Mike Birbiglia's Working It Out - 122. Roy Wood Jr: Perfect Jokes From an Imperfect Messenger

Episode Date: February 12, 2024

Roy Wood Jr makes a triumphant return to the podcast and he and Mike pick up right where they left off. The two old friends discuss the evolution of unconnected jokes into a more cohesive whole hour of stand-up. They discuss why Mike, Neal Brennan, and Chris Rock are all pressuring Roy to go even deeper with his new material about his dad. Mike and Roy break down the best bits from Roy’s new special Imperfect Messenger, and Roy shares two all-timer stories in the slow round. Plus, Roy gets candid on exactly why he may or may not be hosting The Daily Show.Please consider donating to I See Me, Inc.

Bro, I have the address of the descendants of the white people that own my family. I could zillow their house. So I got to go down there and fucking just see. Give them a bill? Yeah. Document it. Yeah, that's funny. Request back pay.

Hey, you want to go get dinner? You're going to get the check. Yeah. Hey, you want to go get dinner? You're going to get the check. That is the voice of Roy Wood Jr., one of the greats. Roy Wood Jr. is, I believe, unparalleled in the world of stand-up comedy. I just think all his specials are great.

I think he's a phenomenally interesting person, a fantastically interesting life story, a great talker, a great joke writer. Have I oversold Roy Wood Jr.? I just think he's great. I've known him a long time. It's his second time on the podcast. He is, if you're able to see him on tour, he is one of the great, the great comedians to see live.

Just the best. One of the very best. I know because I've followed him before and he's very hard to follow. So the point is, see him. And come and see me. I have a whole bunch of dates coming up. I just added a third show at the Chicago Theater, a second show in Atlanta. Significantly, I have an announcement about my Florida shows because we're rescheduling the Florida shows. I rarely, rarely do this. There are things that are beyond my control right now that are personal things. So I had to move those shows, but not for long. I'm going to move them. If you got a ticket for those shows, you'll get a notification.

It'll be on burpigs.com. Again, I hate doing this. It drives me nuts. But rest assured, I'm not moving these dates to be in Fast and Furious 11, which someone's going to be in uh fast and furious 11 which is which someone's gonna be in but not me but but that's not why we're moving these we're moving these for just some personal things um all the tickets will be honored uh but this could not be helped um the tour continues next month i will be all over colorado when i say all over i mean i, I'll be in Aspen, Colorado, Beaver Creek,

Fort Collins is sold out, two shows in Denver sold out, but we added a third show in Denver, third and final show in Denver. I'll be in Tulsa, Oklahoma for the first time ever. I'll be all over Texas, Dallas, Houston, San Antonio, three shows in Austin at the Paramount, which I love and where we premiered Don't Think Twice, the movie, many years ago. We just added a show, a third and final show at the Chicago Theatre. Gorgeous, gorgeous, marvelous theatre, one of the great theatres of the earth.

I added a second show in Troy, New York. I'll be in Rochester. We added a third show in Toronto. We added a second show in Charlotte, North Carolina. I'm going to be in Rochester. We added a third show in Toronto. We added a second show in Charlotte, North Carolina. I'm going to be in Richmond. We added a third show in Washington, D.C. We have a show in Niagara Falls. I had a bunch

of people say, how come Buffalo's not on the thing? I'm going to be in Niagara Falls. It's very nearby. It's very close. Niagara Falls. And then this summer, in July, I'll be in Sag Harbor at the Bay Street Theater. The Bay Street Theater is a gorgeous, gorgeous, gorgeous little theater. I want to say it's like 280 seats. I'm doing four shows there. One of them is an afternoon show, Sunday afternoon,

2 p.m. I think that's going to be fun. I'm announcing a whole bunch of cities for the fall coming very soon. Follow me at Burbiggs on Instagram or join the mailing list on Burbiggs.com to be the first to know. Today on the podcast, I just have such a great talk with Roy Wood Jr. We get into it. We talk about The Daily Show. I should know we recorded this episode before they announced that they're bringing Jon Stewart back to the show. So we didn't talk about that. But we talked about The Daily Show. We talked about Roy's dad, who's a fascinating and complicated person.

The key thing that we talk about today, I think, is how comedians take a bunch of seemingly random and unrelated jokes and turn them into something that ties together as a theme and what that process is like. And obviously, we talk a lot on this show about that topic, but we really get into the nitty gritty of it today here with Roy. He's a person I just love talking about process with. Plus, he tells a couple of absolute all-timer stories, some of the best stories you'll ever hear on Working It Out. I think you're going to love it. Enjoy my chat with the great Roy Wood Jr. Your special is so good

that it makes me reevaluate other specials I've watched recently. Thank you, sir. My wife Jenny and I were just watching it. We're just like, oh, no, no, no. Because we watch all the specials. We're like, no, no, this is a cut above. I'm just happy Comedy Central finally put it out for free on YouTube where people could actually see it.

Yeah, but thank you, man. Thank you, man. No, that means the special's unbelievable. It was fun to put together. It's fun to kind of tightrope walk. And then there is the sunrise the day after the special. Yeah. Where it's like, fuck.

Yeah, I got to write another hour. I'm living in that right now. I'm on tour to write another hour. I'm living in that right now. I'm on tour with my new hour. I'm like, oh yeah, you got to have a keep up to the old hour. I have the working shards of something,

but it's not necessarily all the material that I'm in love with. Like if you paid money to come see me, you will get a different hour from anything that is currently available digitally. Yeah Like if you paid money to come see me, you will get a different hour from anything that is currently available digitally.

Yeah. So you will get new material. Now, is that what I want to really be digging into? That's exactly what my tour is right now. It's just the funniest things I can think of. And that's what I have. Yeah. And then as things progress, I'm going,

oh, that joke isn't about that. That joke is about, like there's a bit that I've started working slowly. I got invited to, I don't want to say a sex party. I like the intro. Because it's seven days. So a party is one day. Okay. In my opinion. Like party is one day. Okay. In my opinion.

Like a retreat, like a sex retreat. But not cult, but it is groups of couples fucking all day. So you're with your partner at this? That's how it's proposed to me. I'm not dating nobody,

which is part of the bit. Okay. It's not a date. Like, this is a long-term relationship activity. Okay. So you got invited to this. To go to a suck and fuck on an island somewhere where other couples are sucking and fucking. And together you're all in a house.

Not sucking and fucking each other. Just, hey, we're going to talk about intimacy. And there's deeper themes to why the people are being brought together. Right. At its inception, that bit was just a run of sex jokes. Right. Sexual insecurities and performing, maintaining an erection in a group setting. Just easy, in my opinion, easier shit to mine.

Right, yeah. But then when you really start gnawing on the bone and getting down to the bone marrow, it's about how difficult it is to make new friends as adults. Yes, 100%. And so that's the bigger thing that I need to unpack. I've always loved your comedy, and I think part of it is the exact thing you're describing right now, which is you're not just

telling jokes, you're figuring out what's the joke under the joke. What is this about? You know, in your special Imperfect Messenger you do a really funny bit early on about facial, like an app that shows what you look like when you're 80 years old. Why would you need

an app like that? That's super funny. And at the end, spoiler alert, if people want to press pause on this, watch Imperfect Messenger, which is on YouTube for free right now and come back to this. At the end, you talk about how there's photos from the civil rights movement where we,

some of them are still alive. Yeah, white people at lynchings. Yeah. I need to know what they look like now so we can go have a conversation. Yeah, yeah, so we can go have a conversation. If only there was an app. Oh, if only there was an app.

And I got to say, man, I got really, I was laughing and I was really emotional at the end of your special. And I so appreciate it thank you man and you also tie back this thing with your son

where you're facetiming I think that's your son yes facetiming at the beginning and the end and that too I don't want to give it away people should watch it themselves

it was very emotional it's the simplicity of how easy it is to achieve happiness. And the older you get, the more difficult it is to have a sliver of happiness. And that's what the moment, that's what the bookend is supposed to be. There's days where my son is perfectly happy for hours with a cardboard box. A cardboard box. Yeah, you're FaceTiming with him at the beginning of the special,

and he's in a cardboard box. And this is something people always say about kids. It's one of the wisest things you can say about having kids. They're as happy with the toy in the box as they are with just the box. Yeah. They're good with the box. Yep. They're more imaginative than we are.

Yeah. As to what could make you happy. He's in a space shuttle, and then I close him up in the box, then I pick up the box and shake it to simulate liftoff when he was lighter. I don't have the rotator cuff for that shit now. But, yeah, like that interests me. You know, we talked a little bit about just unpacking this shit with my pops. But that's its own beast.

I've even tried to tell stories about my dad within the existing hour that I'm touring. And it's just too... It's spaghetti and chocolate cake. They are both delicious. but you cannot put them on the same plate when you say which two things the thing with your dad and what else the emotions with my father and then just like any other topics that i'm doing now that's just world analysis oh we're all alone in the world and how do you make friends and isn't making friends weird and then how do you break up a friendship when you're older and like that type of stuff and then also yeah i

remember the last conversation i had with my dad you know like i talked about like we talked about this i think off camera once just about when i did Finding Your Roots, and I found out all this extra shit about my dad that I just didn't know that reconstituted why he may have made certain decisions he made in parenting that I didn't agree with. So it forces you to see somebody in a different light. Can you name an example of that? Yeah. My father lost his father when he was four. Yeah. And then, and this is according to census data, there was no other male head of household

ever recorded in any home that he lived. So there was never a man in the house. There might have been men. He might have had men in his life, but there's not a man in the house. There might have been men. He might have had men in his life, but if there's not a man in the house on a regular basis, that's drastically different. That's a drastically different upbringing. So there's just a lot of things that I learned about him from that show

that to me painted a picture of understanding why he may have had a distrust not only of relationships, but of just loving people or having any type of long-term investments in people because people go away. Yeah. So why even bother with that? Like, that's just a weird emotion to deal with. So it's easier to be at a distance. Yeah, but I'm also the ninth of 11 kids by five women by one accountant. Some of the accounts I'm 11 of 13. So if you fucking like that,

it ain't for love. You're coping. What are you on? Like, what were you dealing with, bro? Right. Now what that is and what that was, I don't know. I got to go do all the digging. I got to talk to people, which is stressful because most of the people that can answer those questions are dead or dying. So that's the big fish to reel in. That's the fucking one-person show or maybe it's a book or something. I don't know.

But in the interim, figuring out how to make that funny is going to be a long, long fucking walk, bro. Yeah. So in the interim, I still write stuff that's still fun and observational. I still, I'm convinced, we talked about this last time you were on the podcast, I'm still convinced that you should do a solo show in New York instead of an off-Broadway theater for a while. Because I feel like your story is so layered.

It's so fascinating. You, Neil Brennan, and Chris Rock. Chris Rock wasn't as polite. Chris Rock is never polite. Motherfucker, what you doing? Do some other shit. He is not. Do that daddy shit. He is not.

You're not daddy shit. He doesn't beat around the bush. No, I love that about him, obviously. So I'm mining it, but you've got to go and mine it and then sit and chisel every rock and figure out what is the show. So I go get that. Bro, I have the address of the descendants of the white people that own my family. Unbelievable. I could zillow their house.

I mean, come on. So I got to go down there and fucking just see. Give them a bill? Yeah. Document it. Yeah, that's funny. Request back pay. Hey, you want to go get dinner?

You're going to get the check. I thought about if I was rich enough, I thought about just wherever they work, buying that company. Oh my God. Jesus Christ. So I could own them. Oh my God.

Like I've thought about that. Have you done that on stage? No. I mean, that's funny as hell. But does that connect to the dad shit or does that connect to the revenge and racism and the trauma and the generational and does that segue nicely with self-checkout jokes and the sucking fuck jokes yes yes and yes and yes and yes all right right we're gonna have this gonna have to be a long conversation. Because it all relates.

Because it's all from you. That's why. But even if we just go with the white people in Georgia, I feel like there's more to be mined if I actually go down there. The white people whose descendants owned your... And they're also not rich yeah which is a whole another analysis of slavery it's just how many white people fumbled the bag with slavery like you had people and they used to which is just how vicious corporations are. They took slavery from white people. Only they made profit.

How the fuck are you three and four families deep into owning people and you still couldn't turn generational wealth? These motherfuckers, they're not doing well, bro. They're in a small Georgia town. You can't slave shame people. Haven't you heard the new rules? You can't slave shame people haven't you heard the new rules you can't shame people that's massive shaming like the fact that i don't know it makes me laugh and then i'll have to figure out how to make it funny on stage and make white people feel okay with laughing at it. Please. But the idea that part of the only reason why Dr. Henry Louis Gates and everybody at PBS,

part of the reason why they were able to trace my family so far back was because my family was owned by a series of poor white people who could only afford a couple of slaves at a time. who could only afford a couple of slaves at a time. Like, a lot of enslavement was not the big industrial plantation. Right. A lot of it was just two or three black people working for a small family. Yeah. So there's something in there. Yeah. But I got to do that bit from a place where I'm still respecting the institution of enslavement.

Yeah. But also going, ha-ha, you broke motherfucker. You could only afford three niggas. You ain't shit. Jesus Christ. And it's interesting because when you start introducing thoughts like that, a lot of white people get very tight. Like, white people are very scared.

They're very conscious of trying to do the right thing, including not laughing at the wrong thing in a live comedy show. Troy, I'm going to do you one better. You're talking to one. One of the good ones. Like, there's this wall of empathy with audiences, with mainstream, with white people, that I feel like I have to work through.

I learned that working with Mulaney. When Mulaney came back out on tour, I opened for him a couple times. And granted, his crowd is already charged up to give him a hug. So they want to hug anyone. They're kind. That's so funny funny i'm not saying that it's insult but it's just a do you want to may i hug you this i just appreciate you and so like on steroids of empathy steroids of empathy yeah and i've never performed for an audience like that before ever. I've never performed for an audience that was so as ready to show concern as they were to show laughter. Yes.

Yeah, I have that too. I have certain jokes sometimes where I go like, oh, that's too much for my audience. Yeah. My own audience. Okay. And so I'm learning that now with my audience. Okay, and so I'm learning that now with my audience when I go my dad is buried next to another woman and we didn't find

out that he bought his and hers burial plots until we were walking the casket up the hill to the graveyard. But also, one of the most illustrious and decorated civil rights journalists this country has ever seen. So deal with that the way I did. Right.

Like, in other words, he had a mistress. Correct. And also, he was a very honorable person in 10 different ways. Completely honorable and $15 billion. When I did the correspondence dinner, after the correspondence dinner, I was getting handshakes from journalists whose first job was working with my father. Wow. There were so many people in that room where working with my father was their first job.

So many people, especially black journalists. So he's- He's a civil rights journalist in Alabama, right? All over. All over, okay. Well, at the time in Chicago, St. Louis as well, but he would embed himself in Vietnam, South Africa, Zimbabwe, wherever there was war.

So when you were the White House Correspondents and people came up to you, journalists, and said they sort of looked up to your dad. Your father, brr, story. Wow. Your father did this, brr, story. So you can have empathy, but this is a comedy show, my nigga. I need you to laugh.

Yeah. But I can't take that away from you. And most people don't want to give it up. Most people want to feel sorry because they want you to know that you care. And with Mulaney's audience, it was the first time I became self-aware of like, okay, if I'm going to start talking about some

stuff where I need you to laugh with me because I've already dealt with it, how do you bomb squad, red wire, blue wire, the empathy wire without cutting the humor wire in an audience member's psyche? And what are the jokes that can help clip that wire first? And then I can get into the deep shit and it be funny.

Yeah. And it'd be okay for you to laugh because I don't deal well with an audience that puts empathy first. And so that's why opening for Mulaney those couple of times, that was an important week. Yeah. Because it was like, oh, okay. So if you're going to try and get into some shit,

oh, oh, okay. So if you're going to try and get into some shit, then you've got to make sure that this is worded and this connects to this and that. And now you're talking about acknowledging the thoughts and the feelings, which was a digression I never thought of because I've never had to fucking do that. Of course. Honestly, it's pretty new in comedy.

Also. It's pretty like in the last five years kind of energy. I would describe it. This is all George Floyd. I want to care and concern. I'm cognizant of what is happening. So I want to be sensitive. I want to be an ally, which you talk about in your special.

Not just race, but just across all levels of I care about your plight, whatever your plight is thing. So, okay. levels of I care about your plight, whatever your plight is thing. So, okay. Because the thing that I had up until that that protected me was black laughs. Black laughs. If I'm doing the edgy joke about race and black people laugh. Yeah.

You have black audience members that are the tent poles of the audience. That's the cue for you to, that's the blue wire clip. It is. I don't even have to clip the blue wire because you saw the black person laugh, so now you know where I'm coming from. Absolutely. Yeah, I know what you mean, but I actually think you're so good at reasoning through ideas on stage that you can reason through the audience's experience of what you're saying in a way that doesn't feel hacky. Yeah, I'll figure it out. I feel good about where I am. I mean, there's probably still another 30 minutes of just new thoughts that I haven't mined yet.

I don't know. I just go to different parts of town to test different shit. Same way. I'm the same. Did we talk about that last time I was on the pod? It's been the same. Did we talk about that last time I was on the pod? About how I like, when I'm working an hour special,

the week before I tape, I go to Peoria, and then I go to Atlanta. Oh, that's smart. Yeah. Well, I try to do it the other way around. I try to put it in front of as many black people as possible, and then put it in front of as many white people as possible. Yeah. And then tape. Yeah.

Once the jokes are dialed in and chiseled down, all right right black people have i nailed everything is there any any holes in this these theories before i take this out to the mainstream and then and then you go to peoria to see how well they can take a punch to the mouth well that's you have that joke in imperfect messenger that i love which is basically like sometimes there's too many american flags oh yeah how many american flags equals a confederate flag i'm just like i've had thoughts like that my notebook you nailed it you nailed that joke the one joke that took me a minute to kind of work out was the Black Brits,

that Black British actors who play African Americans in movies about African Americans. And like, that's one that like within the black community, that is a serious, serious issue. And it's touchy. And it's like, okay, you're an actor. And if you can do a regular accent, cool. But also, should that role go to an African American who doesn't have to do an accent? So it's the debate of heritage versus talent. And I did that joke early on, and I got checked by African American. And the basic network note I got from this person was it was coming across too much like I was protecting and defending black British actors.

Oh. And saying that they have a right. Yeah. And that's not what I was saying at all in the joke. Yeah. The whole point of the joke was you don't know they're British. Right.

And then you find out they're British and there's a feeling of betrayal. Yeah. Because you don't know they're British until they do the interviews for the movie. Yeah. So the whole joke is just about discovering that. And it's a long, in hindsight,

I probably could have trimmed some fat out of it, but it was just a long walk to talking about how, when I found out the day, every black person has the day they found out Idris Elba wasn't from Baltimore. Oh my God, that's so funny. And that's the joke. It's so funny.

And then from there, we're right into Leo DiCaprio. Yeah, yeah. And we're right into- Being in Django. Yeah, white people, the most, the bravest actor is white people who say nigga in civil rights movies. And that joke was much wider. Yeah, that joke is amazing. But it only worked in black audiences if I gave props to Leo.

Because Leo is seen as above the fray of regular white actors. Wait, with black audiences? With black audiences, only the Leo part got the laugh, so that's why the rest of it got trimmed. Mainstream audiences would laugh. There was a lot of fat. The joke in the longer version, in the longer original iteration, was that it was other accounts of white people saying nigga

in movies with black people in the room yeah and the idea that man that's great white actors man but it was um benedict cumberbatch yeah in 12 years a slave i was like yeah man also you remember 12 years a slave you don't fucking black people couldn't pick benedict cumberbatch out of he's a great actor i said i remember 12 years a slave you don't black people couldn't pick benedict cumberbatch out of he's a great actor i said i saw 12 years a slave in the theater respect first of all thank you for your allyship thank you very much applause i'm gonna leave some room for applause um paul dano's character is a racist and he gets like I think he gets

knocked down or punched or whatever the audience cheered yes like they were at a football game

yes that's what made Django great it was wild it's a hero it's amazing like that

that whole run it felt too much like man I like it when white people call black people niggas. And that's not what I was trying to say. Oh, interesting. But if it's taken like that, you have to respect the response. Like, I'm not here to go to battle with the audience.

If just mentioning Leo DiCaprio and Django gets the laugh, then I've made my point. Trim the fat. There's no need for me to have you annoyed with me by the time I get to Leo. We could just do Leo and just say Leo was the best of all of them because he did it in front of Samuel L. Jackson.

That was a bit that needed a lot of refinement over the course of a year in front of... This is one of the things that I struggle to explain to people who aren't in the comedy field about stand-up comedy,

is sometimes people will see somebody live and they'll go, I don't like how he said this or she said this. And you go like, that's the nature of the live experience of comedy is actually Roy or me or whoever it is. We're actually going too far on purpose to know that that's too far. Yeah. And then, and if you're a comedy fan, in my opinion, you're signing up for that as a concept.

Yeah, this is a workshop. I loved that people were so upset when you said that you weren't going to take over The Daily Show. You were trending for a few days. I don't know why people were mad. We were upset because you seem like such a logical host for the show. I don't think that... Well, first off, I'm appreciative of all of that. If anything, it just showed me like,

oh, okay, well, people were watching. Yeah, yeah. Thank God. People were watching. People appreciated what you were doing on the show. If anything, that week of everything, when it came out that I was leaving the show, it just gave me some validation.

Like, okay, well, there's space in this world for more of my ideas, so let me just figure out how to do them. And that's when you decided to plant the story about Haas in the New Yorker. That's literally why everything kind of fell apart. Is it? Well, as far as it was told to me, Hassan was the guy. It was going to be Hassan. I heard that, too.

Okay, okay, cool. So I'll hang out here the rest of the year, and we'll see what Hassan wants to do and what his vision is and whether I fit in that. I'm still trying to sell my own sitcoms. I'm trying to write movies. There's other shit I want to do, but let's see what... It's, as Ronnie Chang puts it, and I quote, the best job in comedy.

Yeah. The Daily Show is the best job in comedy. I would argue number two is Saturday Night Live. Yeah, the weekend update job. Any job at 30 Rock. Any job on that floor, to me. It's hard to say which one is the better job in comedy, but when I say best job in comedy, I'm talking about what you learn while you're there,

the people that have graduated from those places, and the level of longevity that you could have within that building if you just do the job. More plays into SNL while people who come and go. If you talk to anybody who's ever worked for Lorne Michaels, when I was there, man, it was great and doing this, this, and that. You just learn a lot. So I wasn't going to just leave Daily Show just because there's a new host.

But then the question becomes, what does that host want? Then the New Yorker article comes out yeah so new york article comes out and then the buzz is that there's a shift at comedy central and whether or not hassan's still going to be the guy which eventually turned into he's not going to be the guy right this is so people know this is when Haas and there was a New Yorker article that I think was a bit of a hit piece about the veracity of some of his bits in his specials. As I said to him and to another person, they flipped over his standup comedy and looked at the nutrition facts. That's so funny. And try to decide whether or not it had the right percentage of this or that. Yeah. Okay.

So it comes out that he's not going to be the guy. So the question was just, you know, well, what's going to be the process now? Yeah. Like, I'm sure you've got to figure out who's on your list. Yeah. who's on your list. Yeah. And they couldn't, in my opinion,

they couldn't articulate adequately enough for me what that process would be. Yeah. And whether or not I fit into that process. I respect that it's a process. It's a tough... Yeah. As we're recording this, they still have not chosen. Yeah.

At the top of January, they still have not... We're talking about top of January, they still have not. We're talking about top of October. That's three months ago. So what I feared in October was being in a position in January where maybe you do choose a new host. Yeah. And it's someone that does not want me there or someone I don't want to be there with or it's a format that I don't want to rock with. And I feel like after eight years, I've earned the right to step away for a minute and just,

well, let me just see what else is out there for me. And if they decide, hey, you want to host? Hey, the door's open. Okay. Well, you got my number. But to figure out what's next for me while also being a correspondent, is insane that is an insane endeavor to walk to walk into while also trying to be a father yeah you cannot do all of those things adequately one of them will suffer yeah so love you guys sorry about the house and shit but i'm gonna take i'm gonna i'm gonna step away yeah i think the reason why you would be such a good host for that show is that the way you speak in Imperfect Messenger is they're hard jokes, they're edgy jokes, but somehow we feel like we're friends with you. I appreciate it, man. You know, it's not an easy job. It's definitely, I think hosting any late night show, like if you're offered an opportunity, though, I have to say yes.

I can't say no. I'm going to stop short. It's not some militaristic obligation or a calling, but if somebody is going to give me 30 minutes on their channel every night. Yeah. Yeah. I want to figure out what to do with that and how to build opinions and perspectives. Though the more I look in research,

the more I feel like now you might be able to just do it alone. Yeah. If you're smart enough about it, because you have to go and, they're not rolling the dice on a lot of people. So I don't know, man. I don't know what they're going to do. I just think, I just hope that The Daily Show

continues on with the host, especially at least for election, for the election year. Yeah. Yeah, no, I agree. All right, this is called The Slow Round. Can you think of a time when you were so scared you ran away? I mean, I've had guns put on me before. A couple times.

Usually cops, which is oddly scarier. Oh, yeah. Only because in the streets, there's still rules. Oh, interesting. If you asked me to choose between two people pulling a gun on me, I would rather a non-police officer be the person holding the gun. Wow. Just because that person might not get away with it and they know it.

So maybe they will hesitate. Now, it's important to also say every police officer that's pulled a gun on me didn't shoot me. So let's be fair. But there was— A pimp maybe stole your class ring? Oh, yeah, when a pimp stole my class ring, yeah. There was a dude—it's a long story, but this girl stole my class ring. We had a, this was in college, we had a stripper over to the house,

and she was going through shit upstairs when she was supposed to be in the bathroom changing. God. It was for a friend's party, and we had the biggest apartment of our circle of friends at the time. So it would be fun. You're the stripper. Long story short, for a friend's birthday, we hire a dancer. She dances. She needs a ride back to her neighborhood.

I'm the only person at the time at the house with a car. I give her a ride back. I worked at Golden Corral at the time. At Golden Corral, you couldn't wear jewelry on the clock because it'll fall on the mashed potatoes. So, my class ring was in a cup.

It was in a cup holder. I know it was in a cup holder because that's always where it is. I drop her off. I come back home and I'm getting ready for bed and I look around my room. I'm missing a watch. I'm getting ready for bed. I look around my room. I'm missing a watch. I look at my watch drawer.

There's two watches gone. I go, where the fuck is my ring? Oh, it's got to be in the car. I go back to the car. The class ring is gone. I go back in the house. Where's your shit? Everybody check your shit.

Motherfucker got us. Motherfucker, she got us. Oh, my God. Everybody's in the room checking their shit. Just all types of shit is missing. Where'd you drop off? We got to go back and motherfucking find her. I'm going, you're goddamn right.

We're like 18, bro. We're 18. Oh, my God. We got to find her. And like some grown woman ass stripper, like fucking 34, has just gone through our home. And just fucking, It just got us. Wow.

Well played. I'm not even mad about the shit. We was just dumb. Yeah. That's crazy. So we go back to the street where I drop her off, and now we're out just fucking walking. Walking in the middle of the street like fucking Grand Theft Auto.

Just fucking in the middle of Tallahassee. Fucking French town. So we're doing laps Tallahassee, fucking French town. So we're doing laps up and down every street in French town. And we see a dude. He was the dude that facility, he was the middleman of the transaction. And so, motherfucker, where she at? Motherfucker, motherfucker,ucker bitch took my class right. Like, now that I'm older, I'll say that.

And we're like banging on this hood of his car and shit. Like, we're like, we've encircled this man who we've entrusted with hiring a trustworthy dancer for our evenings. And we believe she's taken some of our belongings. Yeah. And so we're fucking banging on the fucking hood. And this motherfucker just takes a long drag of his cigarette. He rolls the window down.

He just goes, look here. Look here. I don't know what y'all came here for, but I'm going to circle the block. And if y'all came here for, but I'm going to circle the block. And if y'all still here, you're going to get what you came here for. Oh, gosh. And I didn't even know what the fuck that meant. Yeah, yeah, yeah, yeah.

But it felt like we should leave. Yeah, we got to leave. We should leave. Yeah, yeah, that would be my cue. Never pulled a gun, never said anything else, rolled his bundle up, and cruised slowly up the block. Gave us ample time, and we just fucking left. We fucking left. Like, and in hindsight, I cannot think of a single person

who still has their high school class ring. That's so funny. You got to put that in the show. Yeah. You got to put that. Well, that goes in the show for sure. You know how stupid you got to be to die over a fucking ring that says you're a Sagittarius and you like baseball?

Fucking Herf Jones. That shit is the biggest. The class ring is one of the biggest fucking scams. What is a song that makes you cry a prototype outcast Andre 3000 it's an outcast song called prototype yeah I hope that you're the one

if not you're the prototype tiptoe to the sun and do things I know you like yeah that's the one that's the one that would get you thinking about women you should have treated better it's like hi fuck i fucked that one up too that's powerful and then i play bombs over baghdad to offset it

i'm doing 3000 man he you read that story recently right bare naked soul bro he bears his soul in his lyrics you know he left left left music and now he does like some other type of music

yeah he plays flute now he's released an album a whole album and then it's been revealed he's been ghost fluting on popular hip hop tracks ghost fluting for the last 20 years

ghost flowers which by the way of course right he's such a genius ghost fluting on popular hip-hop tracks for the last 20 years. Ghost flowers. Which, by the way, of course. Right? He's such a genius. He learned the flute and became so good at it that he's just on flute tracks? Yeah. Yeah.

I've thought about learning the piano just to become a piano comic. Oh, yeah. I don't even know what jokes I'm thinking. But I've legit thought about that. Like, fuck, man, that'd be nice.

What's the most absurd thing you've ever done while drunk? I got drunk with a woman in Negaunee, Michigan after a show. Just, we're pretty buzzed. We're like four or five then.

We went to her house and we start making out like in the, like as soon as we get in the door, door slam, boom, making out.

Real chemistry. And then you hear upstairs, Mommy, Mommy, you were gone a really long time. Oh, my God, Roy. I'm like, oh, fuck. Roy.

We're in some child neglect shit here. And you now like, you're drunk. Oh, no. Oh, no. I hate this story, Roy. Oh, no. I hate this story, Roy. Oh, my God. She's like talking to the kid between kisses. I'll be right up.

I'm going to check on you. I said I'd come home and check on you. I'm home, right? And I'm like, oh, fuck. Wow. You're really living wrong, man. And like when you're drunk, you get like, I believe anytime you're drunk, I believe this, and granted, I've only done alcohol and shrooms. But I believe most times when you're drunk, you get these 30-second sobriety windows.

Like the eye of the storm passes over your brain. And mine hit right in that moment. And I go, she goes, you want to fuck? I'm like, yeah. Go check on your kid and we're going to fuck. Oh, my God. I left my condoms in the car. I'll be right back.

And she said, okay, go get the condoms. And I fucking ran. I fucking ran. You want to talk about running from some shit I was scared of? Fucking that. Ran to Ghani, Michigan. It was five degrees. And I fucking took off up the street to call a, this is pre-Uber.

So I'm just, I'm just a black guy in the upper peninsula of Michigan. We're like four hours, three hours north of Green Bay. Closer, literally closer to Canada than the rest of America. And I'm a black guy in a fucking nice neighborhood at one in the morning, drunk, running up the street away from a woman who has left her child at home while she bar hops with a comedian. And that's got to be in the show. Nah. My mom's got to, no, because my mom's friends will watch it. They're not going to watch this podcast.

My mom's friends won't watch this. I get it. But they'll see the show. This is the good stuff. What lesson is there in that other than start back dating black women? What lesson?

Because no black woman would have left her kid at home. I think you could tie it into the loneliness stuff you were talking about earlier. It's the last time I strayed from my race. That's a lot. But I still think you can get it in on the show. I also think you could build it, you could go into it by saying,

I'm uncomfortable talking about this. You know the problem with me and sex material, too? Yeah? I don't think the audience buys it. They don't buy that I be fucking. I think that that's an issue whenever you talk about sex is that like i've never breached it ever when in my persona what if anything about me even says like i know the persona is that i'd excuse me madam would you partake in intercourse

perhaps maybe after we get to the you can talk about sex if you're not getting any. Right. If you're in a drought, you can joke about being in a drought. But like I've never, 26 years of this shit, I probably have three sex jokes total that I've ever even attempted. And the only one that worked was a dick pic joke. And I didn't like that one because it just was too self-deprecating. It didn't fit in anything. It was self-deprecating. And I just didn't.

So I just generally don't do sex material. So we tell them a story about a horny, neglectful mother. Yeah. Like, I don't know how to get into that or where to put, like, it might have to just be a whole sex show. Yeah, could be, could be. Well, you have the sex party at the front that we were talking about.

But then also, I just think it's worth talking about that it's an uncomfortable topic. And that people will notice that. If you point out, if you hang a lantern on it, that is uncomfortable. It's a type of racism that is subtextual to culture, which you talk about in the Imperfect Messenger special. You can talk about sex as a black comic if you're hot. Yeah. Like. Who?

Bill Bellamy talks, but Bill Bellamy's romantic. Let me take that back. Yeah. Bill Bellamy is not just like, I be fucking these. Bill Bellamy is sensual. His comedy talks about, and I got the roses and I laid it out. Ladies, you know how y'all come in there with the lingerie and I be looking at the lingerie. You could believe Bill Bellamy be fucking and getting lingerie.

He's married now. Let's be respectful. But Eddie Murphy would just talk about casual sex right in his set and I don't think it was ever thought he's a big sex symbol yeah yeah you know one way or the other yeah Patrice O'Neill in a way there's something handsome about Patrice in the sense of the boldness in which he talked about sex and getting sex where you never question whether or not he's into some stuff. But also Patrice talking about sex was also on the extreme side. You know, he's anal and, you know,

you have to be finger-fucking a girl and then blah, blah, blah. It's just like, oh, okay, I'm with you on this journey. Right, right. Whereas I'm talking about self-checkout. Right. No, I get it. I get journey. Right, right. Whereas I'm talking about self-checkout. Right. No, I get it. I get it. You're talking about mundane topics.

Yeah, it's like— And then you're like— I mean, I'm talking about gun control. I'm talking about mass shootings. Yeah. And then I'm going to go to sex. I just think it's a very difficult—I have found it within my act to be a very difficult thing to merge into traffic. Matt, look, I get what you're saying.

I hear you. You're experiencing it with the audience, and I'm not there. But I'm telling you, when I watch you live and I'm in the audience, I feel like you could go anywhere. You're one of the few comics who I know who could go anywhere. You can go into politics. You can go into personal stuff. I know who could go anywhere. You can go into politics. You can go into personal stuff. You can go into sex stuff.

You can go into stuff about your dad. That's just what I think. All right. Thank you. That's just what I think. I've been doing a thing that's been working about how, like, I spend a lot of time with, like, dads. My friends, my daughter's friends, dads. And I just go, like, these dads. I go, don't tell them, but they're losers.

The subtext, of course, is I am as well. Yeah, exactly. And what's funny is it's one of those bits where the audience laughs just at their losers. And it's like not even a joke. So it's like one of those things where you know you you know, you're hitting a nerve, you know, there's something going on. So I just did a free ride on this. I go, dads are a troubled bunch. They're nervous. They've recently developed a stutter. They look like they just come back from a war. Most of them have not been to a war. They're afraid to speak or say anything that would contradict anyone else in the family.

And then I go, this is a mat and I haven't done this on stage yet but I go this is a massive shift in my lifetime when I was a kid my dad was like the owner of a restaurant that was my family he showed up when he wanted he disappeared for weeks he was much nicer to the customers than he was to the staff yeah yeah that's funny but if you have anything on that because i i'm just trying to it's like and the other thing i had is like my dad growing up was like the dad in succession without all the money is there maybe there's something to explore with with how you met all of these dads. Yeah. Like, for me, most of my interactions with fathers is within the parenting groups. Yeah, dropping off to ballet, dropping off to musical camp.

School, assembly thing, or whatever. School, yeah. Right. Or swim class, and you meet other dads outside of your dad's circle. Because it's like there's like two, maybe there's something. Three groups or whatever. Yeah. Because then it's like, well, what are the types the dads you'll be closest to or almost like brothers in a way you know then there's the dads that are like you know the sports and the extracurricular dads right like that's a that's a different subset right in other words breaking

apart the dads from a monolith of just being losers to like here's the different types of dads i interact with. Correct. And then deciding what is the losing thing about each of those dads. Yeah, yeah. You know, I don't know if this is true for you, but maybe it's something you can put in there. But I do think the thing I find interesting now, and maybe I'm just wrong, and maybe social media and texting has done this, but i'm way more in communication with the other parents just on some pta pta group texts it's endless there's way more communication

now than what i remember my mother having with other classmates moms oh yeah and it was literally just hey my son is coming over there did he say it was okay for him to come? Okay, all right, you can go over to Ms. Parham's house. Like it was that type of stuff. So maybe are the dads losers or are you just learning too much about them now? Oh, that's nice. Maybe we know too much. Yeah.

You know, but then also why are you a loser? Yeah, yeah, no, certainly. I think that's what it has to get to. but then also why are you a loser yeah yeah no certainly i think that's what it has to get to and it's like why it's like i gotta go deep on what is how does that joke turn on itself yeah my stuff god bless you because you have so much more fleshed out my stuff is just literally random run-on sentences. Like a lot of it starts with random thoughts. Yeah. And then I just don't know, you know, where to go with it.

Crack is the only drug I've never been offered casually. That's how I know it's good. That's funny. I've just, and that's serious. Like, I've never been offered, I've been offered every drug, but like crack is not a communal, as far as I can tell,

it's not a drug that people all get together. Hey man, we're doing crack out back. Yeah. No, you're not. Yeah. It's just for you. It seems like a solo drug. Then there's, America Really Be Broke. Is any other country's space program selling T-shirts?

That's good. I don't feel confident about NASA. They sell merch. Yeah, yeah. Merch is the sign of someone who really needs $20. That's very funny. But it's just such a... That could easily be a tweet if I wanted it to be.

I'm going to really continue to hold your feet to the fire about doing a solo show, and to Chris Rock's point about your dad. Because that stuff, I love. And I think that all this stuff, you know, you with the single mom

in the Midwest, et cetera, I think all that stuff ties in. That's just my thought. And I want to see it and I'm a fan and I want to be a part of it. God damn,

that girl was hot, too. I almost stayed, bro. The fact that you didn't stay actually kind of breaks my heart. I almost stayed. No, you can't. You can't have some seven-year-old seeing that. No, no, I know. But all right.

That kid would grow up and be a comic, and his first bit would be about seeing his mom fucking some black guy. If I fuck that woman, that kid's for sure a comedian. Let me cut you out there. The final thing we do on the show is cold-breaking effort, because is there a nonprofit that you like to contribute to? Mommy, you were gone a long time. Oh, my to? Mommy, you were gone a long time. Oh my God.

Mommy, you were gone a long time. I can't take it. I can't take it. You got to put that in the next hour. I'm telling you, you got to put that. Don't you think that it takes your friends in comedy to tell you which bits they have to do? Yeah. And that's me telling you, you have tell you which bits they have to do? Yeah.

And that's me telling you, you have to do that. You have to do that story. All right. Working out for a cause. What's a nonprofit you like? And we'll contribute to them and link to them in the show notes. icmeinc.org. icmeincorporated.org.

They're a wonderful nonprofit in Birmingham committed to cutting off the school-to-prison pipeline by promoting literacy amongst young people. Give us books involving authors and characters that look like the kids they're giving them to. So, talking black, brown communities, Asian communities, et cetera. The more kids, the quicker kids can read, the less likely they are to end up in prison. It's like statistics on it. And it's run by a woman that's a former elementary school teacher.

Left the classroom to start this shit. So I know she's dedicated and serious about it. They're a dope organization. I know a lot of the people involved. I've done stuff for them before when I'm back home in Birmingham. Well, we're going to contribute to them. And if people want to do the same,

it's icmeinc.org. We're going to link to them in the show notes as well. Roy, you're the best. I mean, there's very few people. You, Mulaney, Chris Rock. I mean, I don't know how many people I could say that to sitting in that chair where I go, I don't know if you're the best. I don't believe in that, but I think you're in a class of your own. Thank you, brother. Thank you, brother.

I appreciate you being here. I'll tell the Nagani, Michigan story soon enough. All right. Working it out, because it's not done. Working it out, because there's no hope. That's going to do it for another episode of Working It Out. You got to see Roy live on tour this week. He is in Iowa City, Minneapolis, and Madison.

He's at the Wilbur in Boston March 15th. Go to RoyWoodJR.com for his tour dates or follow him on Instagram at RoyWoodJr. That's RoyWoodJR. You can watch the full video of this interview on our YouTube channel, at Mike Birbiglia. You can subscribe. We're new in this YouTube game,

but man, it's just a whole new group of people finding these episodes, and when you watch them, it's interesting. You see the body language of it. You sort of, I don't know, maybe you feel more like you're in the room with us. It's fun.

The YouTube videos are fun. Graham Willoughby designed the cinematography for the YouTube videos. Just, I love it. It's been a really cool dimension of the podcast since June. Check out berbiglia.com to sign up for the mailing list to be the first to know about my upcoming tour dates. We're announcing a whole bunch of holidays soon. Our producers of Working It Out, and we work very hard on the show, are myself

along with Peter Salamone, Joseph Birbiglia, and Mabel Lewis. Associate producer Gary Simon. Sound mix by Ben Cruz. Supervising engineer Kate Balinski. Special thanks to Jack Antonoff and Bleachers for their music. Jack Antonoff on fire at the Grammys this week. Come on!

Come on! Jack Antonoff, producer of the year, again, again and again and again and again and again. I retweeted it, but he just, you know, gave a beautiful speech, and hopefully we're going to have him back on working it out in celebration of the new Bleachers album, which is coming out in March.

I'm not even, I don't know if I'm allowed to even say this, but I heard it and I love it. I heard a sneak preview of it that Jack slipped to me and I just love it. It's beautiful, just a beautiful, beautiful album. And it's so from the heart. And he's just an amazing, amazing musician. I appreciate him so much. Of course, his group, his super group, Redhurst, did the music in The Old Man and the Pool. That song

that plays at the beginning of The Old Man and the Pool and the end of The Old Man and the Pool is a group called Redhurst with Jack Antonoff, Soundwave, and Sam Du, who you might have seen, I think all three of them, appeared on stage at the Grammys with Taylor Swift when she won Album of the Year. I think they were all producers on that album. That's a super group if I've ever seen one. That album, that Redhurst album, is incredible. If you're looking for new music, that is an incredible album.

Special thanks, as always, to my wife, the poet J. Hope Stein. Her book, Little Astronaut, is beautiful. It is in local bookstores or online now. Special thanks, as always, to our daughter, Una, who built the original radio fort made of pillows. Thanks, most of all, to you who are listening. If you like the podcast, just tell people and write it on Apple Podcasts. Tell your friends, tell your enemies.

For example, maybe a pimp stole your class ring and you say, hey, why'd you do that? Why would you do that? Now you're my enemy. But let's put this behind us i'll introduce you to a podcast where comedians like roy wood jr come on oh you know roy wood jr oh you oh you know him oh because oh got it okay all right thanks everybody we're working it out we'll see you next time