Inside Late Night with Mark Malkoff - Inside Late Night: Roy Wood Jr.

Episode Date: October 28, 2025

This week on LateNighter's Inside Late Night podcast, comedian, host of CNN's Have I Got News For You, and author of the new memoir The Man of Many Fathers, Roy Wood Jr. joins Mark Malkoff to talk late-night breaks, near-misses, and knowing when to walk away.Make sure to follow us on social media (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@latenightercom⁠⁠⁠⁠⁠) and subscribe on all podcast platforms and YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@latenightercom⁠⁠⁠⁠⁠ to never miss an episode!

From late-nighter.com, it's inside late-night with Mark Malkoff. Hey everybody, John Shider here from Late Nighter, getting you set up for what you are about to listen to, which is a fantastic conversation between Mark Malkoff and Roy Wood. Jr., who you may know from his time as a correspondent on the daily show, but he is now the co-host of Have I Got News for you over at CNN, and he has a new memoir out now, the man of many fathers, and this is a fantastic conversation between Mark and Roy Wood Jr. So without further ado, here's Mark. Roy Wood Jr., nice to see you. Thank you. Thank you for having me on. How the hell are you? I'm doing well. I'm doing well. So you are scheduled, by the time this airs, it'll be over,

but you're scheduled tomorrow to go on Jimmy Kimmel Live. You've been on before. How do you prepare for a talk show appearance? Have you just been jotting ideas down the last week? How does something like that come together? Do you have a game plan for tomorrow already? A little bit, but a lot of it boils down to current events. You want to see what's going on in the world and kind of have, for a show like Kimmel,

have an opinion or two about what's going on in the world. So, you know, for where we are right now, you know, we're in the middle of a government shutdown and that's starting to ripple out and to affect air traffic control. So, you know, maybe there's a conversation to be had about that. There's a peace deal in place. Maybe there's a convo to be had about that. Tonight, I'm moderating a book chat with the vice president, Kamala Harris, in Durham, North Carolina. Whatever happens there might be something interesting. You know, to bring about um so you know i don't know it's it it varies and then it can be something you know it could be silly and random you know when i was on kimball at the top of the year the fires were still happening in malibu and i ended up doing a ride-along with the lea county fire uh engine 16 down in compton and i did that pretty much for about a day and then was on kimmel the next day so i just talked about what I did and told the story of these firefighters who were covering like they were like it doesn't matter I spoke with really brave people and watched them do brave stuff from the

comfort of the truck while I ate a snickers um so do you ever since you have to do so many TV appearances and you're so busy do you ever employ writers for your talk show appearances to give you jokes no I know some comics do that they do not really my thing I understand why some do it, but I don't know. I've always enjoyed watching Bill Burr go on some of his classic rants and take things off the rails. So, you know, that's more fun. Like when Burr used to be on Conan. Oh, they were the best. Before he was really famous. Yeah. Yeah, he was, it was great. He still is very funny. I want to take you back to the Montreal Comedy Festival. This was, I think, 2006, 2005, possibly, but you'd only been doing stand-up at this point six or seven years.

Did you recognize that you had a killer set that night? Or was it one of those things? Because several late night shows wanted you because of that set. Did you realize that, or was it just a regular set that you didn't realize the impact I was going to have? I do. All of the jokes did what I hope they would do. Because Montreal was also my first time performing out of the country. So I was super nervous about, oh, Lord.

I don't know how this will translate, and I'm Southern, and I have a thick country draw. How's that going to come across up here? And, you know, I have all of these random jokes, and some of them, or at least I consider them edgy at the time. I don't know how that's going to, like, you're just in your head about how much of the Americanness of the bit is going to translate on another side of the country, but. You know, that new face is set, you know, it was good. It was one of those nights where, ah, everything's working. And as I'm walking off stage, I meet the Booker for Letterman, Eddie Brill.

He comes up and introduces himself to me. And three months later, I'm on Letterman, making my network television debut. And I feel like that's when I kind of figured it out. It wasn't at Montreal. I've had good sets before that lead to nothing. what does this worth? What does this mean? Whatever. I got a really nice write-up in the Montreal Gazette the next day about that set. But again, it's comedy. It's all subjective. But when I was on Letterman three months later, I was like, oh, that guy really liked me. Because I know it does not, the runway to get on late night as a comedic performer, nine to 12 months, usually. Usually, so to go from Montreal to basically right on the air, that was, that was pretty monumental.

Were you nervous? How were you before the show being backstage and working on the set? Letterman, I was petrified. I was petrified at Letterman. One thing that helped, though, is that the couch guest, the first guest before me that episode was Pete Rose and RIP to Charlie Hustle. but a little rude backstage to your boy. And he wasn't a jerk, but it was a little off-putting.

And that gave me just enough, fuck him, to forget about being nervous for my set. So in a way, Pete Rose Hill. The irony is that I got on Letterman in three months after doing Montreal, never performed on the show again. You never know. I mean, some of the best Johnny Carlin, person people, some of the best. You never know, some of the, on Letterman. But yeah, you had a good

enough set that all the other shows did want you. It's strange with Pete Rose, because normally when they're backstage at a show like that, they're on their best behavior. They might be jerks to the people that are waiting outside for Autaggress, but normally they're polite, but I'm glad that helps you. If I'm not mistaken, 06, Pete Rose was still on his Please Reinstate Me PR tour and still kind of like doing public appearances and looking like a regular guy and I guess hoping that would influence MLB to eventually, you know, reinstate him and Hall of Fame eligibility and blah, blah, blah. But no, it just, it wasn't, I've had worse interactions backstage, let me say, but it was one of those, oh, that's a guy respecting a sport I love. Oh, oh, that's your

energy. All right. Let me go figure out my jokes then. And, you know, I was still blue man and bright-eyed and thinking everything was beautiful. Like, anytime I did television, I was just always bubbly and friendly. And it just never, I tell a story, I told a story years ago about when I met Alonzo Bowden, who's to me by far one of the best comics working today. And I met Alonzo in the semifinals of Star Search on CBS. And because I come from a world of showcase comedy, which at the time was, you know, BET's Comic View and the Apollo and I think I'd done premium blend

at that point with Comedy Central, where we're just all here and we're comedians, being funny. How you doing? Yeah, chit-chat, backstage, chit-chat. And I go over to Alonzo Bowden, and he's not rude, but he's just in a zone. But I took being in the zone is rude. Because I didn't understand, this is competition comedy, bro.

You have 90 seconds. You have to nail this performance. There's so much riding on that 90 seconds, and I'm just walking back to, oh, we're having happy. And went out there and got my ass handed to me, and Alonzo went on to the next round. it was like it would be years later when I started doing last comic standing and then the happy chipper youngens would come up to me and then I'm kind of like shoo shooing them away a little bit all right man good talking to you I'm gonna go work on my set now yeah everyone's different with their process letterman needed quiet Johnny Carson could be behind the curtain just joking around but everybody's process whatever it takes to get you there do I have this right that your letterman set led to death comedy jam, which I had never heard any other comedian say before. They asked you to

audition based on your Letterman. Yeah, pretty much. I mean, there's like, there's a joke that I did on Def Jam that I also did on Letterman. Like, that was one of the weirdest things that I was proud of. Like, I know you're supposed to do a joke once on TV and it's, it's done. I've done it. But trust me, the people watching Def Jam, probably not watching Letterman. and vice versa. I'm a double down on this Mexican joke and do it in two places. Yeah, that was the letterman. The letterman stamp was, that was a good thing to have, you know,

in terms of what your comedic pedigree was at the time. Like, it was seen as, you know, a gold standard or, you know, within the industry or whatnot. And so, you know, I am a black comedian. I don't know if I'm always urban, you know, in terms of the topic selection or the performance style. But I think that Def Jam at that point, when they came back in 2007, was far more expansive because black comedy itself have become so many different things. I mean, Russell Peters was on my episode. Like, it was just a different feel.

You know, I'm sure there were non-black minorities in the old era of death. jam but probably not a lot probably not a lot um but yeah that was that was those were good times man um i do know for a fact i can't remember it's me chapelle and like maybe one more who have performed on letterman and deaf jam i never thought of that definitely the only one i'm definitely the only one to do it in a in a 12-month span yeah that says a lot that you can perform almost anywhere how did craig ferguson work out i know they wanted you from montreal as well you did that the year after you went on with dave yeah i mean you got a choice to do letterman or ferguson you have to do letterman because it's the earlier time slot it's the more legacy show ferguson was still kind of

fun in its legs and everything um ferguson was fun That was, the main thing I remember about Ferguson was that's when I learned about the concept of block shooting and how they don't shoot everything within the same, within the same day, per se. Like, I performed, it was me and, like, another comedian, and then, like, three music acts. And then I'm like, oh, yeah, it's going to edit together nice on the day. And it did. I don't even think Ferguson was there to see me perform. I didn't know that. Matter of fact, I'm positive.

The warmer back in the room brought me out. And then when it's time to tape the front half of the episode on that day, Ferguson was say, ladies and gentlemen, my guest tonight is a comedian, give it up for Roy Wood Jr. And then he just does a right-hand look to where I would be. But you watching at home, you're none the wiser. but you will never see me and Ferguson in the same shot. I didn't know that. I know Stephen Colbert for a few years on his late show,

the stand-up comedians, he would not be there. They would shoot four or five of them with an audience, and Stephen wouldn't be there, and they would do exactly what you're saying. That doesn't happen anymore. But, yeah, and then I know Conan loved you because you went on something like four times. What was it like with Conan?

Conan was great, too. Conan was probably the best because Conan's the only one out of all of those that I did twice or more than once. I did Letterman once. I did Ferguson once. At that point, I had not done Tonight Show. Leno's people, Tonight Show didn't really rock with me back in those days because you were either a Letterman guy or a Leno guy. Comedians weren't allowed to double dip between those two programs. So once you did one, your name is Sully with the year.

other, even though Letterman's not booking me anymore. I did Letterman 06. At this point, it's 2010. I hadn't done Letterman in four or five years. Tonight show still wouldn't touch me. But Conan did. When Conan left NBC and went to TBS and was building this new thing, Conan O'Brien, it's not stated enough what a champion he was of stand-up comedy and supporting stand-up comedians. I did Conan every year, I think, for four years. And every year, There were some times where that was my only televised stand-up credit. And that six, that five, six minutes on Conan was enough to get me into the colleges every year. I had a new piece of tape every year to promote myself.

Like, you know, there's a million stories about, oh, Conan's a good guy. Hey, that motherfucker kept me fed, bro, at a time where nobody else was rocking with me. I was ice cold in L.A. I didn't really have a good time in L.A. J.P. Buck, Conan, did the standup. He was wonderful. I worked with him on another show, but he was great with the stand-ups. So, yeah.

Funny J.P. Buck story. He was the Booker of Star Search that I did in 2003. Oh, with Arsenio was the host. And that's how I met him. Yes, J.P. Buck was the comedy booker for the Star Search reboot in 2003. And that's how he and I met. And then it boomeranged all back around because when Conan left NBC to come to TBS, he hired J.P. Buck. And the first person to call me to come do some comedy on Conan, it's J.P. Buck.

Yeah, because you were going to do Conan's Tonight Show, but then it went away. But you were all set to do the actual Conan Tonight Show. No one for time. Yeah, I mean, I was in the mix for it, but nothing had ever really, like he was on, he was on so short. It wasn't much at all. I think that was a four-month run. So, yeah, but no, I, you know, the Conan, if my memory is about Conan, it was about having the freedom to just do weird, different jokes and ideas. And, you know, when you're working with a talent booker as a comic, you're putting, you know, your best foot forward joke-wise. And then the talent book is going, well, here's the joke that are working better for this.

And so you kind of, like, you start with, like, eight to nine minutes of material. and then you kind of work together to whittle it down to here's the five minutes that will work best for this show and that's what you run with a year or two after you did Letterman you auditioned for the Daily Show did you really bomb

or are you exaggerating that when you went in the first time no no I definitely bombed I did not have a good audition it was not good and I know it was bad because the person who went in after me demolished. So if that be the case, then you know you sucked.

Like if you, oh, they're capable of lack. Because you leave and you go, well, no one laughs in an audition. They're evaluating these jokes scientific. No, they weren't. You weren't funny. Not only were you not funny, you left your car keys in the room. So you got to sit in the waiting room and, Listen to the person who went in after you destroy.

And was John Stewart there when you auditioned? Did you read with him? No, no, there was no John Stewart. It was just the producers. The producers know what John likes and what the flavor is. And I'm sure they probably whittled it down to a short list and took them those. And from that, they made the selection. But to get on the short list, I did not that day.

The person who went in the room after me was Wyatt Sinac. Oh, wow. Yeah. I'd say he had a pretty good run. on the show. Yeah, as you as you did. What do you think it was years later in 2015 when you got the Daily Show? What did you just chuck it up just to experience that you were more confident as a performer that you had done more television? I just hadn't acted enough. I was too focused on my lines that I was not listening to what they were saying. So I mean, even something as simple

as like when you hold your head and you're not like you're listening to the anchor, you're the quarter in the field. I didn't even do that. So the idea of like having emotions and difference, which, which changes how you read each line, it changes your performance. I just wasn't plugged in enough. That's all it was. And I fumbled it. The fact that I even got another opportunity is fucking wild. When you were there at the Daily Show 2015 to 2023, what are some of your fondest memories? If you could pick maybe one or two days from your run at the daily show where you're like this was this life is good i can't believe i this is happening um first day because we were live live across all paramount networks Trevor's first day September 28th

2015 we were live on like eight different channels and streaming live and like everybody was watching waiting to hate Trevor and that was a good day because we punched motherfuckers in the mouth um people don't like new things conan got criticized for a long time in the beginning anybody that's new a fresh face when they take over for an institution johnny carson wasn't instantaneous taking over for jack parr it took a little time but uh people wouldn't they replace somebody it's not the easiest uh transition for some people i would say um we did a video my first year at Daily Show called Black Trump, and we took all of Trump's quotes, and I sat with the writers and the producers, and we just laid every single wild and random thing Donald Trump

has ever said, like in the last five, 10 years, laid it out in a huge-ass word file, and just went through and created rap bars, and by the end of it, we got a rap song comprised entirely of Donald Trump quotes to establish that he just brags and talks shit like a rapper. And so we go, we record the song and I'm like, oh, this is pretty funny.

Trevor, somebody went, oh, that should be a video. All right, let's shoot a video. Well, if he's a rapper, we got to do it big. Next thing I know, a week later, we're at somebody's castle in Long Island, there's five Ferraris, there's 20 models, there's stacks of fake cash, there's jewelry, and I'm standing there in a suit and a Donald Trump wig with Jordan Klepper next to me as my Secret Service agent. I just remember turning to Clepper and just going, I went to college. I went to college to do. I went to college to do. this. I have a degree in journalism.

This does not feel journalistic, but damn, this is fun. That was a good day. There was a funny video, too, man. In hindsight, we did the video also when Trump was still Republican primaries, so the idea of him even being president was still, oh, that's silly. You'll never be, so you could laugh at him a little more. But, yeah, that was a, it was a 12-hour day, but it was fun. It was legitimately a good time, man.

Clepper was out there. He had broken his ankle or some shit. And he was out there in a boot. But they had like put like a sock over the boot to make it look like a dress shoe. So you couldn't even tell he was all fucked up. Power of television. It was a good day. In 2003, when you left The Daily Show, were you emotional about it? Was it one of those things where you're really sad or were you just ready to get out? I don't think I was sad In fact, I'm positive I wasn't sad It's just a procedural

It's a procedure It's nothing personal It's business Like I wasn't fed up with the show It's just All right I don't quite feel safe here in the long term

Why not? I should go Why didn't you feel safe just from a creative standpoint or how you were being treated? No, it's multiple factors. You have to think about your career in blocks, five to seven your chunks, right? At this point, I'm at the show eight years. Trevor already left the year before.

We're getting into this idea of the show needs a host, is my opinion. I don't want to do another year of guest hosts. or like so you know the the show there's a couple of factors one there's a merger happening with uh viacom and paramount and whatever the merger that finally happened this year that had been percolating for three or four years so i knew the merger was coming nobody knows when but you know it's coming well when there's a merger you consolidate costs so I'm running through every doomsday scenario of what will happen to the daily show, which is one of the most, it's one of the cheapest late-night shows to make,

especially with Trevor's salary off the books and a bunch of guest hosts a whole, you know. So we should be safe, but if we get a host, will the host want me? What if I don't like the new host? Will I be the host? Well, it's definitely not going to be me because, you know, y'all wanted to hire Hausson, but that fell through. And so when asked what's the plan for, you know, if it's not Hassan, then who? They go, oh, we haven't figured out what the new search will be.

Well, then I know at minimum it's not me. And I can't stay for another year of being considered when it's a presidential year. Because if there's ever a time to jump to a new show or find a new political satire thing to do, it's got to be during an election year. more often than not, the glut of new political, satirical shows that are introduced in the zeitgeist happened during election years. More so presidential than midterm. So if you look at 2016, 2016 birth, Sam B. and Wyatt Seneck had the puppet political show

for a while. You had the nightly show. Jordan Klepper came 2018 at midterms with the opposition. So you start looking at the birth of a lot of those shows And they're on the heels of elections So if my home is not the daily show Now is the time to leave So it's more so about

Sooner or later you have to leave the show That's what I feel Unless you're Keenan Thompson Unless you're Keenan Yeah She's Keenan working on the 50th floor of 30 right Like, the idea was if I'm going to land somewhere else, a presidential year's the time to land. If I stay here another year under what, and keep in mind, John Stewart was not in the discussion at that time.

If I stay here another year, then I'm done or they let me go or I'm a merger casualty because of salary dump. What if the daily show goes from every day to a week? what if what if the new host doesn't you do less or well if i ever want to experiment i should just leave now i wasn't angry it was just about when is the when is the window to do something else it really worked out for you i mean just to have your own show on that but i didn't know that but i give you a lot of credit i mean yeah but i can't even be eligible to be hired by cnn if i'm still under contract a daily show you're not allowed it's like the pros, you're under contract. You can't negotiate with it. Why will we let you do? Like, no,

that's not going to happen. So to even be open for the next thing, sometimes you have to clear your plate. Yeah, that's not always easy, especially, you know, you have, you're a father. It's more fun. You got bills. Yes. Yeah. But what's the difference, motherfucker? You're going to be in the same spot in a year. Yeah. Let me tell it. Let me tell it. merger happens you get cut new host doesn't like you you get cut too many guest hosts because they don't choose a host you don't like it so you leave all three of those scenarios have you out the door so when would you like to leave now at the beginning of an election cycle where you have a chance or in the middle of 2025 and since i left the show there's only been two new shows

introduced in that time it was us and after midnight and both of those our show is how about our news for you is based on a British show and after midnight it's is an extension of the Comedy Central IP you're right yeah never thought of that this nothing else knew has happened and both of those shows got greenlit in 20 motherfucking 24 never thought about that yeah was such an instant I mean it is still an institution in in England but yeah the two shows election years oh wow i never would have thought so it's like i don't know everybody thinks there's some divin because they didn't choose me as host and it's like well if i know i'm not hosting okay fine but now what am i going to do you have your own show so look look at what

you have now now that you have your own show you can pretty much do what you want is there anything that you would have done differently at the daily show if it was your show the way things were ran or the way that the creative was ran? No, not really. I mean, that show is already a machine. It's already like, you become the new plant manager of the factory. You're going to move the assembly line over here and then make the trucks. Like, you can change some of the ingredients, but the way the show is made every day.

I think the only real difference from host to host, like if you go back and look at the guest host episodes, the biggest difference was the angle of the punchline. The setup is the current event. And that remains that at the show, even under John Stewart, but the punchline and the moments of poignancy where you, whatever salient point you're trying to make about the issue, that's where you see the differences from host to host and person to person across late night, because we're all fishing from the same. media cycle. But, no, I don't think I come in and, I don't know, you changed the desk from a rectangle to a clear table. What visual aesthetic change can you make? I think there's probably more parodies or the types of joke vehicles we would use. Like, if you look like a big difference from Trevor to John, from John to Trevor, was that Trevor, because he was younger, he was more in tune with digital. The show eventually won Emmys for their digital work. And that happened under Trevor.

That never happened under John. And so that was Trevor thinking of new vehicles where you could take what the show does and still do it in different places. I don't know. I will say this.

I enjoy doing field pieces and if there was a way to do more of those on the show in a smaller, quicker capacity, that would have been dope, but I don't think that that was, for what it takes to make that show work, it's not your local news station where you just go shoot something real fast. It's good because there's a process and there's a lot of refinement that has to happen, which means there's a lot of people involved.

And so, you know, a lot of the things that I wanted to do probably required a degree of brevity that I would argue is probably reckless at that level. It's creatively reckless because you also want to make sure you're getting the points right. Because at the end of the day, that's why you're here is to try and make a point. So, you know, knee-jerk, no, I never really sat and thought about that. I never got pie in the sky about, well, if it's not Hausset, I know it's going to be me, because I did the correspondence. man i've i've i've seen i've set at a table with people who have looked us in the face and told us

our sitcom was coming back in a week later we were canceled i've worked radio jobs where i found out i was fired over twitter so this idea of employment in having some sort of emotional connection to it i don't know if i do I have a lot of friends over there. They know how to get in touch with me. It's not the end of the world. It's just business. You have a good attitude.

How did you get over to London to guest host, have I got news for you? Because it's this big institution over in England. It's been going on for decades. How did you become a guest host, and did you have any expectations? You want to talk about not wondering if you're the American-ish of your jokes. That's not important. You know, but the producers of the of the CNN version of the show are also the same producers of the London version. So they liked me.

They thought it would be fun to do a quick little crossover. And it ended up being a really good time. I'm terrible at pronouncing British words. So that's usually the main thing that kind of goes wrong more than anything else. but no they the producers in CNN they're like you want to go to london and host an episode i'm like if you want to see me butcher words i'll eat beans for breakfast in exchange for that cool no problem i want to get michael and amber out there i want to get my team captains out there they're so good together they work really well their chemistry is is fantastic

yeah they are group i mean yeah you're on season three you've done 26 episodes, 10 episodes a season. What if you learn from this process now having your own show versus, you know, being a correspondent on a, on a show and working in television for so long, but having your own show essentially, what would have you learned? I think hosting, I think being a part of a, being the, you know, kind of the head of the snake in terms of the face of the show. Um, there's a level degree. and care and concern for staff that you need to make sure you maintain and have because you're only as good as your crew on any of these shows.

So I try my best to shoot the breeze with the crew when I can. And I'm not always as good about having lunch with everybody because I always have some of the media thing going on or whatever. But more often than not, I really am just trying my best to just make the best show you can that week and then forgetting about it and moving on to next week. That's been the biggest thing is letting go of the joke you wish you did or a moment you wish you had a man. But when he said this, I should have said that. You didn't say it. And if you keep thinking about it, it's going to pollute your preparation for the following week. So I think you just have to let it go. You do the

best you can. You close your laptop and then you come back next week and do it and try once more. How much editing is there? You do the show at the broadcast center on 57th Street at CBS. After the show, how many minutes would you guess, if any, is it over? Are you a part of the edits? I'm not a part of the edits, and I don't want to be. Like, y'all have been doing this show for 30 years. You know how to put it together.

You know what stuff works within the show. I'd say they're probably trimming about 20 minutes fat Wow that's more than I thought That must be really hard It's necessary I don't give a shit

I'm home Like that's your problem figuring out which jokes You know a lot of it You know There's a couple segments We'll shoot Four things

And only use two You know And a lot of that comes down to, okay, do we want to keep the funniest two or the most poignant two? And then also, a lot of it also boils down to how stories evolve and change. You know, you could have a joke in there that, oh, Eric Adams, man, Eric Adams, him and Cuomo, the candidate, candidate, candidate. And then after you get done, Adams announces he's dropping out of the race. and you air tomorrow. We shoot the day before.

So between shoot to air, there could be something that happens that affects an entire chunk of the show. So you need that extra little a little bit of cushion to be able to get back up to the proper amount of minutes for broadcast. So yeah, not a lot.

Who are your dream guest to be on the show? You get a few. Ted Cruz would be fun. Gail King Not in the same episode But I think I think those two I think any sitting Republican

I think is a fascinating choice Just because you know you're not going to change their mind But maybe through conversation and jokes You can get a little bit of truth permeated into the minds Of one of their followers How much of the show In terms of what you do Is ad lib and in the moment

Versus prepared material everything you see on that show is pretty much 90% ad-libbed um the questions on the cards that's all just me asking the question to keep things going but if you look at what i do as a host nine times out of ten i'm just reacting to what's happening around me i'm not having a whole bunch of jokes on a card to only do the monologue style no you just keep it fun and light and the conversation will find you It really takes me back to, like, hosting this show gives me a new level of appreciation for Chelsea Handler and how she was able to do that for so many years on E talking about celebs with Chelsea lately. And so I just think that that part of the job, I'm very thankful for because, you know, I feel like as a host, it's my job to kind of be what people, what the viewer kind of wants in a way, which is just come catch up on everything that happened this week. And let's keep it light and fun and just informative.

I wanted to ask about your time in Florida. You graduated in 2001 from Florida A&M University. And I know that you did open mic in Birmingham at, I believe it was the Star Dome. And you were doing about maybe once a month initially. Were you really doing a five-hour drive from Florida to Birmingham every month just to do an open mic? I was doing an eight-hour bus ride. right, bro. I wasn't doing a drive. Eight hours, just to do an open

mic. That's a, that is dedication. I just I don't know. I just, I liked it. I don't want to perform in Tallahassee because I don't want to see people I know. I was wondering. Okay. Screw that. Yeah.

Screw that immensely. But yeah, that was, that was kind of my thing. It was just doing my best to crack whatever jokes I could and then get back to school. Probably did that. You know, I took the Greyhound down to Tampa.

I would go over to Jacksonville. I would go up to Charlotte. I took the Greyhound up there once. I was 19, man. I just wanted to get on stage. I didn't really care about anything else. How to open mics lead to you opening up for Tommy Davidson? You hadn't been performing that long, correct?

When it all happened with him? Well, by the time I got to Tommy, that was about a year, year and a half. It's not long. Somewhere in there. Yeah, but I mean, but I didn't tour with him. Like, I was the house and, like, I was the emcee at the comedy club. But it was a big deal because for the comedy club to trust you to open for Tommy, that's huge. That's a huge thing.

I thought he was going to take me to L.A. with him. I packed two months worth of luggage. He did not take me to L.A. with him. It did not happen yet. I read something that you said, one of the hardest audiences that you have ever faced was the amateur night at the Apollo. Can you talk about that? Yeah, yeah. I mean, it's black people doing their best to boo you.

But if you're good, you earn it. How did you do? The Sandman didn't come on when you were performing. No, but I almost. Almost. You're close. Okay. Yeah.

I came off stage early. Like I was, you're supposed to do three minutes at the Apollo? I did two minutes and 14 seconds because I knew the boo was coming. And I said, y'all not gonna get me. So I said, good night, walked off stage. Then you still have to come back on stage anyway for Kiki Shep for the audience judging. And they booed even harder. And I said, damn, you can't escape the boo.

What year was that? was that when you were still doing the day jobs like golden corral was it that when you did the apollo that was 2002 i'd already moved back home to birmingham i was interning at a radio station at a station i would end up hosting my own morning show ironically um yeah yeah that was apollo was easy to do though like you just submit your bits to the um you like you send like a tape of you, you mail it in, somebody watches it, they think you're good enough. You get the call. I got the call. And I was just going back and watching it, I was talking way too fast. I wasn't personable. I didn't greet the audience. I just broke every regular mechanical rule of public

speaking, not even comedy, just of general public speaking. So I didn't connect. you know but still returned years later to host the Route 100 so you know I've had a couple of moments of redemption on that stage just not televised yet yeah Apollo when you get your own radio show what is that your dad was a big deal in radio I mean in a place like Chicago I was reading an old newspaper article I mean they called him a household name um I mean he was doing a syndicated national column. It was one black man's opinion. For you to have your own radio show, what did that mean to you? It was, it was interesting. It didn't hit me two years later when I had my own child, but yeah, I had a morning show in the city on a station hired by people that used to work

for my father, nonetheless. So there is a legacy there. I don't think I necessarily loved being in his shadow early on just because you want to be your own man but i can't even imagine what that was like having your dad your dad was so fearless and so respected just to fill those shoes about what that would do yeah but keep in mind though i wasn't doing what he was doing my dad was a radio news journalist so he was a news reporter you know my pops went out and did interviews he held town halls he had call-in shows you know it was it was the whole gamut you know politically speaking and he covered a ton of like dangerous conflicts globally riots so he was respected for yeah so he was respected for a lot of a lot of reasons i'm the comedian doing prank phone calls

you know now by the time i worked my way up to host there is a different level of responsibility as the host of a morning show because in birmingham we were the community station we were the only morning show that was local in town and had locals on the mic so that means when certain things happen in the community we had to be the pool pit for conversation that show would turn into a barbershop real fast that show would turn into a place for actively local activists to come on and talk about. So in a lot of regard, you know, I became my dad

in a way where I just, you know, allowed my show to be a megaphone for people that had, you know, things of worth to say to people. But yeah, that was that was, that was a, that was an interesting time,

you know, to kind of be in that shadow. I am I always being in his shadow, especially in Birmingham. But I think all in all, you know, the morning show really got me ready for daily show, because the morning show, the radio show gave me the opportunity to be creatively different and think outside the box. It was the first place I worked where I was allowed to go, okay, I see how y'all do it, but is there a different way to tell this joke or to get to this emotion or this thing?

And God bless them, they let me try. You were really well known at the time for your prank phone calls. I have to ask if you're comfortable sharing. Were any of them staged? Negative. Not a single prank call was staged. I'll sue anybody that insinuates that on a play. Like in a way, it's a funny compliment for people to say they're staged.

But this was the Wild West, man. This is 0-1-2. You just call a strain. Because people still answered unknown numbers back then. I wasn't sure. All I know is there's, I just know that there were certain radio stations that employ people to do that. And I'm not, I just was wondering, but that makes sense. Oh, no, I get what you're saying.

But no, like most of the pranks I did also, I was put up to it by relatives. You know, they wanted you to prank call the people or whatever. Yeah, I know there's some radio shows that embellish the content for the sake of having something entertaining to show the people. But no, I never, never in a million years did I do that with my stuff? I was reading research on you. We're about the same age. And growing up in Birmingham, you were watching the same childhood show I was watching when I was in, at the time I was in Arlington Heights, Illinois, which was you can't do that on television with the green slime. My introduction to sketch comedy, I mean, really before SNL.

And I love that show. What do you remember from watching that show? I just remember the slime and the silliness. If we're talking introduction in the sketch, I remember he-haw. Oh, yes. That was syndicated. I remember seeing that on the weekend. Then I do.

You can't do that. Like, you can't do that. I just remember them being slimed, and there would be dialogue, and then there would be a funny sketch and stuff like that. But I remember just, I don't know, why I remember he-haul, and then I remember that donkey, this animated donkey being the transition shot from sketch to sketch. it's such a silly ass

such a silly thing but yeah I remember that I remember Danger Mouse if we really want to get it to Nickelode Penfold his sidekick was penfold I remember Danger Mouse

Yeah I need to watch an episode I have to say early Nickelodeon they have so much now but there weren't a lot of options back then for kids but yeah Nickelodeon was fun yeah especially for cable

I mean, most cartoons, it was all, you know, He-Man, Voltron, Transformers, G.I. Joe, of course. Like, I don't even think Disney, as a matter of fact, I know Disney afternoon wasn't even a thing yet. No, oh, not even close. I was going to ask, at the correspondence dinner, what was that pressure like? Was it just a regular gig, or did you feel a little bit more pressure than you would normally feel when you were hosting the White House correspondent's dinner? It's probably the most pressure I felt professionally as the correspondence dinner. just the weight of it you knew you were going to be watching this and it was going to get in the press yeah yeah also it's jokes that are literally of the moment these are jokes that will not be funny

tomorrow it might not even exist it the day before plus it's a tough room sometimes depending yeah i'd still say the apollo is tougher yeah there's no sandman at the at the correspondent standard The Apollo is tougher but more rewarding because when you get love from black people, man, there's just nothing like it because I am allowing you to heal me with your words. It's a level of intimacy, laughter. You're allowing someone to touch parts of you that you keep sheltered off because to laugh, you have to unarm. You have to be disarmed. It's a huge, huge compliment. Correspondence gender is a little different, though,

because I feel like half the room wants to hate you, and every joke, half the room will hate you. The catch is, you don't know which half of the room. And that changes from joke to joke. And so that part of it becomes like just grossly maddening to figure out how to isolate and how to stack the room. and figure out, you know, okay, if I do this joke this way, but if I put this joke after this joke, then will that joke be, like, it's just, it's a lot of that.

Are you still auditioning? Because, I mean, you were great in Fletch, by the way, and you did three years on the TBS sitcom. Are you still auditioning these days, or are you just focused on your show? No, I still auditioned. I get roles here and there. I was just in a film, Love Brooklyn, beautiful romantic comedy with Andre Colin, Nicole Bihari, and the Wanda Wise, and top of next year at some point, I don't

know when, they haven't set a release date, but I'll be in a Keanu Reeves, Jonah Hill comedy for Apple Plus, which I also audition for. But it's still fun to pop in and do other things. I don't ever want to be pigeonholed and just being a host. Smart, man. I don't want that. I would rather do other things. Do you miss stand-up these days? a little a little you know i had a i had a hulu special at the top of this year uh which will probably be the last stander special i do at least for a year or two you know

i have a book that just came out and my plan is to take that book and really use that book as a springboard for something one man or something different but you know i would love to write like a little more man show like i would love to go on a mike berbiglia ali sadique journey if you will oh i'm sure you've had so many of those i would love yeah that would be amazing you know like like i think like one of those situations would be fun but i don't i don't know man like i just think comedy everything's going to always come back to that yeah you never lose that that that love for performance but the type of performance, I think that's the part that is, I'm in a different state. I'm in a flux right now. I'm going to flux. I have to say, have I got news for you? So many people love

it. I mean, it's definitely, it was made for you, I feel. Like, it's such a great vehicle. And I wish you the best. And thank you so much for talking with us. This was fun. I hope you had an okay time. I'm grateful. Oh, yeah, good times. I appreciate you. thank you sir thanks for listening please subscribe so you never miss an episode on apple podcast please rate it and leave a review be sure to go to late-nighter dot com for all your late-night TV news and you can find my podcast at late-nighter dot com forward slash podcasts have a wonderful week and i'll see you next tuesday