As an actor, writer and comedian, Larry Wilmore has either created or had a hand in shaping so many iconic shows, from “The PJs” to “The Bernie Mac Show” to “The Office” to “Insecure” to “Black-ish.” He is currently an executive producer on the Hulu legal drama “Reasonable Doubt.”
How did his involvement with the show come about? “I had a producer deal at ABC Studios a few years ago, after I did ‘The Nightly Show’ (on Comedy Central) and I got together with Kerry Washington’s production company, who were developing a project based on Shawn Holley, the lawyer. It was going to be for network television and they asked if I wanted to help on the project.” That version of the show didn’t get picked up, but a year later the studio reimagined it for streaming and made the lead character a lot messier and more of an antihero.
Wilmore also has a career in front of the camera and when asked about a worst moment, he recalled his audition for “The Daily Show,” where he had the tongue-in-cheek title of Senior Black Correspondent.
My worst moment …
“This was kind of a transition in my career at the time. I was taking a bet on myself to do something different. I had just gone through a cringey moment a few years earlier when I had been fired from ‘The Bernie Mac Show’ very publicly. We didn’t get along over there. Even though I won a ton of awards, it didn’t matter. In fact, the press said that we had creative differences — I was creative and they were different (laughs). But up to that point I had been primarily behind the camera. I started my career as a stand-up and it felt like Hollywood wasn’t really getting what I was doing, so that’s when I started writing.
“After ‘The Bernie Mac Show’ and all that stuff, I was really at a low point in my career … and then went over to help with ‘The Office.’ At that time, no one thought it was going to be anything; in fact, people would say, ‘Oh man, ‘The Office’? You’re working on that thing?’ All of this is just context for where my career was at this point. I did a cameo on ‘The Office’ as Mr. Brown and once I did it I realized, oh, maybe I should start performing again. Maybe this is the signal to get back in front of the camera.
“And ‘The Daily Show’ to me felt like an opportunity to do something different in my career. So it was not just a normal audition, it was: OK, Larry, you’re doing something new here.
“I met with Jon Stewart (the show’s host at the time), it went great. And he said, ‘Let’s try this, I think this will be great.’ So we (Wilmore and the show’s writers) were writing a piece and we thought this guy could be the Black correspondent, and someone joked that maybe he could be the senior Black correspondent. That’s how that came about.
“But trying to find the right point of view was daunting. The people that had done it at that point — Stephen Colbert and Ed Helms — had very specific comedic voices and it was hard to get their voices out of my head. On the page, I knew I wanted my approach to be contrary to that.
“Keep in mind, I’m not going to audition for ‘The Daily Show.’ The way it worked was, I met with Jon, we talk and he said, ‘This sounds great, let’s try it.’ So my audition was going to be on the air! Very nerve-wracking. Jon has us write two pieces and he said, ‘We’ll air one tonight and we’ll save one to air next week.’
“So first we do the rehearsal and the crew are there and the writers are in the audience; people wanted to check out the new guy. And let me tell you something: There was not one laugh. It was the death of comedy. I could tell as I was doing it that it felt awkward and stiff.
“This was around the time John Oliver had just started. Rob Riggle had just started. Aasif Mandvi had just started. There was a whole new wave of correspondents who were coming in, so people were excited: Oh, here’s another new person, who’s this gonna be? And that excitement completely went away during that rehearsal (laughs). You could just feel it drain from that room.
“So I finish the first one and I’m like, ugh, good lord. And then we do the second one and it’s worse. I mean, it’s just creaky. And I’m thinking: Larry, everything you thought this could be is disappearing! This is terrible!
“I’m completely panicking. I’m probably flop-sweating by that point. You know how you don’t name a farm animal because you know you might have to eat it one day? It was that energy. Nobody was looking me in the eye. Nobody wanted to get too attached. People were being superficially nice, like: ‘Well, good job.’ But it was very hollow.
“And now I’m waiting and sitting by myself and I have to tell you, it was the loneliest moment ever. Fired isn’t even the word — you’re not gonna make it on the air (laughs). My confidence was completely shaken and it’s the lowest moment you can have as a performer.
“Meanwhile, someone calls me in and says, ‘Jon wants to see you,’ and it feels like you’re being called into the principal’s office. Here’s what’s playing in my head — I’m a writer so of course I have to write this scenario in my head. And it was: Jon sighing and saying, ‘We appreciate you coming by, but it’s not going to work out. But hey man, thanks a lot. Good luck.’
“So I go in there, and he says: ‘We decided we’re not going to do two bits, we’re just going to do the one. But let’s go through and rewrite it and put it in our own voices.’ So I felt a little better, but I was also like: I hope I don’t screw this up.
“Jon is brilliant at this, cutting out the fat. But also we were able to kind of ad-lib back and forth and have more fun with it and it became a little more conversational, rather than written. So we finish and I’m still not feeling good. Like, what if this bombs in front of the audience? I could be committing to a parachute jump without a parachute (laughs) with Jon looking out of the plane like, ‘Thanks, man! Appreciate everything!’
“It’s so scary. It’s the scariest moment you can have as a performer. I was going out knowing I had bombed the death of deaths during rehearsal, and sure, we did a rewrite, but it’s still basically the same piece. And you start thinking: Maybe I’m not funny. Maybe I made the wrong move here. Larry, why did you even come to ‘The Daily Show’? Who are you to tell Jon Stewart you think you’re funny (laughs). And at this point, I’m already an Emmy Award-winning writer and producer and all that stuff, and here I’m at my lowest point because as a performer, your ego gets crushed instantly.
“So that’s my state of mind right before we’re about to shoot it. Then they take me out to set and I see the audience going, ‘Who is this guy?’ (Laughs)
“And then Jon did the best thing you could ever do for a performer. I’ll never forget this. This is the generosity of Jon Stewart. I think he could tell I was nervous and he looked at me and he says: ‘Hey man, just look in the camera and just effing give it to America.’ And that really relaxed me when he said it. Like he was on my side. He wasn’t neutral. It was the nicest thing he could have said, because as a performer I could relate to that, as opposed to ‘good luck’ or ‘break a leg,’ you know? Just give it to them, man.
“We come back from commercial, he introduces me and the first joke gets a laugh. And here’s the thing: Once I get a laugh, now my instincts as a comedian kick in and I go, oh, I got a laugh! And now I’m just hitting it as hard as I can and I ended up killing, it got such big laughs. And now the crew is like, is this the same guy who was at rehearsal? Can’t be the same guy.
“I’d had my writer’s hat on this entire experience, and this was when I finally put my performer’s hat on. We’ve heard enough from you, writer, you’re not leading us to the promised land (laughs). Thank you for the start, I’ll take over now — I got this.
“I finish and I get this huge applause, Jon stands up and says ‘great job.’ I was completely on top of the world. It was so much fun. And of course I was relieved too.
“And it changed the trajectory of my career.
“But it could have gone the other way so fast, and I never would have been heard from again (laughs).”
The takeaway …
“Trust Jon Stewart (laughs). Whatever he would have said, I would have agreed.
“And by the way, I don’t even think Jon would remember that he said those words of encouragement. He was just being who he is. But for me as a performer, that was the best thing anyone could have said.”
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