correct. Because they didn't know how to give notes to that, you know, So I became the incompetent one. So I remember there was this meeting where the head of Fox at the time was trying to lecture to me in front of everybody, trying to embarrass me. He said, well, the way you write things Is you bring something up in the first act, and you come back to it in the third act. And he's, like, nodding his head, and everybody's nodding their head. And I said, okay, so what you're saying is the way that I write is surprising? And he said, yes. I said, and I think that's a good thing.
Interviewer
And you're fired.
Larry Wilmore
I said, it's. You're saying what I do is unpredictable, right? He said, yes. I said, I think that's a good thing. So that's kind of the fights that we're.
Interviewer
And we think you're incompetent and.
Larry Wilmore
Exactly. But I was writing emotional.
Unpredictableness to make up a word, which was different than plot unpredictableness. Like, not what's gonna happen, but where are we? You know, where is this character? So now too much heart. More shows do that now. Now it's a given. Look at the bear. There's no plotting the bear. You know, those are emotional journey shows, you know, but you couldn't do that.
Interviewer
It stinks, though. To hear you talk about something that was so different, so good, and to say the experience stunk.
Larry Wilmore
It was. It was terrible because I was on an island, you know.
Interviewer
But you always have been.
Larry Wilmore
It sounds like I always have been on an island, but I don't care, you know, for most of it. I really don't, because it's more, like I said, figuring the thing out is what gave me the joy. And Bernie was fantastic in it. He was great, you know, And I would get calls every week from writers saying, oh, my God, that episode was fantastic, because nobody on TV was doing this type of stuff, you know, the type of attention that we got and everything, too. So it was frustrating that they didn't understand it. But what are you gonna do?
Interviewer
How much of your identity got tied up in that?
Larry Wilmore
I see a lot.
Interviewer
So you didn't have the healthy relationship at the time with show business. I mean, you're creating a wildly successful thing that's getting applause and it's running into the thing that Chappelle would run into when he would go to South Africa because he didn't want to do it anymore.
Larry Wilmore
No, it was terrible because I was tied in. Yeah, you're right. My identity was tied into it at that time, and it was devastating to get fired. You know, I was devastated by it, you know, and I had to learn the lessons that I had taught myself. All then I had to get back to that, you know, so that's why I say, ironically, it might have been the best thing to Have.
Interviewer
Well, it's crazy to hear you say that, because I'm guessing you spent months, if not years, rummaging around in how unjust that must have felt.
Larry Wilmore
No, not for long. I let that go right away. In fact, in the press, I was very. I took the high road. I said, well, we had creative differences. I was creative and they were different.
Interviewer
You know, that's not the high road. How is that the high road?
Larry Wilmore
It's the sneaky high road. It's the snake.
Interviewer
That is not the high road. No, it's clever. It is. I'm not disputing that it's clever. I'm disputing that it's the high road.
Larry Wilmore
I pretty much let it go. But I did an interview two years ago, was it, for Vox, where I got to really lay it out clean. And so the last few demons of it were fine.
Interviewer
Well, I would imagine. I would imagine that it would be scarring in a way that would be imprinting, because you arrived at wild success over all the obstacles, and you were the creator of that show. Like, you weren't just someone in the background. You were a founder.
Larry Wilmore
That's exactly right. Yeah. It was devastating. It did take a while. And that's. After that, I decided to go back to performing because the reason why I became a writer and producer in the first place was to hopefully create my own show that I could do, because I felt Hollywood didn't get me at that time. So that was kind of my journey. And it took me. That was another thing that I had to remember. Remember why you're doing this, Larry. It's so you could create a space for yourself that didn't exist, you know, and so I got back to that a couple years later. I was on the Daily show, you know, doing that stuff. And so I got back to my roots of what I really wanted to do, you know, so that's what I mean. Had I not gotten fired, I never would have been on the Daily Show. I never would have done White House correspondence standing for President Obama. You know, I never would have. I probably wouldn't be talking to you now. You know, I wouldn't have this opportunity to reach people in a different way, because I just would have been a showrunner during that time. I don't think I would have done that had that not broken apart in the way that it did. And it saved me as a person, because that's another bubble that's very dangerous, you know, that. You know, at least it is for me, you know, who would have been, you know who was getting caught up in that type of thing. But it is for a lot of people, you know.
Interviewer
Have you felt much that felt like that kind of hurt?
Larry Wilmore
No.
Interviewer
Where does the White House Correspondents Dinner rank in terms of career achievements that you can possibly imagine?
Larry Wilmore
It's pretty high. I manifested it, first of all. It was something that as soon as Obama became president, I said, that's what I want to do. And I ended up up hosting the Congressional Correspondence Dinner a couple years later. I thought, okay, well, maybe that's the closest I get. He wasn't there. And I made jokes about that, and I was fine with it. And then when I got that, I was like, this is crazy. I put that out there, you know, and it actually happened. It meant so much to me as a person that he was president during that time.
To do that was huge. It really meant a lot. It was beyond politics and all that stuff. It was just a personal, cultural thing.
Interviewer
What else. Would you. When you say it's pretty close to the top, what else would be up there with it, like, in terms of just proud of yourself for career achievement? That is a place that you just never imagined you would arrive with. With, you know, spurred by the fuel of your creativity?
Larry Wilmore
Well, I would say the top things, of course, the Burning Mac show, because of what I described to you doing that, that and probably the Nightly show, you know, because that was another very, very scary thing, you know, not knowing what it was. Having fever dreams days before we're going on, because I'm not sure what the show is, you know, all that type of stuff. And finally thinking I figured it out and just putting it all out there every day, you know, so very happy that I did that and able to get it.
Interviewer
All of them pressure cookers, though, right? All of them things that you're afraid of, like you are not dancing with a parasol through anything of this stuff. All of them are, like, hard but fulfilling. Very hard and anxiety inducing.
Larry Wilmore
They're all the hardest things I've ever done. All of them, yeah.
Interviewer
Are there any easy things that you've done that have resulted in.
Larry Wilmore
Ironically, the acting stuff is the easiest, you know, and it's been some of the most fun, but it's not been the most fulfilling. Ironically, it's challenging enough.
Interviewer
It's plenty challenging, but it's not this kind of challenging, this suffering, hurting, you know, acting. You're, you know, waiting for 13 hours.
Larry Wilmore
To go to them. I feel like I'm playing like I'm getting away with something, you know, which is Fine. And it's great, and I really enjoy it. Not to shit on or anything, but I really enjoy it. But it's just different, you know, I feel very fortunate in some of it. I've worked with some really great people and that kind of stuff, you know, as a performer. But it's funny that stand up was hard, you know, that in terms of performing, standup is the hardest thing to. To do. And I'm starting to do stand up again. And once again, it's hard to construct that. And you really only want the audience tells you what's funny. You don't tell them, you know, so you only learn it on stage. So to go through that again right now is kind of interesting fun.
Interviewer
I promised this earlier, and sometimes I end up wandering and never get back to it. But your first two shows, your first two standup shows, the first one was a wild success. The second one was a terrible failure, correct?
Larry Wilmore
Yeah, that's true. True.
Interviewer
So take me through. So the first one, you get the feeling of knowing, I want to do this. This is for me.
And then what happens with the second one?
Larry Wilmore
Well, this is very early on. I was like, maybe 17, you know, and I go to the Comedy Store, and I didn't know what I was doing. I didn't have it. I was doing impressions, and I think I was doing a memorized routine, you know, from some record or something like that. I mean, it was so raw. It's like doing a talent show at a high school was my approach, not as a professional comic. And so looking back, it's shocking that I got laughs on the first time, but I think my confidence got me through and everything. Audience were like, you only do three minutes, you know, and. And then they, you know, brought me over. Oh, that was great. You know, we'd like you to come back and showcase for Mitzi was at the Comedy Store. And I was like, yeah, great, you know, And I'm like, right now? And the day that I had to go showcase, I was sick as a dog. Just sick as a dog, you know, And I said, but I gotta go do this. And I just felt differently on stage. The light that happened the last time, there was none of that. No connection with the audience. They could care less what I was talking about. It was the complete opposite feelings, you know, of everything that happened. As great as it went the first time, it was the complete opposite. You know, I come off stage now, nobody wants to be your friend.
Everybody wants to be your friend. The first time on an island again. Oh, man, it Was terrible. I have a Daily show story about that, too, that's similar. But nobody wants to be your friend, you know.
Didn'T. Of course, I didn't get called over, didn't get asked back. And I thought I had just failed to go back to your original.
Interviewer
Well, you also fled comedy for a while, did you not? Did you not go back hiding the easier thespianism?
Larry Wilmore
Absolutely. But keep in mind, though, you know, walking around the halls of the Comedy Store back then, people like Richard Pryor, you know, I mean, even David Letterman, people didn't know who he was, you know, because I would sneak in there and watch shows and stuff, you know, it was very intimidating. Who am I to think that I could just do this? So I wasn't wrong completely, too, you know, of like, nah, Larry, you better dial that back a little bit. You know, But I knew nothing about the form or anything. I didn't know. When I eventually went back to it, I really knew more about it. I knew you had to write jokes, you had to write an act. You know, many people do well the first time, and you die your second time, but you just got to keep doing it. And then after a while, once you start to have an act, that's the thing that works, not so much just being funny. So I just didn't know the technical aspects of it. I just didn't understand it. I was just too innocent.
Interviewer
Before we get out of here, I did want to talk just politics with you briefly. You must find great despair and how dumb everything has gotten. No.
Larry Wilmore
Well, dumb. What do you mean when you say dumb?
Interviewer
I mean when you're talking about. People are in their bubbles, and so it's not political discourse anymore. It's not disagreement about, you know, nuance and discerning philosophy. It's a different set of facts that two sides are choosing.
Larry Wilmore
It is disappointing.
Interviewer
You don't think it's gotten dumb?
Larry Wilmore
Well, I. I may discreet the word gotten, you know, not the word dumb.
Interviewer
Okay, maybe it's just. Maybe I'm just new to how overt some of this stuff is because it seemed to be hidden better from me. I'm not. I'm not politically astute.
Larry Wilmore
I know what you mean. Like when people. Well, I just remind people that Caesar was stabbed on the Senate floor. You know, I mean, like, politics has been nasty for a long time and that type of thing. It's just, you know what? So much of it, so much, at least decorum has just been thrown out, and that disappoints me a lot. You Know, because at least when I was coming up, people could disagree with each other, but there was kind of a decorum of how things were done that people at least respected, and that's just going away. And I just worry about that because it's. To me, it's like, well, will other things go away too? You know, just respecting of. Of the Constitution and all these types of things. Are we slowly chipping away at that? I don't know. And that just worries me a lot, you know?
Interviewer
So Black on Air, do you want to tell people what that has meant to you, what it is to you, or. We've got a deck of cards here, too, so we're great. So at the very end of this, we're going to put the punctuation on this, where you're. You're going to. To amaze people and make me feel awe, wonder, and discovery like I haven't since I was a child.
Larry Wilmore
See, there you go. What a surprise.
Interviewer
But congratulations on Black on Air and the fact that you are doing an interview show that is following all of your curiosities.
Larry Wilmore
Oh, thank you. Yeah. So Black on the Air, the podcast that I've been doing at the ringer since 2017.
It'S great. You know, it was allowing me to keep kind of engaging with the audience after my show, the night the show was canceled.
And I've been able to interview so many interesting people over the years.
And it's just been great. It's been a lot of fun. The show's coming to an end. The end of December is the last ones that we're doing, but I'm gonna be doing something again in that space. I still haven't figured it out. There are a couple of things I'm thinking about, but it's been great. I really enjoyed doing it, and it's just been a good run.
Interviewer
You stifled what felt like a bored burp in the middle of what sounded like profound indifference while talking. A passion. Talking about a passion project of seven years. Like, you really just sort of petered out there. There was nothing. I didn't feel much inspiration coming from you. It might have just been the stifled burp that disoriented me.
Larry Wilmore
Well, what is it you would like to know?
Interviewer
Oh, I just wanted to know what it means to you as a project. I don't know how many projects you've done done for seven years.
Larry Wilmore
Well, it's always been in kind of a pocket thing. It's not really a passion project, I would say, but it's a grateful space, if that's a way to put it. I feel grateful to be in that space and being able to engage with a lot of people, but because it's been on the side, I never really put all of my energies into it. Like, I've done other things. So maybe it probably hasn't been the blooming flower that maybe if I. If that's all I was doing, it possibly could have been.
Interviewer
Well, many people are going to be disappointed to hear if they're tuning into this because they want more Larry Wilmore and they want more of his personality as opposed to somebody who's just curious or being an interviewer who's a very good interviewer. They're going to be wildly wounded by the fact that you are and that the show is coming to an end, that you've just given them news that will be hurtful to them.
Larry Wilmore
The show is coming to an end, but I, doing a podcast, may not be coming to an end. I just haven't figured that out yet.
Interviewer
Okay, let's bring in the cards here so that I can get some wonder and discovery here. Yes. This is the amazing thing that we've been able to do.
Larry Wilmore
Have these even been opened with a crack stack? I'll let you open them just to make sure there's no funny business.
Interviewer
Okay. Okay. So this is.
Larry Wilmore
And we have a camera here. I can make sure the camera.
Interviewer
But what funny business could there possibly be?
Larry Wilmore
I don't know. People could think something. Oh, he's using his teeth here.
Interviewer
Well, I'm gonna spend a good amount of time trying to get these open because I don't have any fingernails. I won't accuse you of funny business if you want to try it.
Larry Wilmore
Let's see if there's a thing here.
Interviewer
It looks like this is where the whole thing is gonna come apart, where people are gonna see that you're cheating. And obviously the wonder and discovery is just gonna be two bit Hacker room.
Larry Wilmore
Oh, can I use your pen?
Interviewer
Yeah, I probably could have done that.
Larry Wilmore
There we go.
Interviewer
We're two. A couple of great magicians here trying to just open a deck of cards.
Larry Wilmore
I know. That's the trick.
Interviewer
How do you do that? It.
Larry Wilmore
All right, let's try something here. Let's take a look at these cards. You guys can see. What are these? Hollywood. Look at that. You guys can see. Let's take out the aces. How about that? Let's do something with the aces.
Interviewer
I love that we just sent somebody out. I'm assuming they didn't find it anywhere in this building that somebody had to rush with an hour of time to get this done.
Larry Wilmore
Well, you know, it's not prepared too. It just. Great. I want to make sure we can see here since we've got the video happen. Can you guys see that? Pretty good. We got the ace. Dan, I'm going to need your help in this, actually. I'm just going to need you to put your hand out like that. Now, here's the thing. This isn't really a trick these days, is there? It's really a couple of questions, you know, the first two are real simple, but the last one is a little tricky, so you have to pay attention. Okay, you got it.
Interviewer
I. I feel like what's going to happen at the end of this is that we are going to turn over a card that is the black astronaut we were talking about earlier.
Larry Wilmore
Wouldn't that be amazing? Okay, all right, let me make sure I get here so I want to get in the right position. Okay, Everybody can see this, right? You see? Okay, first two, real simple. What is the color of this ace?
Interviewer
Black.
Larry Wilmore
Wrong. African American. That's okay, Dan. Take your time. That's my. Oh, that's my bad. I should have explained.
Interviewer
African American is what I should have been. The color of that card is African American.
Larry Wilmore
I should have been clearer about it. Okay, all right. Everybody can see this. Okay, all right, once again, what is the suit of this ace? And keep in mind, I'm still a little sensitive from your last answer. Answer? No, no, don't answer that. It's a horrible joke. A horrible joke. The young guys don't even understand that joke. That's what's interesting. I think. I think he's old enough to get that joke, though.
Interviewer
Okay, I don't want to reveal that I got that joke. I want to keep.
Larry Wilmore
No, it's great. I can see your laugh. I can see your laugh that you get that joke. Here's a tricky question, though. Here's a tricky question. Which ace should be on top? See, that's a tricky question. Ace of spades or the ace of clubs? Should be. That's why it's a tricky question. Which they should be on top based.
Interviewer
On what you just did with my hand. Right? Ace of clubs.
Larry Wilmore
It should be the ace of clubs. You didn't see me switch it.
Interviewer
I did not see.
Larry Wilmore
I switch it for the other ac. That's the ace of hearts, see? And that's the ace of diamonds. It can't be these two, Dan.
Interviewer
It's neither one of the African American cards.
Larry Wilmore
Come on, man.
Interviewer
Larry, thank you for being on with us. Are you going to give me another one? You said that's it. That's another.
Larry Wilmore
This is your. I was going to spread them out, but they didn't. Yeah, there you go.
Interviewer
They haven't been shuffled at all. That is a clean deck. You're going to take it with you and you're going to have the regret that you didn't bring your own cards. This was the day that somebody asked you. You've been doing it daily for how long? Since you were seven.
Larry Wilmore
I know. What was I thinking? Yeah.
Interviewer
Larry, big fan of you and all of your work. Thank you for spending this time with us.
Larry Wilmore
I appreciate you having me on. It's been an honor. Thank you so much.
Commercial Announcer 1
All right, guys, the holidays are here. We got Noche Buena down here in Miami. Super important, by the way, which means a lot of my favorite memories start the same way. Ooh, an ice cold Miller Light. I crack open the middle light, look around at the friends and family, think, yep, we are definitely in the prime time season of the holidays. Whether it's a late night hang after the holiday party or standing around a fire pit with the family or like a Hajina, Miller Light just fits perfectly. It's the taste you can depend on. Brewed for flavor with simple ingredients and malted barley. Rich balanced toffee nuts. I knew you were going to show up and I was telling the people about the Kaachina and we can share this mic if you want to come over.
Larry Wilmore
When I hear, I just walked by, I heard you talking about Miller Light. I'm like, I need it on this. It's the weekend and it's time for.
Commercial Announcer 3
The boys to have a Miller Light.
Commercial Announcer 1
Exactly right. Chris is going to have a Miller light in about 20 minutes.
Larry Wilmore
5 o' clock somewhere.
Commercial Announcer 1
5 o' clock somewhere, baby. Miller Light. Great take taste. 96 calories. Go to millerlight.com beach to find delivery options near you. Or you can pick up some Miller Light pretty much anywhere they sell beer. Tis Miller time. Celebrate responsibly. Miller Brewing Co. Milwaukee, Wisconsin. 96 calories and 3.2 carbs per 12 ounces.
Release Date: December 11, 2025
This South Beach Session features an in-depth, candid conversation between Dan Le Batard and Larry Wilmore, acclaimed comedian, television producer, writer, and magician. Broadcasting from the Elser Hotel in Miami, Dan dives into Wilmore's multifaceted career, his unique philosophy on creativity, career success and authenticity, and the personal history that shaped his worldview. The episode blends humor, vulnerability, wisdom about Hollywood, and even bit of magic.
[00:57–02:37]
[02:37–07:50]
[07:51–10:50]
[13:38–16:13]
[19:22–21:57]
[29:30–32:32]
[33:47–45:25]
[49:41–64:09]
[65:25–67:13]
[68:17–71:09]
[71:09–72:48]
[73:07–75:23]
[75:29–78:33]
| Time | Segment | |------------|----------------------------------------------------------| | 00:57–02:37| Wilmore’s professional identity; love of producing | | 02:37–07:50| Magic, childhood, and the pursuit of awe | | 07:51–10:50| Comedy influences, Flip Wilson, school experiences | | 13:38–16:13| Family challenges, emotional adversity, turning to arts | | 19:22–21:57| Defining success, key life lesson while selling books | | 29:30–32:32| Service, mentorship, life philosophy | | 33:47–45:25| Hollywood bubbles, fame, authenticity | | 49:41–64:09| The Bernie Mac Show—creation, innovation, painful fallout| | 65:25–67:13| White House Correspondents’ Dinner and other milestones | | 68:17–71:09| Returning to stand-up, lessons from comedy failures | | 71:09–72:48| Politics, bubbles, and accountability | | 73:07–75:23| Podcasting; ending "Black on the Air" | | 75:29–78:33| The card trick magic finale |
This South Beach Session with Larry Wilmore is a masterclass in candor, humility, and creative vision. Wilmore’s journey—marked by both dazzling achievement and formative failure—is rendered with humor and self-awareness. Key themes of service, proper relationship to career and fame, and a lifelong curiosity about both wonder and comedy, elevate this conversation beyond a typical interview. The episode concludes, fittingly, with Wilmore rekindling that lost adult sense of wonder—reminding listeners, with a grin, that there’s always magic to be found if you know where (and how) to look.
For listeners seeking insight into Hollywood, mentorship, personal resilience, and authentic creativity, Wilmore’s episode is both profound and delightfully entertaining.