Sunday Sitdown with Willie Geist - Nikki Glaser on New Standup Special, Roasting Tom Brady and How Comedy Helped her Survive

Episode Date: May 3, 2026

Nikki Glaser had long been refining her comedy chops before turning heads with The Roast of Tom Brady and as two-time host of the Golden Globes. On this week's episode, she sits down with Willie Geist to discuss the long grind to arriving at this moment in her career, her latest standup special “Nikki Glaser: Good Girl” on Hulu, and doing her raunchy standup in front of her parents who have supported her every step of the way.  She also talks about breaking in to acting starring alongside Kim Kardashian in the upcoming movie ‘The Fifth Wheel. ‘ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey guys, Willie Geist here with another episode of the Sunday Sit Down podcast. My thanks, as always, for clicking and listening along. I am so excited to bring you my conversation this week with, for my money, one of the funniest people working right now, Nikki Glazer. Of course, in the last couple of years, the world has come to know her as the hilarious host of the Golden Globes, working that star-studded room, and for that performance, now legendary. on the roast of Tom Brady on Netflix where for about nine minutes

she just eviscerated the greatest quarterback of all time. But it's been a long road to this starring moment for Nikki. She's been at this stand-up thing for 22 years. She first tried an open mic night while she was in college.

She was going through a lot in her life personally at that time. You'll hear her get into that. And she tried comedy kind of as a lark. And boy, she fell in love with it right away. Called her dad backstage and said, this is what I'm going to do with my life. But it's been a build.

Small stand-up clubs, comedy central roasts, all that getting her to where she is now. Time 100, she just landed, one of the 100 most influential people in the world. She, when we got together for this conversation, the night before, she had been there among all those stars as well, roasting them in the process on stage. But it's just one of those things where people look up and say,

wow, overnight success. She did the Gloves. She did the Tom Brady roast and look at her now. she's been building to this for a long time and it's well-deserved. So she and I got together at a place called the Olive Tree Cafe. Olive Tree Cafe is in New York's Greenwich Village, downtown, and it sits above the comedy cellar, which is what it appears. There's a staircase that goes down into the cellar of a building, and in this tight little room is where everybody who's anybody in comedy has started, who's waited in line to go on as a 20-something comic at 2 o'clock in the morning, or

Or if you're a big comic like Nikki Glazer, now you go in and hone your material there because you trust the audience and you trust the room. So after you do your set downstairs at the cellar, you come upstairs to the Olive Tree Cafe, you sit, you talk about your set, you meet with other comedians. There's one corner booth you'll hear Nikki says she's still intimidated to go sit at because that's where the big stars really all sit. So picture the two of us sitting, Olive Tree Cafe, right below our feet downstairs in the basement, is the famed comedy cellar. Also, something you should know, her wonderful, wonderful parents, Julie and E.J. are sitting just off camera. She brings her parents everywhere, and they were there and they couldn't have been nicer. We'll talk to them a little bit later. You'll hear that as well. I should point out that her parents were on the front row of her latest comedy special, which, my goodness, if you haven't seen it yet, please watch it. Nikki Glazer, good girl, on Hulu, and then imagine her parents, her sweet parents sitting on the front row of that performance. All right, I'll get out of the way now. You sit back, relax, and listen to Nikki Glazer right now on the Sunday Sit Down podcast. Hi, Nikki. Hi, Willie. Thanks for doing this. Thank you for doing this. I'm so happy to see you, especially at this moment, like just hours ago, good girl, your new special, went out to the

world. Yeah. What does that feel like? Because I know you've worked on it for two years. Yeah. You know, a hundred or something more shows just trying to get it right. And now everyone gets to see it. It's, if they were up to me, I feel like stand-up would never be recorded for people to consume. Because I just feel like it's something that I develop in these rooms where it feels intimate. It feels like we're just friends sharing almost like inside jokes. And I'm saying things that I don't want to leave, I don't want this to leave this room. So it's, I don't even think about what I'm developing the material that people are going to see this, like, be able to stream it and comment on it and analyze it. And so it's always, it's always kind of hard for me to put it out because I'm like, oh,

I maybe should have thought a little bit more about not saying so much. But I really have no choice because that's what the act becomes when you're on the road and you feel that free. And so it's, it's vulnerable. It's too late to say I shouldn't have said that much. It's out there. And you said a lot. I really did. And I don't even want to think about what I said, to be honest with you.

It's just like out there. It's none of my business now. and I just, it will haunt me the rest of my life, I'm sure, with people quoting it back to me. But yeah, you know, it's a snapshot of like what I was feeling for those two years and what I was thinking. And will I stand by it in a couple years? I don't know.

But this is where I'm at now. I don't think people truly appreciate what goes into these because they think, oh, she's so funny. She got up there on the stage and St. Louis, home crowd and just did her things. But like, the work. Yeah. And, like, you sweat every word.

I know you do it. And every beat in a joke. a pause before you say the next thing. Yes. Can you just describe a little bit for people who don't get it? Like, what goes into that one hour? I mean, you know, it starts out just going on the road and just feeling it out. And I mean, it's a little bit freer when you're just developing material. And audiences really like it to go on that journey with you of like, oh, well, that didn't work.

And I'm going to try this new thing. And you're writing constantly on the road. And then you get to the point, you know, six months out from a special. And you're like, okay, now I have to focus. And now I have to say it in a specific order and figure out how this, there's like a narrative. And you have to, I think about specials now differently as not just like, here's all my jokes, but what am I trying to say? What is this saying about me and my life right now? And how do I make a piece of art? I don't think I ever approached it really that way before. I want these to be standalone of like a snapshot of my career in this moment. So it's really about being meticulous about, you know, just, I'm just someone who loves a lot of jokes. I like watching 30 Rock. I like watching Veep. I like watching shows where it's like if you sneeze, you miss a line. I like being stressed out that I might miss something. So I try to just, I like joke density.

So it's, it's, you know, it probably aggravates everyone that works with me where I'm just like, I just feel like this isn't funny. And they're like, it is. Just let it go. You don't want to tag everything, but I just, I want the jokes to keep going. I just, I don't ever want to look back and say, oh, my gosh, I miss that one line that could have been funnier. Like, there's one line that I've written since the special that goes into one of the jokes that is like my favorite line of the, joke now, and I'll never, I'll never do it.

Right. It'll never see the light of day because I can't do these jokes anymore on the road because they're out there. And so there's like heartbreaking moments like that. So I just always try ahead of a special to just counteract any kind of regret I might have afterwards, which is impossible because there's always going to be something. But it's, I'm crazy when it's leading up to a special. Like, it's all I'm thinking about writing it all out, twailing over notes, having my

friends watch it and give their notes on it. Yeah, and it's just, I just feel like, you know, I'm at this level now where I could probably coast a little bit and good would be good enough. And I've seen people do that before and it works out for them. But I just, I don't feel, I never feel like I've arrived. You know, I feel like I'm always just still having to prove myself. And I don't want to lose that kind of drive? But don't you think that's the edge that keeps you where you are? Because I think a lot of people, you're right.

They get to a certain point, they're like, I did it. I think I feel this way, too. That just doesn't exist. You have to keep going because that's the thing that got you there. Yeah, I would really stop. If I felt like I got to a place in my career where it was enough, I wouldn't do this anymore. I'm doing this because I'm feeling not enough. That is what drives me.

I don't feel good enough. I don't feel talented enough. I don't feel accepted. I don't feel like people see me or understand me. And if I got to a place where I really believed in myself, I really would probably just retire. So I'm glad that I don't feel that way because I do love the work. Is that still true? Honestly, the fact that you're going to, this special is going to be a hit.

You just came last night from doing the Time 100. You're on the cover of Time magazine. You've done the globes twice. You were the star of the roast of Tom Brady. I could go on and on and on and on. You're in this movie that's coming up. You really still feel like you haven't made it in some way? Well, I feel like I've made it because it's like the evidence is there

that that's all things that's happened to someone who's made it. But do I feel like I've tricked everyone to get all those things? Yes. Do I feel like I've done something deceptive or that maybe some of my success I can attribute to something other than just talent or hard work or that? Or that I'm lucky. And in many ways I am. And there's something to be said for that. But I just think, yeah, I struggle with the imposter syndrome thing.

I'm constantly watching YouTube videos on it to how to overcome it. But then the more I think about it, I'm like, I don't want to overcome it. It is what drives me. I don't really like artists that, like, think so highly of themselves. I'm not drawn to that, and I want to be the kind of artist that I guess I would be drawn to, which is someone who's secure and their insecurities. And a little fear that it's all going to go away tomorrow. Yeah.

I like to live that way a little bit, too. You let your guard down, it's going away. Because it can. Yeah. People say to me all the time, no, it won't. It's never going to go away. And I go, name one person who's hugely famous that hasn't had a little bit of a drop-off. because even a little bit feels like something

when you've been on the top, you know? Like, it will happen eventually. You know, your star fades and you have to reinvent and you have to go away for a little bit because people get kind of sick of you. Even doing all of this press right now for my special, I'm like, I'm going to have to pull away because the tide can very quickly turn from,

we love her, oh my God, I can't wait to see her on this to like, enough. It's happened to me with people. You know, it just, so I'm aware of that and I know that other shoe can drop and I'm terrified of it, But at the same time, it's like death. Another thing I'm terrified of, it is inevitable.

There will be a death of this career. And it probably will be in line, I think, with my own deaths because I don't think I'll ever stop. Right. But yeah, I think it's imminent. Well, you're just listening to you, this is the work ethic that got you where you are. But it's a long road. People are like, oh, yeah, I saw her on the roast of Tom Brady. She's new.

She's awesome. And I'm like, dude, did you see the roast of Roblo and Alec Baldwin and all the others? And the stand-up she's been doing. So when people come up to you and say, wow, you're amazing because they've just discovered you, does it feel like, man, you have no idea what it took to get to the roast of Tom Brady? No, I don't mind it. You know, like, I feel like everyone kind of discovers me at their own pace. And some people are like, I've loved you since the beginning, since Tom Brady.

You know, like, there are people that give themselves that credit of being an OG. But, you know, I think I kind of like sometimes that people think, like, that I'm just naturally this good and that it hasn't been, you know, it hasn't been 22 years leading up to this moment. That's, that's, and that's another way that I think that I've tricked people sometimes is that I'm like, oh, no, you need, you should know everything. This, I tried so hard to get to this place. And it isn't just natural for me. In some ways it is. I have an affinity for performing and, and being funny, but it's been a lot of work to do what I do. And sometimes I don't like to reveal all the work because I want people to think, oh, she's just a natural.

But like Taylor's stuff said, I've never been a natural. All I do is try, try, try. Yeah. When you stand in that room last night at the Time 100, and you are one of the people on the cover of Time magazine, and then you were hosting, and you're the person up there in that room, is that at least a moment where you can go, okay, I belong in this room, or at least I've earned my way into this room, because that's a huge deal. It is a huge deal. I trust the people that have told me that I belong there, that I belong there. So I kind of go off of that feeling. I think internally I'm probably like, this is ridiculous.

But I also like that I can approach these things with like, I can't believe I'm performing in front of Benicio del Toro and Victoria and Victoria and some scientist who, you know, is curing malaria. Like, it's like this is ridiculous and almost like a make-a-wish moment of like these are my wildest dream. So there's something that I like having that feeling of like, you know, I remember being backstage last night and thinking just you're great. You deserve this. You're going to kill it. You're ready. Like trying to psych myself up and try to see myself the way other people see me. I try to do that. But do I believe it? I don't know. I do know that I do know that I deserve based on the work that I've put in to be where I am. So I will say that. Like I have put in the work. care a lot about making it good. Clearly. Yeah. Yeah. So the special takes place at the Fox Theater in your hometown of St. Louis. That had to be incredibly special to walk out there to a packed venue on this really important night for you and get the kind of reception you got there. Yeah. I mean, there's a part of me that I feel like always was drawn to wanting to be a performer and maybe be famous. Even back in high school thinking, none of these people think I'm that special.

I just didn't feel in high school that I had any talent. There was nothing I was exceptional at, and I was just dying to be seen, and for, you know, to get attention. And so I think there's a part of me that was always like, I'm going to show these people someday. Like, I'm going to be someone. I had no idea how at that time, and I think I lost hope at some point that there was going to be something that would get me there. So there is a little moment of like, I made it. You said I wouldn't. But the reception, you just, they're not like that there.

They're not, like, judging me based on high school. They're just, it was so warm. Everyone's just so excited that I'm from St. Louis, that I live there, that I represent the town. And they're really, you know, as a girl from St. Louis, I'm always proud of our celebrity. Like, John Hamm, Sterling Kay Brown, you know, like, Jackie Joyner-Curcy. And it's like, so to be on that list of St. Louisans that they can be proud of and be like, she's from here. And she lives here. It feels really good.

Nellie. Nellie, that's great. Yeah, Nellie, of course. Put us on the map. Yeah. In that audience, in the front row, your parents who are also here today, Hi, Mom and Dad. There they are. Yeah. Are they always front row at everything? Yeah. As much as I can bring them along, yes. They're just, they get such a kick out of everything that I do. They are so proud of me. They are the reason that I was ever able to do any of this. It's not even, there was never a moment where they said, consider some other, you know, avenue. Because it wasn't working for me for a really long time. I mean, I remember when I first started doing stand-up, and it wasn't going great. There was little things here and there, and I was really enjoying myself, but it was like,

I was probably 24, and I was maybe, you know, I guess five years in at that point. And I just said to my parents, give me to them 27. Please, like, just support me till I'm 27. Like, if I need a little cash here and there, I promise you can cut me off after that. And I was so grateful that they did something. support me and so that. And it was on the eve of my 27th birthday that I got my first TV show. And I was now going to be independently making my own money. So I really timed it perfectly. My dad always marvels at that. Like, how did you know? And I think I just, I never assumed that

this was going to come easy. Like any kind of big thing I got early on, I was on last come of standing when I was 20. I got the Tonight Show when I was 24. I remember thinking, this is too soon. I'm not ready for this. Oh, interesting. Like, I hope I don't break right now because I can't, I don't have, I don't have the chops yet. Because stand-up, you just, you kind of, you don't come out of the gate great. It is so, there's maybe one or two people I can even think of that were just great from the get-go. Eddie Murphy and Chappelle are the ones that I'm like, oh, I think the first time they went on stage, they were just, you just knew it. But it takes about 10 years to get good at stand-up.

So I knew, I was like, I'll do about nine years, I think. And I was right. Yeah. So, but they're just, they're my best friends. and they're still so with it and so cool and so funny that, you know, as long as I have them here, I want them around me as much as possible. I learned from Kathy Griffin, like when she would bring her mom on her show and hang out with her in an old age, I was just like, I want their relationship.

And I was, I think I always kind of rolled my eyes at people that said, oh, my mom is my best friend. And I was just like, oh, you guys just like, she gets wasted with you. Like, that's kind of always what I, and I kind of was like, oh, that's such a weird thing to say. And now I really get it. Like, my parents are, like, my best friends. I, like, hang out with them more than anyone. That's so sweet.

They're so fun. They're so hip. I don't have to censor myself at all. Oh, I noticed. Yeah, you know. Yeah. Yeah. I noticed.

They just get it. They're really hip. And they've, and they are, they made my, um, they developed my sense of humor. They exposed me to the right things, probably too early for some stuff. But, like, I remember coming home from school in ninth grade. And my dad said, you have to watch this. And you put in a VH. test tape. He had recorded Conan O'Brien's

fifth anniversary special the night before. And I had not even really been paying attention. And he just knew I would love it and he was so spot on. I mean, being a Conan O'Brien fan has changed my life. And my dad knew that this was something I was going to like. It wasn't for my sister. It wasn't for anyone. My mom, it was

for me. And I just felt so seen and that changed, watching that special, like, changed my life. Like, I was just like, you can be so weird and so smart and so silly, but still, like, you can tell he's so smart. That's what I really was like.

I love this. What a gift from dad. What a gift. And always, like, Seinfeld, we're a, you know, huge Seinfeld house. Like, I just, I think, you know, the stuff you watch and consume growing up really shapes who you become. And I got just exposed to the coolest stuff. I'm so grateful. Hey, guys, thanks for listening to the Sunday Sit Down podcast.

Stick around to hear more from Nikki Glazer right after the break. Welcome back now more of my conversation with Nikki Glazer. There's a moment in good girl, and I'm not going to give it away, because it's almost like a twist in the narrative you're building. Yeah. But your parents are there in the front row we come to learn. Yes. I think I know the answer to this question, but is there anything you won't say in front of your parents? Because on that stage, it certainly appeared not.

You know, on that night, no. And I even told them, like, listen, usually when they come to my live shows, I will literally say into the microphone, hey, dad, you might want to go out to the the merch booth and get a t-shirt right now for the next 15 minutes, I think you'll be safe. I give them a heads up. I didn't use to, I used to have no filter. I just didn't care. I couldn't even imagine putting that in my mind to hinder me as an artist. Like, it's up to them to want to come. And if they're signing up for it, like, they have to just take it. And then I think as I got older, I was like, oh, I could see it from their side of it. And I was like, this might be really tough for them. So I have more empathy now, and I warn them. But for the special, I couldn't

really tell them to leave because we were at a taping. So I was like, you're just going to sit through it. And I just had to disassociate. And they do too. Like, I think they just have to, hopefully they see me up in the lights and they're not seeing their daughter. They're just seeing this, like, superstar that is kind of not, you know, someone they gave birth to. Clearly no inhibitions as your dad is staring up at you from the front row. Yes. It's, but you know what? Like, I feel like they're pride in me and like over what I've made from telling all these shameful details about my life and my sex life. It's been really nice to show them that you can be shameful and say things that you should

would think that no one would like you because you think these things. But I'm like, people do like me because of it. And I think it's made my mom more free and honest and open and hilarious. And I think, and my dad has definitely taken some liberties. I mean, it's made me uncomfortable. He's giving it back to me now. The other day we were driving and there was like two dragon. flies on the windshield, like mating, you know, like they're like hooked up, you know, as you see.

And my dad was like, oh, look at that. And I was like, oh, my God, it's so cool. They're mating. And my dad, I'm so horny right now. And I was just like, dad, he was like cracking up. He's like, listen, I can dish it too. And I was like, oh, God. What have I made? What have I made of you? See, that's how you make him feel. Exactly. And fair enough. But like, like, I did understand, like, oh, that's, that, that does feel horrible to hear. They're good sports to say the least. They're such good sports. So you mentioned Conan, all that inspiration growing up in St. Louis.

There's one thing to be a fan of comedy and then another thing to say, I'm going to try this. Yes. Is that moment at University of Kansas when you see the flyer on the wall? Yeah, that was, no, it was, I went to the University of Colorado my freshman year. And I'd always love comedy, but I just thought the only way to ever be on TV was to be an actress. I just didn't think about the business or like any kind of other avenue besides singer or actress or dancer. And I couldn't really, wasn't exceptional at any of them. And so I was just so bummed out and trying to figure out my life.

I was kind of in the throes of a crazy eating disorder. And I just thought my life was kind of over. This is what it's going to be. I'm probably going to die of this thing. I just didn't, I wanted, my whole dream was to like be on TV and perform. And there was just, I wasn't good at any of the things that got you to do it. So I was just kind of wasting away. And then I went to school.

And because of the way I looked, because of my eating disorder, I really, it was struggling to make friends because I just, it was very apparent. I was struggling. And I think I sensed that. And so I just turned up my personality, like a lot. Like, I just became a lot funnier than I had ever been before. And just so I could make friends and make people forget about what they were looking at. And it worked.

I got so many friends. And they all told me later on, like, oh, people would come to us and say, say we're so concerned about Nikki, and we'd go, oh my God, I forgot that she even looked that way because I was able to really mask it with how funny I was being. And that was the first time I started hearing, like, you should be a comedian. And I just was like, I mean, I was desperate for any kind of direction. So I was like, what? Can I even do that? Like, I just hadn't really thought about it. And it was just a simple Google search of like female stand up and then seeing you know, Wendy Liebman and Sarah Silverman. And then I, sitting in my dorm room in my freshman year was

just like, this is what I'm going to do. And there was a comedy competition on campus. My friend stole a flyer, and she was like, you're doing this. And I was like, I guess no one else is because you stole a flyer. But, and so I just started writing jokes. And then I did it. And the first time I did it, my, you know, my dad was on speakerphone listening. My friend called him from the audience. And I mean, it really, it was one of those crazy. It sounds like it's from like a lifetime movie, but I got offstage. And, you know, I was really down and out at this time of my life. And I called my dad backstage. And was just like, I know what? what I want to do. I'm going to be a comedian. And I just knew. And it was like, okay, well, let's

just, let's figure out this eating disorder because this is going to stand in my way. Like, that was my only obsession before. And now I have a new obsession. And it really saved my life. Like, it just gave me something to live for. And I became obsessed. That's incredible. And you're like 18 years old at that point? Yeah. Wow. Yeah. So it literally changed your life in that moments. Like, saved my life. I really was kind of going to die, I think. Like, I just wanted to. It was just my life, I just didn't, that sounds ridiculous to say now that if I couldn't be a performer, there's nothing to live for, but I really felt that way. And so I, and I was, you know, really sick. And so my life was miserable. So I was just like, please just, let's just get this

over with. And then it was just, I just needed something to care about and something to feel like I had a purpose. And suddenly this, it just landed on my desk. And it was like, oh, and then I completely shifted. And that. became my obsession. That's amazing. So did you feel yourself getting physically better as you guys into comedy? Well, I went to a doctor, like, immediately after, like, I went to a counselor on campus that I had been avoiding going to. And I was like, how do I get over this? Like, it was my first time that I was like, I want to get over this. Like, because I was really into it at the time. You know, like, when you have an eating disorder, it's like, it's your obsession and it's all that I wanted to do. But suddenly there was something else I cared about more. So I just reached out for help and figure it and was like, how do I beat this? And it took, I mean, it was years and years of things of. clawing my way out of it, but stand up in the drive to be good at this thing that I liked so much and saw the potential in being good at was the reason I was able to get out of it. That's incredible. Yeah.

So from that point forward, is there any moment along the way where you're like, I'm not going to do stand-up? Like, did it get, was the grind too hard? Did you feel like I'm never going to make it? I'm scratching out a living, going from one club to the next? Or were you always just locked in on this? There was just no other option. the only thing I've ever been good at. Like, you know, I wasn't great at the beginning, like, because no one is, but it was the first time I was like, I'm better at most people who are starting

out at this. I have, there's something, I have a knack for this. So there was no other option. And I always was really logical about it. I just, I think I researched enough to know that you aren't going to be great for 10 years. So there was no pressure on myself for those 10 years except just go to every open mic, write with your friends, get on stage at any chance you get. And just be patient. So I think I can recall one moment bombing in a bar in Topeka and sitting on the stoop outside and calling my mom and just saying like, what am I doing? I shouldn't do this. But that is, I only remember it because it's the only time ever even entered into my mind.

And I think I was just saying it. So she would be like, no, you're going to. And I knew I was going to keep going. There was just really no other option. Yeah. Yeah. And I was patient. When did you start to feel like this is working?

I know you say it's a 10-year thing. Yeah. So if you start when you're 18, is there a marker for you where you go, oh, yeah, I can do this and make a living, maybe even for the rest of my life doing this? Now, this is like in opposition to what I was saying before about having imposter syndrome, but I just always knew I was right where I should be. Like I was always, I felt like, you know, even like I would, at the open mics, I was like, I'm having, you know, some of the best sets of the open mics. That felt like, okay, I've made it. Then I was, okay, I got the Tonight Show. I felt like I made it.

Like, it was always just right where I was. But, I mean, I guess, you know, getting past here at the comedy seller, I think was a big moment for me. I was my first time living in New York. I was, you know, I'd done the L.A. scene. I'd been in St. Louis developing. And then I moved here, and it was very intimidating. And I felt like, am I going to fit in? This is, like, a higher level of, like, more cerebral, more, like, just, just comedians who treat it, like, a real art here,

as opposed to, like, something in addition to their acting career. or just trying to get them a TV show, people only want to be stand-ups in this town. And so when I was here, I was really intimidated, and I think I was here for a few months before I got my audition here. And I think, you know, sitting back at that bar being so nervous, and it was just like,

you're going to go up tonight and just figuring out my set and going downstairs and having this one shot to perform in front of Esty who, you know, passes you or fails you. And then getting and her just being like, okay, I will take your number. and like being like like like and it's not even like your past it's like I'll take your number I'm like am I past but like and then putting getting those first spots here yeah I think what like even being here reminds me of what that meant to me because there's no denying that if you work here like you're a you're a standup yeah and that like whether you're famous or not when you work here but you're like a tried and true standup and you have the respect of all your peers I think yeah so for people watching or listening to the podcast we're sitting in the olive tree cafe yes which is above the comedy seller yes Fair to say, one of the most famous comedy venues in the world.

Agreed. Yes, absolutely. So what does it mean to a comedian to get, even if it's five minutes, on the stage downstairs? I mean, it just means acceptance into this really cool club. I mean, this is the coolest club, comedy club there is. It's all the coolest comics hang out here, just the best comics. Everyone has such reverence for this place. Everyone's on time for their spots. You know, even like, you know, Chris Rock will get nervous if he's running five minutes late because this place runs very efficiently.

and you have to respect it. And it's like, it means everything. Because it is, and it's also a spot where you feel like you get accepted into like a family. You can just stop by here anytime if you don't have a set. I can be gone from here for years and come back in and I still know everyone. It still looks the same. The menu's still great. And you can get your booth and the crowds are always so hot.

And yeah, but it's, but I, you never lose that feeling of like, hi, is it okay if I get on? Like, no, there's no level that I'll ever reach where I'll feel like I can just walk in here and own the place or something. Like, there's just a deep respect for it. We were talking when you walked in about that booth in the corner. Yeah, in the back. Which is, like, when you walk in here, like, that's where Chris Rock might be or Seinfeld or name your big comedian, would be back there. And you still feel a little like, should I be back in that corner? Oh, always.

Always. I kind of tiptoe back there and maybe, like, put my purse down. Like, I'm so sorry. And they're like, sit down. And then I'm like nervous the whole time. I mean, it's anxiety induced. back there because it is like the best comedians.

And then also like their celebrity friends will just drive by. They'll be like, you know, Paul McCartney's been back there for sure. You know, models, scientists. Like, it's really, it's, it's, it's really intimidating back there. But it's so cool that they all just sit back here

in this public space that if you are someone who's just at the show, you can come up here and have dinner and watch all these people back there, just hanging out. I think it's, everyone feels safe back there. They're not They're not behind frosted blasts. It's like the biggest celebrities in the world just being normal and having the best time and busting each other's balls. It's more fun for me to sit back and observe.

I'm always like in this booth just like kind of walking. And maybe I'll get summoned over and say hi. But I think you're ready now. I think it's time. I'm maybe. This summer. You're still like, oh. I'm moving back here the summer.

And so I'll be here like every single night. So yeah, I'll probably, I'll try to, I'll try to fit in there. Do a test run, see how it goes. Yeah. And then you'll know if it's not. But it's just, it doesn't, that doesn't go away. Like, I'm sure you have things like that, too, where you just still, how you come into some place is how you'll feel there the rest of your career. Yeah.

That's exactly right. Yeah. In addition to your stand-up, you're all well known for the roasts. Yeah. The Comedy Central Roasts, those early ones I mentioned, and then, of course, leading up to the Tom Brady Roast, which I think it's fair to say. It was almost exactly two years ago, by the way. It was two years ago next week, like, just set your career ablaze. Yes.

So when you approach those, whether it's. Alec Baldwin or Tom Brady, what is your approach to those? Because one of the things I, one of the reasons I think they work so well as you'll say, like, I love you so much. After like there's an affection, like we all understand that this is a little bit of a game. Yes. And it's weird because I don't know these people. And I go into a lot of these rows not really knowing their body of work or, you know, with Tom Brady, I knew obviously of him and what he meant to people that. cared about football, but I don't care about football, and I don't really know why he's so great. So I just had to do my research and read his book and watch all of his interviews and just get to a place where I was like, oh my God, Tom, Brady, like where I believed in it. And I understood how great he was so that I can then dismantle him. Like, you have to have the respect and like the awe first, and then I can take him down. I'm kind of uncomfortable taking down people or roasting people that I don't like or that I don't respect. It feels,

I just don't think the anger or the kind of resentment that comes out in my tone is attractive or something that is as watchable as when I'm just coming from a place of love. So I try to get to that place of love. So it starts with a lot of research. And then it's about, then I just watch roast constantly just to get in the mindset because it's just there's, there's no other place like it where you can just say such awful things to people's faces. I really think it is like the most, the safest place for free speech that we have is a roast. Because the things that get said, they can't be said. You would be canceled for saying them anywhere else.

But you have a license. It's your job to go there. That's what I love is like no one can be mad at what I say or that I took it too far or they shouldn't be because that is the job. And everyone kind of agrees to that and knows that. So I love that freedom of being like, yeah, I just said this horrible thing, but you can't be mad at me. That's what I'm being paid to do. Right. Because I probably have the instincts to be like as mean as that normally, but I can't because that would be mean.

But this is, I love when being means the job. And I think it also, I try to approach it from, I think the best roasters are super critical of themselves and are roasting themselves. So I, you know, roast myself every day and think the meanest things about myself. And, you know, I have a lot of, I'm self-effacing to a degree that, like, scares. my friends and family when they hear me talk about myself. And I think I just try to, you know, I just project that. So it's, I just try to think of what can I say about this person that they've never even, they didn't even know that I could go there where they, they almost wish, like,

I would have given a note that she can't talk about that thing. Like I feel like I sometimes surprise people of like, I didn't even think anyone would ever have the balls to say, to joke about that thing. Otherwise, I would have, I didn't even think ahead of time to say, joke about that because who would be crazy enough to joke about it. But I'm like, but if you didn't, if you give me a parameter, I'll stick to it. But if you don't, I'll do it. And I have before. I mean, it's been, I've been at Rose backstage, like, right before we're going on where I get a note from the network of like, hey, so-and-so heard there might be a joke like this, which is one of my

jokes, in the set, they're going to walk off stage that is reference. And I go, well, that would have been nice to know a week ago. But, okay, now we have to rearrange everything. But I do respect it. I don't want to, you know, I don't think Rose should just be like, you got to, you got to take whatever. We're dish in. Like, you should be able to have boundaries, but it's fun to find loopholes. I mean, do you, I think part of the joy of it for us, and it's a real study in human nature, is you are saying things that people think but would never say out loud. Yeah. To Tom Brady in particular. Yeah. About Giselle and all that stuff. Yeah. Is there any inner cringe for you when you're saying it? Or are you just like, I'm here.

I've got to go all in on it. Well, when I'm doing it, no. Like, I've got to be that person that is, you know, just sticking the landing on these and, like, believes that what I'm saying is appropriate and okay to say. But, you know, if I come across a clip online of myself, I go past it right away.

The times that I've had to watch them or been on a radio show and they play it, I just am like, what are you saying? How dare you say this to this person you don't know? Like, I really have that reaction of, like, there's something wrong with you. Like, I really, there is a cringe element to some of it. And I will say I pull back.

a lot. People might not think I do, but there's been times that I have left some, I've left some of my best work on the cutting room floor because I just didn't want to hurt someone's feelings. So I do, I want, I don't want anyone to be regretful that they did the roast. Maybe besides Anne Colter. I actually was thinking about that as one. I didn't mind if she didn't like me after it, but everyone else, I just want, I don't want to have to, like, avoid them the rest of my career. Right. And everyone's been pretty good sport. Yeah. And as you've seen, as you've seen, said many times, whether it's there at the Golden Gloves, the reaction of the people is key. It's everything. Whether it's Kevin Hart or Tom Brady or Leonardo or DiCaprio, you've got to have that.

It's everything. People don't realize how much we base our opinion about something off of how other people perceive it. So whether it's a comment you're reading under a video you're about to watch online. I mean, I do it too before I watch a video. I'll be like, what are people think about this before I form my opinion? Or a laugh track. Like, we think laugh tracks are ridiculous, but when they're not there, This is spooky. We need to be shown how to feel. So we need to see that person laugh when the camera lands on them.

And I know every single host that people have said have bombed or didn't do well. If you just put a laugh, if Tom Hanks would have laughed at Ricky Jervais's joke in that moment, it would have been like Ricky killed

and didn't go too far. And, you know, Ricky's obviously killed and everyone loved it. But like there are moments that I remember of people having uncomfortable reactions that completely changed

the way people perceived the entire performance just because of one joke. Right. There's one joke that I wrote for a friend one time that did a roast, and they got so much backlash for it because the person that it was about, they just, they maybe weren't even listening, but they just kind of looked like, they looked upset, and it was like, they went too, like, that was the headline. Right. And it was so ridiculous because the joke was not offensive at all, but they just heard one

buzzword in the guy's face, and that's it. Then you're done for. And that's what's scary about this stuff is that it's so sensitive. that just the one mistake you make or one reaction shot you get can change all of the headlines about whether you killed or didn't kill. Or like, you know, people always say, you tow the line perfectly. And it's like, but that isn't even up to me. I've gotten really lucky with people's, you know,

there's effort that goes into it of, you know, saying, I love you so much and building them up before I go in for the hit. And that's maybe a little calculated. But I always try to make those moments actually very sincere. I don't want to like butter someone else that I don't actually am not a fan of. And I think that's why the Globes worked because you played it so well, especially that first time. So you're coming off the Brady roast. Yeah.

Oh my God. You're on fire and people are like, all right, how's this going to go over though in that room? Yeah. It's all elegance and movie stars. Is she going to really go in that way? Yeah. So that first time, how did you approach that one maybe differently than a roast of. Oh, that was terrified because I knew I knew how I would feel if I was a celebrity watching this girl that just,

did that at the Tom Brady roast and just went for the jugular every single time, I would have been terrified being in that audience. So I knew that going in. And so I really, I set up the set to, you know, build in intensity so that I would ease them into like, okay, she's going to take care of us. She knows the limit. She's not going there. And then save maybe some more harsher jokes for the end. But I really, and it was also about, like, don't walk out there like you. deserve to be there, like humble yourself in front of these people, win them over by letting them know that you don't think you're one of them. And I think I got that advice from, I think it was Ricky who told me like you aren't one of them. You're not an A-lister. And no offense, but we're

comedians, we're clowns. And they want to feel like you are just so in awe of them. And I literally am. I can't believe I'm there. So it was easy for me to tap into that. And you just, but so much thought went into that. I mean, it was, it was so hard because some of the best jokes you just couldn't tell that year, because it just, I hadn't earned it yet. And then you got the second year, I could walk out there and I, I sensed that their faces weren't as like, like, pained. There was a little bit more leaning in of like, I hope she might talk about me. And that was just, it was so nice to see that I, like, gain their trust, like a, like, you know, a shelter dog or something. And that's how it felt. Like, I really, they were suddenly eating out of my hand. And that felt like,

oh, I really, that felt good. I will say that I will give myself a lot of credit for that because that took a lot of engineering and a lot of thought and just precision to nail that. It was perfect. Thank you. Because that is a thing, isn't it? Because I felt that sometimes too. Do I have permission to say these things to these people who are like, who are you?

You know, that kind of? So you did play that. Like, I get it. I'm the outsider coming into your world. I'm the Joker. That might be beheaded after this. Yes. I'm visiting, I come in peace, but my job is to give the audience at home what they want,

which is like some take down of these celebrities who think they're so cool and are on these pedestals. Like as much as we love celebrities, we just can't stand how cool they think they are. And so you have to deliver that to the audience at home. But it is a fine line between, because no one in that room feels that way about celebrities. And so it's threading that needle's tough, but I was really proud of how I did. The other thing I didn't realize is you send flowers and handwritten cards to all of the targets in the room after the Golden Globes. Yeah. I did that this year for the first time. Did you?

Yeah. I just felt like they were a part of it and that they, it wasn't even about like sucking up to them. I feel like it can maybe look like that, but it was about just being like, thank you. Because you're the reason why people are saying I killed. Like you being cool in that moment that maybe you didn't think that joke was that fun. and maybe it made you uncomfortable, or maybe it made you feel insecure about this thing you're insecure about, um, you,

you didn't do the thing that you easily could have done, which is like, just be like, uh-uh. You know, like, it's, it means so much to me.

So I just wanted to thank them for being cool. And also for like, taking opportunity to like, I'm giving, I think it's, it makes us like, when celebrities can laugh at themselves, we like them more.

So I'm giving these celebrities an opportunity to be more likable to the American public. And I, I think they're all catching on to that's, it's a cooler look to be cool about it. And yeah, I just wanted to say thank you. And Leo sent you something back? Yeah, yeah, yeah, he did. He sent me, I made a joke about him saying in an interview in a Teen Beat magazine in

1991 that his favorite food is pasta, pasta, and more pasta. I go, is that still your favorite food? And he was like, you know, memed it. And yeah, he sent me back three baskets of pasta. Pasta, pasta, and more pasta. So funny. That's good. so sweet, didn't expect any reply at all from anyone.

Like, I thought their assistants would just get these flowers. Like, I didn't even know if it would get to them. So the fact that he took time to do that was just meant so much to me. And really showed me that, you know, my whole point of that joke is we don't know anything about you. Like, who are you, you know? And open up a little bit. And I felt like, oh, now I know more about him.

Like, this is a guy that is thoughtful and funny and kind. And I was like, let's see more of that, Leo. So I had to tell everyone that he's like a really good guy. Yeah. Yeah, it was really sweet. That's funny. That's a funny reply, the three bags of pasta. It was so funny.

I didn't even get it at first. I was like, oh, we got pasta. And someone goes, it's pasta, pasta, more pasta. I was like, oh my God, that is so funny. That is so cool. God, he's great. That's very good. Yeah, he's really cool.

That also was a good joke by you because you go, oh, you're doing the young girlfriend thing. Oh, yeah. You're like, I'm not doing that. Yes. I'm doing something else. Well, constructed. I mean, I didn't. I hate going for the easy joke.

Yeah. And the easy joke for Leo is that he dates women under 25. And every version of that joke has been done to death. But in writing those jokes that, you know, we just, me and my team could not crack another angle for Leo. It was so frustrating. And we came up with a really good joke about having a girlfriend and it was working in all the clubs when I was trying it out. I was like, I don't want to do it, you guys. I just, I just for him.

Like, I just don't want him to be like, oh, I have to laugh at another one of these. Because I knew he'd be a good sport, but like, ugh, so cringe. But then it was so, I was able to do that joke just because I knew I had the next thing on hand of like, come on, man, tell us anything about yourself. And that all came out of like, why isn't there anything else we know about him? Open up! And then someone in my writer's room was like, that's the angle. And then we went off on that. It was really fun.

Really good. Very well done. Thank you. Stick around for more of my conversation with Nikki Glazer right after a quick break. Welcome back now to the rest of my conversation with Nikki. Glaser. I've got to ask you before I let you go about the movie we were just talking about, Fifth Wheel, you and Kim Kardashian, Eva Longoria directing, Judd Apatow's involved. No, no, no, no, no. He's not involved at all in that one. Okay, that's the other one.

Yes. So how did that come about and how are you finding acting? Oh my God. That came about. I read this script that was written by Paul Appel and Janine Brito, like over a year ago. And I was just getting to the point where people were starting to be like, you should read scripts. I didn't, was like, for what, to give notes on them, like, to punch them up? And I'm like, oh, to be in them? And so I read the script and it was my favorite thing I had read. It was, I was just like, oh, my God, I can't wait to watch this movie. This is, like, the next bridesmaids.

And I was thinking maybe I could be, like, a waiter in it or something, like, do a cameo. Like, I just did not even think I was being considered for, like, a lead role. And then I met with producers and said, I love this movie. I was just, like, congratulating them on, like, what, I can't wait to watch this. And then I thought it had been casted. I thought they were already shooting it. And then nine months later, they were like, and so you got one of the lead roles of Lexi,

and I was just like, are you kidding? Like, and it was, it was honestly so insane, Willie, because I didn't audition for it. There's really no evidence of my acting really anywhere out there. And I got on set the first day, and maybe it was a week into filming, that I just turned to Eva at one point, or someone on set, and I said,

I go, you guys have no idea if I, if I could act, right? Like, this was the biggest gamble you could have ever taken. Like, what, but this is what happens when you get famous. People just give you things that you've been, that people work so hard to get. And then they just suddenly fall in your lap. So it was so funny to me, I got a lead role when no, I mean,

they'd see me on SNL, I guess, and they had seen me in a couple, I'd get in a couple scenes and movies and stuff, but to carry a film. And luckily, they were like, they all, they admitted to me later, like, after the table read, they all were like, oh, thank God. She can do this. And so it was. But it was just kind of an example of how when you get to a certain level in this industry, like things that you thought would be so hard to get kind of just like people give them to you.

And it's not fair at all. And I feel bad to the actors who struggle so much and would kill for that role and do something with it that I could never even do. But I get it because I'm hot right now. That's just the way it works. And it sucks. It sucks. But not for me in this moment. But it was really, it was so fun.

It was just fun to, you know, stand up as such a solitary pursuit. And you just feel like you're just a. alone up there and with your material and it's so personal. And so to collaborate with, you know, all these funny people and to be an ensemble cast. And we really, honestly, it was me, Fortune Feemster, Brenda Song and Kim Kardashian and Eva directing. And we all became like great, great friends. And we had the best time. And it was just so fun to, I don't know, it just felt like I had a little family that I hadn't had in a really long time in this job. Did it go well enough? There might be more in your future. Oh, yeah. It was so fun. I really loved playing a character.

I loved learning about, I don't know, I just, it was different for me. The thing that was tough about it was that after a scene, you don't get laughs when you're performing because everyone has to be quiet on set. And I'm used to like immediate, like, that was funnier or that wasn't. So I'd get done with a scene and be like, I just bombed. And the lighting guys were like, we can't laugh. Like, we're getting trouble. So there was like not that immediate validation you want.

And so that was a little struggle for me. But I really, I loved the process. is because they were really open to me, like, punching things up and pitching jokes. And so I got to be, like, heavily involved with that part of it, which, you know, I didn't even think I would be. So I can't wait to, like, start making movies and being able to have a hand in the writing and stuff. As you say, you've kind of made it at this point. So is there other stuff that you're, like, thinking about it?

I know you like to sing. Is there, like, using this moment that you've worked 22 years to earn? Yeah. Are there other things acting, other things you're interested in? Um, you know, like, I was, I've been watching Survivor this season and I was like, I would like to go on Survivor maybe. Like, there's things like that. Like, they would love to have you on Survivor. But I have to earn it, Willie.

This is the thing. Like, I just jumped in. I watched season one, two, three, and then I'm back at 50. So I have to, to be ingratiated into the Survivor family, you have to like be a super fan. So I have to now go watch, you know, 46 seasons of team. I can't lie, Willie. I don't lie. I can, maybe if there's some good synopsies on YouTube I could watch, but I was thinking like, I, I could maybe, like, because you get to do things when you reach a certain level that you would never dream of getting to do and that would be really hard to get any other way, I might take advantage of that. Like, instead of just getting a table at a restaurant, I'm like, I want to go on Survivor. Maybe they'll let me.

Let's put that out in the atmosphere right now. Mike liked it, but he's a super fan. Yeah. So he earned it. And everyone in the Survivor community is like, you deserve to be here. So I just, I want to earn it a bit more. And then I think I would like to do it. Okay. Yeah. So that's the big showbiz goal. Survivor. Survivor. And then, like, my, I don't really think in goals that I never really have.

I truly haven't. But if I'm putting one out there, I would like to be in a Taylor Swift music video someday. I'm just, like, the biggest Swifty. And I just, I love the way she directs. And I would just like to be directed by Taylor Swift and to, like, be a part of her, you know, videography at some point. And she tends to, like, put, you know, celebrities cameos and comedians. And so I think that's a goal. I would never, like, approach her.

with her anything and I would be embarrassed if she ever saw this clip, but I'm just, I'm manifesting it to like, that, that would be something that I would just, you know, die to do. I'm going to send it to her team. Please don't. Please don't. She's heard enough from me. Nikki was begging to be in one of your videos. No, no. Only if you would like, wait, have you ever connected with her since you're like such a well-known, swifty? Peripher. Like, like, through things. Like, she's sent me, like, you know, the boxes and stuff that, like, that you get ahead of, so, like, she's aware of me and, and so sweet. And yes. But, but, but, It's too overwhelming. I don't need to...

Now you're getting shy all of a sudden. I honestly am blush. This is the only thing where I will get a little bit cagey because I just want to be respectful and like I never want to be someone who's like trying to get into her circle or something. Like I wanted to happen naturally if it ever happens and not because I'm like snuck my way in or... Smart play. Yeah. But also you want to be in her video. Just her videos. Like she doesn't even have to be my friend. Like I'm not asking for for much and I'll do my best and she can cut me out of it. I just want to, I just want to watch her work. She doesn't even have to be there that day.

No, she has to. I want to be directed by her. I think she's, I want to watch, you know, I just like respect her as an artist in all the ways, all the different things that she does. And I really respect her as a director. And I'm like, I just want to, comedically, I want to be directed by her, I think. Okay. I like that.

We're putting some good stuff out there. Yeah. So fun to talk to you, so happy for your success. Thank you, Willie. I, like, truly I've been a fan of yours for so long. It means so much to me. Up on these stages and see everyone get you and get to laugh with you. and see what you've done, it's an awesome thing.

I said to you earlier, it's like watching someone from your high school, like host the Golden Globe. They're like, there she is. I know her. It's true. I think that's... Because I know what that feels like to watch someone where you're like... And I get that a lot where people are like...

And people really will say to me, I'm not happy for most people's success, but I'm happy for yours. And that really means so much to me. And I think that's... I hope that speaks not to only my talent, but like my character of, like, being a kind person. Like, I get a lot from my comedian friends who, who, like, you know, we can all be jealous of each other's success, me included, but people go,

no, you're, you've always been nice to me, you deserve this. And I think that's part of it too, I think. And people are like, no, she can have this. She's a good person. And I think that means a lot to me. And it's the journey to know how many times you waited downstairs to get on stage or clubs across the country. Yes, people who know me have seen how long it's taken and how I haven't ever really reached for something I didn't deserve too soon. I've just, I've been patient and I feel like I've earned it. And I haven't, you know, yeah. I think that means, yeah, that means the most to me when people are like, you deserve this. And I'm happy for your success because that's hard to happen in this business.

A lot of people are just like, oh, her. Why her? She's kidding this? We're happy for success and can't wait to see in Taylor's new video. Yeah. It's going to be great. Thank you, Willie. Thank you, Nikki.

After we sat down in the cafe, Nikki and I hopped up for a little stroll around the neighborhood. This is the neighborhood. Yeah, this is it. this is, uh, what was the, the Dylan movie that came on? Yeah. The, the, a complete unknown. A complete unknown. It's all around here.

With a Chalome. Yeah, Chalome. A salome. Now, did you have that dialed in with Sandler beforehand? I assume, did you know? You know what? No, it was a, like, he was sitting down. It was like probably five minutes until the show started. And one of my producers went up to him and was like, hey, can we?

She's going to maybe call on you. And he goes, no, no, no, don't. This is her now. I don't want to steal focus, maybe not still focus, but this doesn't need to be about me. And we're like, no, she wants it to be. And just, it's real quick. Just, and he nailed it.

I mean, that was such a great moment that, you know, was orchestrated, but very last minute, done. And we could have done, even if you wanted to sit it out, it would have worked, but it was so fun that he was down. And he's been so sweet ever since. And he told me that he can't go anywhere without people saying Shalame to him in the street

like everywhere he goes he hears it multiple times a day and so if that's, it's nice to have that kind of impact on Adam Taylor's time. Yeah, you helped his career. Yeah, you're welcome Adam. Are there some of those are

like the person's not in the seat yet, right? Like at the, at an event or... Oh yeah. And you're like, uh-oh, there's a whole joke built around this person being here. Sometimes it's like, oh my God, are they, are they going to be, are they going to get there too late? Like, I think there was, the first year there was kind of rumors that one person that we were

hitting pretty hard had caught wind in some of my press interviews that maybe I was going to do a joke about them and they were just maybe going to skip it, which would have been, it's smart, you know, like, you just want to avoid some kind of stupid joke. And that was by the, that was the year that I hadn't really proved myself and they were like, what's you going to say? And luckily they showed up in time, but there was like last minute things like that. There was one joke that I had about a huge celebrity that was in the room that. that were for some reason

was sat all the way in the back. And so I had, you know, written in like, why are you back there? Did you buy these on Stubhub or win them in our radio contest? It was a huge lawyer. I don't want to say who it was because it's embarrassing that they would even think to put her back there. But then when I did it at rehearsal,

the producers realized this isn't a good look that we're putting her back there. So they moved her up. And I'm like, damn, we lost that joke. That's what I was thinking. Maybe you told that on Howard the next one. Yeah, yeah, yes, yes, yes. Yeah.

So it's, yeah, you and you have, have to like memorize where everyone's sitting and and kind of think to where to look. Yeah. Also just like who is who's going to be there? Yeah. You know, like who's, they might be nominated, but they aren't going to show up. Right. You know, we are just every day in the writer's room getting, you know, the updates of who's confirmed to show up and just celebrating and being like, yes, we can do that joke.

You know, it's like so much stuff gets left behind because they're just not there. Right. And you can't make fun of someone who's not there. Yes. You know. Thank God. Sean Penn showed up to the global. He doesn't show up to anything else. That was so good. But that was, yeah, we lucked out. And on the... Just smoking openly in the room.

So cool. Yeah, does he have like a waiver on smoking laws? Don't. Him and Chappelle can smoke indoors. They're the only two people. But on the Sean Penn scale, he handled that very well. Oh my God, yes. Right? He was amazing. And I was, that was the one I was nervous about because it was about his looks and you can't make fun of someone's looks. We all know that. And he's an aging man and it was talking about him looking like a sexy leather. handbag or aging into one. And, um, but then I justified it because I was like, I am attracted to him.

I actually, I like this look that he has. And it does look like that. And, um, but the greatest thing was that, um, Kimmel told me, do that joke. He doesn't, he's, he's, he's not vain. Right. It's not going to affect him. Right. I couldn't even understand.

How could you not care about someone thinking you look like a leather handbag? But he didn't. He didn't. He didn't at all. No, he's very secure. That was one where at home, we're all like. Oh, I was. And we're like, okay, good.

That was the part in the set where I could breathe after it. Like, leading up to that, I was just like the Sean Pendock. Like, it's in my head. And as soon as I looked at him, before I said it, I knew he was going to, he was going to like it. Because he was already like. Yeah, a little smirk. Yeah. Just ready for it.

I'm like, oh, he's, he knows what's coming. Right. So you mentioned a joke that didn't make it into the special. Yeah. Do you remember? It was a tag to a larger, but there's a bit in the special about being, I want to be a dad because you can just leave. moms can't leave. There's no deadbeat moms. There's deadbeat dads. And the tag I have now that I wrote right after the special was there's no deadbeat moms. I mean, there's dead moms and there's beat moms,

but there's no dead beat moms. And it sucks because as soon as I wrote it, it was like, I had friends who had to me being like, that dead mom's beat mom's line is the best. And I'm like, I know. And I'm sure people now are like, it's not that great. And there's nowhere else to use it now. Nowhere else, Where could you put it? This is, you know, whenever I'm, forget a line or I have one of those things. Like, why didn't I say that? I go, there's going to be some other use for it. Yeah.

So, exclusive. Big time. A joke right here. We got it here. With Willie Guys. Web Extra. Yes. Love that.

You also like, do you shoot two shows for the specials? Yes. Yeah. We did two separate nights. Usually I do two and one night and it's just rough, like turning the crowd around. And so. It's because you're like, you have it. I mean, I know you've done it for two years, but it's so tight.

Like, you don't miss. There's no, like, flub. There's no, um, there's like, well, I'll take it over if I's flub. Do you? Yeah, I learned that from watching Schumer. First special taping of hers I went to before I was even doing that stuff. She messed up a line. She goes, I'm going to take that over.

I'm like, you can do that. And it's like, of course you can't. It's not going to work for the crowd now because they've already heard it. Right, right. They even like it because it breaks the tension of, like, we're shooting something. Like, the crowds at specials are always the worst. Like, it's such a shame that that that's, how stand-up comedy is mostly seen by people.

They're always the worst crowd because they're so nervous. It's just an energy in the room, no matter what you do to make them feel comfortable and to acknowledge it, they just can't relax in a way that makes them laugh a normal way. There's just a tension in the room that makes you perform differently. And so when you call out that there's a taping and you're like, I flubbed it. Guys, they just suddenly go, oh, she knows too, that this is weird. And so it's actually, it's a good thing to do. This is it.

This is it. My favorite place. Come on. Man. Thank you. After my sit-down conversation with Nikki, I stepped outside to the sidewalk for a chat with Nikki's biggest fans, her proud parents, Julie and E.J. It was so sweet to hear Nikki in there talk the way she talked about you all.

She's so sweet. And just how you gave her license and permission and even inspiration to pursue this thing that might have seemed a little crazy to some parents. Yeah, we just believed in her. We believed in her because she was like, this is what I wanted, well, you know, it was an escape. When she decided to go away to college and she called back when she was having troubles, it was like, oh, thank God, we got something. And it was like a relief for all of us. She alluded to it.

She told me one day, she said, Dad's going to take eight years to get good at this. Wow. I was like eight years? Yeah. It's like you're becoming a doctor or surgeon. Right, right. Yeah. You're going to do residency and internship and everything.

But she said she was. She was spot on. Yeah, she said she never had any doubts if this was it for her, even through the hard times. Yeah. Did you all ever have doubts that this wouldn't work out? I knew how hard she worked at stuff, even as a child and making her friends laugh and everything like that. And so we're like, this is a perfect thing for her. It's going to work.

I had full faith in her. We really didn't have doubts. No, we didn't have down. She was in high school, though. She was in a National Honor Society. She used to like, if she had a paper, she'd stay up until 4 in the morning doing a paper. I used to say, just get a demerit every once in a while. Let it, you know, let it go.

She's a worker. She was just, yeah. And she was a good girl. Yeah. That's apropos here. But she really was. One thing that I think about one teacher, she had a teacher that was a theater guy, Milton Zoth, was his name. And he told her she was in a play August to the T-house moon or T-House of the August moon.

And she had a comedic role. And he told her, he said, you have great comedic timing. Oh, wow. And that was a spark to kind of get her. got her kind of going. Is that amazing? One thing a teacher says can make a big difference in your life. I can't tell how many times I've heard that in interviews.

One teacher, often a teacher says something to inspire them and say, keep going with them. Keep going with that. We believed in her. So what is it like now then to have seen her in the early years? You were talking about going around with her and she's in clubs until 4 a.m. To see her hosting the Golden Globes. It's incredible. I mean, we are so blessed and she's so generous with us.

like she invites us to everything. So we get to run on her coattails. And it's so fun. You're always like, you really want us there? Yeah. Are you sure? Want to make you more nervous? I always think it's going to make her more nervous.

Right. We don't try to talk her out of it or anything. No, exactly. Take the ride. Now, in this particular special, I was just talking with Nikki inside about you all being there in the front row. Right.

And, you know, there's some stuff. I've got a daughter, too, where if she were saying that for me, 10 feet away, I might blush a little bit. How was it for you, Dad? Willie, as I said yesterday, we have to become a newer over the years. But when she first started doing this, we'd go to clubs with our friends. And on the way out, my friends would be like, sorry, dude.

Yeah. Oh, God. And we're like, hey, whatever. So, but, you know, it's propelled her to this level. Her honesty is what always gets me. Yeah. Yeah. I would, could never be that honest in front of a crowd about some dark, deep thoughts.

I know. It sounds like nothing's off limits, huh? Gutsy girl. That's her brand. How's it for you to watch that? I'm Teflon now. I mean, it's like, I really, it's like, huh, she just said that. It's cool.

Whatever. It really is. One of the first jokes Nikki did, though, she was on Last Comic Standing when she first, and she did a show, she said, my mom is a shopaholic. She loves to buy alcohol. Yeah. Got that old joke. Julie couldn't go to the store and buy a bottle.

Couldn't go to the grocery store. She felt bad buying a bottle of a bucket. And I knew everybody at that grocery store. And they're like, oh. Like, yeah, it's not a big problem, obviously. It just seemed like it. Well, you both clearly did a great job. Well, thank you, Willie.

Not just by encouraging her, but she's such a wonderful person, too. Fun to be around. Thank you. Thank you. Yeah. I'm in awe of her. Really. It's easy to be an all of her.

She's a good person. She's a good girl. Good girl with good parents. Oh, thank you, Willie. Thank you so much. Nice to be with you guys. It's so fun. My big thanks again.

to Nikki for a great conversation, and of course, to her parents, Julie and E.J. You can stream Nikki's stand-up special, Good Girl. It's on Hulu now. My thanks to all of you for listening again this week. If you want to hear more of my conversations with our guests every week, be sure to click follow so you never miss an episode. And don't forget to tune in to Sunday today every weekend on NBC to see these interviews with your own two eyes. I'm Willie Geist. We'll see you right back here next week on the Sunday Sit Down podcast. Next.