Inside Conan: An Important Hollywood Podcast - Billy Eichner Revisits His CONAN Remotes and Madonna Obsession

Episode Date: March 29, 2023

Billy Eichner joins Mike and Jessie to discuss crashing the Super Bowl with the CONAN crew, following Madonna all the way to Israel with CONAN producer Frank Smiley, and shooting the classic Grindr remote.Got a question for Inside Conan? Call our voicemail: [phone] or e-mail us at [e-mail].

And now it's time for Inside Conan, an important Hollywood podcast. Hello. Hello. Hi. Hi. Hello, listeners. Welcome back to Inside Conan, an important Hollywood podcast. Welcome back.

And my name's Mike Sweeney, a writer with Conan. I'm Jesse Gaskell, and I'm also a writer with Conan. What a coincidence. We wrote on the Conan show. Some of us wrote on Late Night with Conan O'Brien and The Tonight Show with Conan O'Brien. Yeah. And now we just write emails for him to send to his family. And live in the past, apparently. Yeah, man. Let's talk about what I did 20 years ago.

Well, if you're into that, you're in the right place. Yeah. I think that's the only content that exists now. Yeah, that's right. How are you? I'm good. Yes. Let's see. I have news about a new business in my neighborhood, which I always like to share with you. Should we say the name of the neighborhood? Yeah, it's Highland Park. We're in Los Angeles. Los Angeles. Yes. And I was really excited to tell you about the vegan butcher shop that opened that I thought would be closed by now, but it's thriving. I thought that was, well, you made it sound like it was due to go belly up the second it opened,

but it's thriving. No, there's lines out the door. That's crazy. Of like very soft looking vegans. Is the staff laughing while they serve these people? I don't know. Okay. Yeah. I think, no, I think everyone's into it.

Everyone's taking it seriously. It's serious, yeah. Okay, cool. But I saw a new sign was up just this morning when I was walking my dog, and there's a new eatery in town. Yes. Just a block away from the vegan butcher. Yes. And this one is equally, I mean, this one blows my mind as well.

It shouldn't be successful. It shouldn't be successful. Therefore, it's going to be great. It's extremely specific. And the name of it is Wavy Gravy. Oh. And it is a poutine restaurant. Whoa.

Yeah. Whoa. Poutine, which I kind of think is almost like the neighborhood was having to give equal time. That is. The vegan restaurant had to have its polar opposite move in, which is. That is the exact polar opposite. Same owners. That's the weird part.

This guy's really covering his or her bases. Hedging his bets. Poutine. Everyone knows what poutine is, right? Yeah. Even though I didn't learn until a few years ago. It's like fries covered with gravy and meat. And it's a Canadian national food.

Yes. It just seems so specific to me. Isn't there cheese involved? Oh, yeah. There's definitely. I don't know. I don't know. It's every non-vegan food.

Oh, well, that sounds great. There's beeswax on it. I don't know. So are they going to, maybe the vegan butcher will offer vegan poutine? Vegan poutine. That's what I was thinking. Yeah, yeah, yeah. That they're going to have to compete. Do they add like animal squealing noises coming from the back of the store just to give it some authenticity? Some realism? Yeah, they should. Oh, this is exciting to hear how the poutine, that does sound. I know. It's just incomprehensible to me. I don't, I can't imagine.

I mean, this neighborhood has, like I said, there's a vegan butcher. There's three like independent stationary stores. Wait, what? There's a lot of dispensaries. And then now there's a poutine shop. But there's nowhere to get a sandwich. You can't just get a sandwich. But you can send an apology card saying, I'm sorry, we don't have a sandwich shop here in Highland Park. Yes, exactly. Three stationary stores.

I like that. Yeah, on the same block. Those are the people writing thank you notes. On the same block. And Billie Eilish lives in your neighborhood, I've learned. That's right. She grew up there or she lives there now? She grew up there and she lived there up until very recently.

Okay. Because I had, did I tell you about how I was seeing, there were patrol cars just two blocks away from my house. Yeah. And every day on my walks, I would see these like four corners of this one intersection. Oh. Each one had an unmarked patrol car. The cops are waiting for the poutine shop to open. Or they love vegan meats.

Yeah. So I thought there was some kind of drug bust happening. Like, oh, they've got to be staking out some major drug house. Right. And then I found out that, no, it's Billie Eilish's house. And her address was revealed in the documentary that she did. And so, you know, now there's crazy people going and just wanting to. Oh, she has all these stalkers trying to.

Yeah, just trying to get in. Wow. And do God knows what. But yeah, so she's got 24-hour security. I think that she ended up having to move because of weirdos coming by her house. But her parents still live there, which is really cool.

Is that weird if you're a fan of someone and you just want to go by? Just want to stop by and... Let them know that you're really, really into them. That you'll die without them. I don't see a problem with that. That you'll die without them. And why not go out together?

Yeah, but when Conan had Billie Eilish on his podcast recently, her parents came in and I was like, oh, yeah, I think I've seen them around the neighborhood. Is that true? Did you recognize them? Her dad has a beard. Yes, I saw him. They're very down to earth. They're cool. It was fun to watch on the monitors because

towards the end, she was just kind of scrunched up in her chair. She was like horizontal. Kicking back. She was horizontal. Totally relaxed, like kind of like oh, this has become a safe space for me. Yeah. And that's when Conan bounced. She was under the covers. Yeah, oh, this has become a safe space for me. Yeah. And that's when Conan bounced. She was under the covers. Yeah, no, it was fun.

And I think she even mentions in the podcast that she moved away recently from her parents' house. So she lived with her parents up until really recently. So you listened to the podcast. I just watched. I just look for a body language. That's how I tell whether a podcast is going well or not. And right now. How's this one going?

You seem very tense. You're always relaxed. Well, hey, yeah, let's talk about our podcast. Enough about Conan's podcast. Oh, please. And we have our own Billy this week. Yes. Billy Eichner is on the show.

Yes. We were very excited to have Billy on because he's been a real friend of the show. He has from way back. Yes. In his early days of have Billy on because he's been a real friend of the show. He has from way back. Yes. In his early days of doing Billy on the Street. And speaking of early days of Billy Eichner, I didn't know that appearing on Conan was one of his first appearances on late night television. Yeah. Yeah, yeah, yeah.

Yeah, I know. I think he was just kind of Billy on the Street was like an internet sensation. Right. And was on TruTV. Yes. I believe. And there might have been one network in between. Oh, yeah. There was another Fuse, maybe.

Yes, Fuse. I forget. So you know it's going to be dicey and explosive. But, yeah, and Billy on the Street, I feel like just when that exploded, it was such a great melding of his energy and the streets of New York. Well, and it was a fun advance of late night comedy, too. Right. Like man on the street comedy. And he was doing it in an even weirder way that no one had ever seen before. Yeah, it was really great.

And, you know, I think we can just talk about Billy and not even have him on with our incredible insights. That's right. Wouldn't you rather just listen to us talk about Billy and not even have him on with our incredible insights. That's right. Wouldn't you rather just listen to us talk about our interview with Billy? Yes, yes, yes. While ordering in some vegan meats. No, but since we're doing this season of Inside Conan is Conan on the Road. So we thought we had to have Billy Eichner on to talk about when he crashed the Super Bowl with the Conan crew.

Yes. Billy Eichner on to talk about when he crashed the Super Bowl with the Conan crew. He and Conan producer Frank Smiley also went all the way to Israel to chase Madonna. And then famously, Conan went on Grindr with Billy Eichner's help in a very funny remote. Yes. So Billy's the perfect fit for this season's theme of Conan on the go because we sent sent Billy on the go Conan on the road Conan on the go Conan on the road I don't know what's it outside Conan a inside outside Hollywood unimportant maybe I Van Nuys podcast I don't know where I work. So here's Billy. Well, so Billy Eichner, welcome to Inside Conan. Thank you. You have appeared on Conan, I read 12 times, which I think is maybe up there with the most that anyone has.

Wow. I can't. Yeah, That sounds right though. I mean, it sounds like a lot, but thinking back, um, it's been over 10 years. Yeah. Conan was the, Conan was the first major talk show to have me on as a guest on the couch. Oh, wow. This was about, this was January 2012. Right. Wow. Which is crazy. I didn't even put that together until right now. Yes.

Let's do this again for the 20th. Oh, God. But yeah, it was 10 years ago. And Billy on the Street had just become a TV show. We were three or four weeks into our first season on a rather obscure cable network. So no one knew that it was on. Except for our booking team. That's right.

Yeah, exactly. It was on TruTV, right? Which technically is... It started on a cable network called Fuse. Yes, and the first three seasons were on Fuse, and then we moved to TruTV for seasons four

and five. You moved up to TruTV. Can you imagine? Can you imagine? You know you're in trouble. They're like, well, you're starting here at true right no or i'm moving up no we were at a smaller place how did they um how did conan because was it literally like your show debuted and they saw it and were like oh we've got to get you on or had they already were you already on their radar from your stuff clips that have been on youtube i would imagine yeah i'd had some viral billy on the street videos on youtube before

it became a tv series and they would go very viral on twitter and andy richter the wonderful andy richter was an early billy on the street um And I think that's how I got onto the team Coco Radar initially. And I have a vivid memory because I was very hands-on with the editing of all Billy on the Street things. We have wonderful editors, but I would work with them side by side.

And we were in post-production on one of our first season episodes. I remember this so clearly at a post-production house here in LA. And I remember getting the email from the show's publicist saying that they booked me on Conan, and I could not believe it. I was so excited. Oh, that's great. I love that you remember where you were. That's awesome. Yes. I should give Andy Cohen a shout out because technically I was on his show a week

before, but that's like a different, it's a different type of thing. And I love Andy's show and I've done it a million times, but I grew up with Conan and, you know, that was a real sort of old school, legit late night talk show with the desk and the couch and the monologue and all that. Also, did Andy Cohen call you to do a 10th anniversary?

No. No, he didn't. No, he didn't. He called to do the ball drop at Times Square. Just sneak him some booze. They're like, we need yet another day. We need a triumvirate. CNN requires it.

So anyway, but yeah, it was such a huge moment for me to do Conan. And that was amazing. And we want to talk about when you first went on there. But you just said something that really interested me. I love that you were very hands-on in the editing of Billy on the Street. Because it does, like the way you cut from one thing to the other is so, to me, specific. And I think specific to you. Yeah, it has so much adrenaline. It feels like Billy is editing it. It does feel like you're editing it on the street as you're going. So I love that you kind of had the final say about how that would go out.

The editing is so... There had been a handful of times over the years leading up to the TV show Billy on the Street when TV producers working on some late night show or some pilot would call me and say, hey, we want to do a Billy on the Street video for our show. And they wouldn't let me edit it because they had their own editors. And who was I at the time? I was no one and just happy to get a gig and try to get on TV. So I would let other... I would go and shoot it and I would let other people edit it and then I'd sit and watch what they made and I would just kick my yeah yeah you know and so when it came to the show I insisted on being a part of the editing because I always had been with any of my videos that had

right gone viral and it just felt like it was just part of the as part of the process as anything else. No, I was going to say, Billy, you mentioned doing Billy on the street with other entities, which you did end up doing for Conan. So after shortly, I think after you appeared as a guest on the couch, you went to the Super Bowl to interview people about the Madonna halftime show. And that was really, really funny. I mean, and then there was a whole Madonna series that you did for Conan. Yeah. But it'd be nice to hear a little of how that, I mean, were you approached by people at Conan to do that?

Yeah. And that remains one of my favorite things I've ever done, going to that Super Bowl segment about Madonna. And what was smart about everyone at Conan is that not only did they ask me to do it, which I was like so flattered and did not see it coming at all, but they let me edit it. That's great. And I think that's why Frank Smiley, who is a longtime Conan producer, he went to the Super Bowl with me. He was a producer on all those segments. We ended up going to Israel together, me and Frank Smiley, to cover the opening night of the Madonna tour in Tel Aviv.

I think Frank was just figuring out ways to go to things he wanted to do. Like cool places. I want to go to the Whaley Wall. I want to go to the halftime show. Yes. You haven't lived until you've been with me and Frank Smiley and an all-Israeli crew in Jerusalem. He said it was a mostly female crew in Jerusalem. Interesting.

Yes, that's right. They were fantastic. Yeah. And then when we shot in New York, the final of the Madonna trilogy videos were in New York at Yankee Stadium and it's me and Madonna. Yeah. You met her. Unbelievable. On stage at Yankee Stadium. And for

that, Team Coco and Frank let me use my New York Billy on the Street crew to shoot it. Cool. Because I said, you know, they really know how to do this better than anyone. And so that was very cool. But for the Super Bowl, that was really incredible. I had done Conan as a guest once and I sort of came on and people didn't really know who I was. And I was ranting and raving and crazy. And people either thought it was like the funniest thing or the craziest thing. And a few days later, I got a call saying, hey, do you want to go do a Billy on the Street style video for us at the Super Bowl? It's in Indianapolis this year.

And this was 2012, 10 years ago, and they said, we have crazy access to the Super Bowl. It's like, they give us amazing press passes. We can literally get onto the field. I'm kind of stunned that we had that access.

They were lying. They were just trying to get us to go, okay, I'll go. They're like, we'll scalp tickets once we're there. No, but were lying. Yeah. They were just trying to get him to say, let's go. Okay, I'll go. Yeah, they're like, we'll scalp tickets once we're there. No, but they did. We were on the field. It was wild.

I don't know how they did that. They even got me. I mean, there was a lot that was cut out of the video. I went to all the press conferences. I went to, they have that stupid, like a Super Bowl weekend.

They have like the celebrity bowl where they get like all kinds of random celebrities to play football with, with some former NFL players. So this was cut out of the video. I can't remember why I, maybe it just didn't read or something, but I went to that celebrity bowl like the day before the Superbowl. And I, I didn't play play because i they asked me to play and i was like absolutely um but i said also also calling me a celebrity even now but especially i love that you corrected the non-bad guys please not yet but i i didn't do that but i did i wrote i watched it and we had a crew there and Peyton Manning played in the game.

A very serious man who I obviously didn't know. And again, no one knew me at the time, which was actually great. Yeah, because I could just pretend I was a real sports journalist and then get in there and start asking them whatever crazy pop culture stuff. I think I asked Peyton Manning, have you ever had gay sex? I'm not sure. I honestly, I think that I did. I wish we could talk to Frank and get there. We will talk to Frank. And find out what he answered.

That's what I want to know. He, I went up to Peyton Manning. I asked him, it was essentially what I did the next day at the Super Bowl, which was, how was the game? Any thoughts? Any predictions? Are you excited about Madonna?

And then I think I asked him, okay, maybe this is just in my head. Maybe you drift. Some weird homoerotic fantasy. Yes. But I think I asked Peyton Manning if he's ever had this. God. I was really. And then he said, not yet.

Any suggestions? I don't think for any of it he said a had. God. I was really And then he said, not yet. He, I don't think for any of it he said a word to me. He was stone-faced and did not say anything, which is probably why we didn't use him. He was waiting for SNL.

Exactly. He was waiting for someone bigger. Yeah. He's like, where's Dane Cook? Get me Dane Cook. How this

impact all my endorsements. and so and look i don't blame him um so yeah so uh frank said you want to go to the super bowl it's in indianapolis we have crazy access and of course you know at the time i i had just done conan for the first time my show had just premiered but no one really knew it was there. And I was working so hard on it. And I thought, oh, my God, Conan, the Super Bowl, this is the biggest thing ever. I have to say yes to this. And I said yes and pretended like, oh, yeah, this is a great idea. What a natural fit for me, knowing that I know nothing about football. And I mean, of course, I watch the Super Bowl like everyone, but I watch it as like a cultural event to tweet about, not as a sports fan.

And I so I got off the phone with Frank and I thought, oh, shit, what the fuck am I going to do at the Super Bowl? Like, this is all like a lot of straight dudes, like really intense sports fans from all over the country. What am I going to ask them? You know, this is the opposite of what I do. And then I was like, huh, I wonder who the halftime show is this year, because that's the most pop culture oriented part of the Super Bowl. And thank God it was Madonna. And I am a massive, obsess madonna fan since i was a kid um yeah i read madonna was your bar mitzvah theme or it wasn't exact people like to say that it

wasn't exactly that but she did factor into my bar mitzvah pop music yeah okay was the theme of my bar mitzvah but madonna was my number one and there was a a kind of life-size spray painted airbrush spray painted portrait of her in the cone bra and everything like in a garter belt and cone bra i was you know it's like a birthday party for a 12 year old boy turning into a 13 year old i hope you still have that i know i want you to turn the camera around and it's there in your living room i don't yes i don't have it here um it's part of my paid manning fantasy now it's paid manning in the in the cone bra i i do yes exactly which these days yes would be great for him and for everyone. But I have I don't have the full Madonna, but I have the head and I have one of the hands. It's like it's made out of like what they used to call like. Oh, right, right, right.

Right. But it's it's spray painted and has glitter on it. I mean, by the way, I was ahead of my time. This is 1991. OK, so gay kids were not coming out of the closet at 12 years old. So, you know, this was very progressive for my parents and for everyone involved. Anyway, I'm a massive Madonna fan. So when I saw that Madonna was the halftime show, I thought, okay, that's my in. I'm going to run around asking all of these intense Super Bowl fans

only about Madonna. Like, not going to even touch the game at all. Now, that kind of evolved to, oh, I'll start with asking about the game and then transition into asking about Madonna, and that's where I'll get really passionate and worked up about it. And I pitched that to Frank. He loved it. It made a lot of sense for me. Yeah. I mean, that's the I'll get really passionate and worked up about it. And I pitched that to Frank. He loved it. It made a lot of sense for me. Yeah. I mean, that's the whole remote and it's so perfect.

And it was so perfect. And it was crazy. We were in Super Bowl Village for three days and it's in Indianapolis, which is, you know, a major city, but it's not New York City like I'm used to. So I was a little worried, like, oh, will there be enough people? And what will the energy be like? Because I really feed off of that. But Super Bowl Village, no matter where the game is, they basically turn it into New York City. I mean, it's crazy.

There are so many people and everyone's so excited to be there. And were people good being on camera? Like they came and were comfortable with the cameras being there and yeah well i would i would i for for a lot of them i would ease them into it like i'd be like hey guys like hey bro you excited about the big game and they'd be like yeah yeah yeah and then i'd be like you excited about madonna and then like you know a lot of them would get mad at me one guy one guy i remember called her was like, she's an old hag. And I was like, you're old.

And I was like, get mad at him. I know. I kind of was shocked that somebody would call Madonna an old hag. I was like, how dare you? By the way, this was 10 years ago. And then we did end up having crazy access where on the day of the Super Bowl, me and Frank and Jason Chalemi was the producer. Yeah. Jason. Yeah. Rowe was there behind the A-cam, which is the camera I'm mostly talking to. And I remember, so we're on the field. And for the first quarter, I was like, this is insane

because it's the Super Bowl. I've never been to an NFL game. And now I'm on the field at the Super Bowl with all of these journalists. And it's like the biggest entertainment event of the year. And I remember thinking, oh, it was lit for TV, the game. It was lit for entertainment. It was lit for entertainment. It was lit for a TV show. It wasn't really lit for the people watching in the stands,

because of course not, because it's the billion people at home who are watching. So everything is produced for TV. And that was an interesting moment because I always thought like, oh, this is like the ultimate sporting event, which it is,

but it's really pop culture also. This is entertainment. This is lit for entertainment. It's like Vegas. You know, it was that. Everyone's had hair and makeup, even the players. Exactly. I remember I went up to the cheerleaders and asked them if they had any clothes.

But you're right. The vibe there is the teams are almost secondary. Honestly, it felt like dancing with the stars on steroids in helmets. Really, that's what it comes out at the end. Yes, exactly. It felt like a pageant. It felt like a pageant. It wasn't that different than when I go see the Radio City Christmas Spectacular. Like really, it was, I found, I found that to be fascinating. And then, but I kind of had to, you know, I had to stay in character. I couldn't get overwhelmed by being at the Super Bowl. Like I had to sort of stay focused on being Billy on the street who doesn't really give a fuck

about the Super Bowl and is just there to see madonna and it was so cool because for the madonna halftime show we were literally on the 50 yard line and that was a real challenge because i'm a real madonna fan i mean i've seen so part of me was like holy shit i gotta get in the mosh pit madonna halftime show and i want to watch it as a fan but the camera's on me waiting for me to comment as Billy on the street. And I was like, Oh shit, I can't like fully enjoy. This is a fan.

I'm here to work. You wanted to take your shirt off and get in the, in the mosh pit. Yeah. That was the spirit underneath. Take the shirt off, get camera makeup on your chest and then run into the mosh pit. Exactly.

And I remember thinking yeah they announced her they were like ladies and gentlemen Madonna and like I'm like freaking out both genuinely and performatively it's nice when those two correlate it's very rare but

yes and I'm freaking out but I was clearly way more excited than a lot of other people there. Including Madonna. It wasn't. Yeah. It wasn't a Madonna crowd, obviously. Though I think her halftime show ended up being the most watched one of all time.

It's one of the ones I remember the most of every halftime show. It was a true spectacle and it was great. It was really fun. And Nicki Minaj was there and CeeLo, shit, all these guests. And that was fun. And then at the end of the game, the Giants win. That was also a crazy thing for me because even though I'm not the biggest NFL fan in the world, the Giants are my home team. I'm a New Yorker.

You know, when I did care about football a little bit and watch football with my dad when I was younger, we cared about the Giants. Right. So it was wild that of all years, it was like Madonna and the Giants and they won. And I was like literally like standing right near the end zone when the Giants scored a they won. And I was literally standing right near the end zone when the Giants scored a touchdown. It was really wild. And then at the end of the game, the Giants win. And I'm standing off sides and just looking at the camera and being like, oh my God, the Giants won.

Madonna was amazing. And everyone's freaking out about the Giants and there's confetti and people are crying and fireworks. And I'm screaming about Madonna into the camera. And all of a sudden people start, you know, walking onto the field, family members of the, you know, everyone who works for the teams are running onto the field.

Other journalists with cameras and, you know, NBC News and all the, you know, everyone who works for the teams are running onto the field, other journalists with cameras and, you know, NBC news and all the, you know, it's this freaking Superbowl. Right. And I knew in my head that I needed to just go for it and work up the guts. I was like, you literally can run across the Superbow field right now screaming about Madonna. And in my mind, I was like, you have to do it. But I was scared. I was wondering whether you were getting nervous with something like that. I knew it. I knew for comedic purposes it needed to happen, that I would never get this chance again.

It was Madonna, like my number one, like it just needed to happen, but it was scary. And then I start kind of running onto the field slowly and Rowe, like who's behind the camera, but he kind of like looks at me and he gives me a nod, right? And I remember this so vividly

and he's like basically telling me, he was like, go for it. Yeah. Do your thing. You know, and that's and I was so to this day, to this day, like so appreciative of that. Like I needed that little kind of pep talk in a way. And then I like took off and like ran right to center field, like in the middle of where all players are and all the nfl execs and it's confetti and i'm screaming like and i'm like madonna was amazing and you ran up to two players and you're like what'd you think of madonna and they had just won they just finished the game oh Oh, my God. So great. These two New York Giants who had just won the game.

They're like these huge dudes. It's like massive athletes who just won the Super Bowl. These grown men are crying. And their wives are there and their kids and all these people. And I ran up to them and I was like, hey, man, great game. Congratulations. And one of them spoke to me like very genuinely and was like, yeah, we played really hard. And like, you know know halftime we like

we like you know we recalibrated and blah blah blah and I was like did you see Madonna? He just looked at me like what? He was like no I was in the locker room No we don't watch it He felt a little sheepish about it like uh

I was supposed to watch it I did that with a couple of the players and to this day that i don't even for me i don't know where that's so ballsy well also i i know frank smiley absolutely was probably like you gotta run across that field yeah because he loves he loves being transgressive it was amazing and, you know, I certainly wasn't looking to, like, disrespect the players in any way. But but there was part of me that was like, you know, I'm certainly the biggest Madonna fan at the Super Bowl right now. Like, these are all jocks. Right.

Sports fans. box sports fans and i am going to be the voice of like you know gay madonna fans and make make her the priority which especially for i don't know how sort of transgressive or progressive it would seem right now it's still probably seem a little shocking but things were very different 10 years ago yeah than they are right now in many ways and um especially in terms of like gay comedians and a gay sensibility being able to sort of be front and center um like that um especially on a show like conan it's not for a gay network it's not it's not andy cohen right it's a more mainstream thing just for smart comedy fans. So I was glad that I

did that. It was such a simple, great comedy idea to be the one person. And then the way it was just you running across that field because you're so used to seeing that after every Super Bowl and now it's you doing it

and it's all about the halftime show. It's just, it's, I think that's why it's so crazily memorable. Yeah, it's so joyful too. Oh, and Frank said, he gave a fun detail. He said, you know, you had a handler, I guess, a Super Bowl handler. And he said that the guy was like, you know, you could stand in the end zone when the game's over,

but you can't run out on the field. That's the one rule. And then you guys just took off. Yeah. I was like, bye. I don't remember that. I don't even remember that. Maybe that actually explains why, another reason why I was nervous. Yes, of course.

And then he's eyes like well did you ever did you get shit about it afterwards he said now like you know i i it's all who was even keeping track once the game's over and there's 300 other people trying to shoot comedy remotes on the field i did i did go up to um this didn't make it in because he clearly wasn't having it but spike lee of course was on the field okay when the giants won and so of course i see spike lee and of course i mean he's a genius i have a lot of respect for spike lee of course but i was like billy on the street's not gonna be afraid of spike lee so i went right up to Spike Lee. And I actually, from what I remember, like Madonna's work with Spike Lee. I know everything about Madonna, like obscure things.

She had like a cameo in his movie Girl 6. So I was like, I bet Spike Lee. They're like hugely famous people, but also like kind of legit New York artists and all of that. And so I thought Spike Lee must like Madonna, like in my head. So when I was going up to the players, I saw Spike Lee. So I go up to Spike Lee and I'm like, I'm like, Spike Lee, Spike Lee,

what'd you think of Madonna? Wasn't Madonna amazing? Thinking he would probably even understand that I'm joking, you know? Because he's a great filmmaker. And he looked at me and he was so angry. And he just looked at me and said, the Giants just won the Super Bowl. What the fuck are you asking me about Madonna for?

Okay. And that spiked Lee. I was like, oh, shit. Okay. And that, I got a little scared. I got with the more cuddly players. Yeah. The players were just having such a joyful moment.

They didn't, I didn't, I didn't really phase them. I love you said like, well, Billy on the streets would have no problem running up to Spike Lee. Like, I love that he's kind of a persona. He's alter ego. Like, there's a difference for you between the character and Billy Eichner. Definitely. But then the hardest thing, the biggest example of that was when, so then we go to Israel because the Super Bowl video, people really liked that video. And this was just a few months later.

Yeah, you guys called again and said, what if we... Frank wants to take another trip. Yeah, exactly. Basically that. Right. Frank doesn't want to work. So Frank's like, Madonna's opening her tour in Israel, in Tel Aviv. Should we go to Israel?

And I said, are you insane? I said, we're going to go to Israel. I'm a Jew, but I've never been to Israel. Oh, wow. But I said, what're going to go to Israel. I'm a Jew, but I've never been to Israel. But I said, what? Are you kidding? We're going to go to Israel for a two minute comedy bit. Those were the days, let me tell you.

And so and we did. And at that point, what happened was Madonna's whole team, manager, publicist, everyone, they had all seen the Super Bowl video and Madonna was out promoting her new album at the time and so they oh that's right oh great right they loved it and they all reached out to me telling me how much they loved it and that I'm Madonna had seen it and from that moment on, her publicist said, like, before the end of the year, I am getting you in a video with Madonna. She literally said, like, over my dead body,

will Madonna not be in a video? That's unbelievable. Classic publicist. I follow Madonna like a hawk for decades. She doesn't do those things. Yeah. Like, it's very rare but Madonna does have a really good sense of humor and she likes a particular type of comedy so it

made sense Madonna was one of the first famous Americans to talk about Sasha Baron Cohen and if you remember Sasha plays Ali G in Madonna's music video. That's before Americans really knew who he was. Wow. Before he had his Ali G show on HBO here. And she'd been living in the UK, of course. And so she was familiar and she was a very early adopter of Ricky Gervais. So she likes a certain type of. She was taking UCB classes.

Exactly. She's a real underground comedy hipster. Yeah. is she's a real underground comedy hipster yeah so like I guess when you think about it that way it kind of made sense that she would find my style amusing yeah and it's also so positive I mean it's you love her so much then that's obvious oh yeah you know if if you're her you're like well this is just heartwarming it was coming from a very real place. It was just sort of heightened to Billy on the street mode. But so then we go to Israel, but it's the opening night of her tour. She's nervous.

And understandably, she was like, I can't do some comedy bit right now. So I end up talking to her dancers and other fans and stuff. And that was fine. And then when she, her tour got to Yankee Stadium in New York, her publicist said, OK, like, you know, now she's been touring for a few months. She's ready to do a thing with you. And so basically they said, you know, show up at Yankee Stadium with your crew. We'll get you backstage passes when she's rehearsing during the day on stage and she doesn't want to script it out and i said that to them i said we cannot script it out the whole thing will die if it isn't its normal spontaneous thing

and a lot of celebrities especially if you're not a comedy person you're scared of that you don't want to improvise right and so they they said that they understood that madonna understood and she said they told me there's two points during the rehearsal um after this song and after this other song at the end when you can run on with your crew and do your thing with her and she's gonna know that you're coming but she won't know what you're gonna say and she will just respond accordingly and so we did that and it was truly the most surreal thing ever for me also billy on the street had only been on a year at this point i wasn't used to dealing with celebrities like this and even if i had been madonna would have always been like the number one, can we get her type of person.

So the fact that it was happening so early, it just was also strange. And then I'm face to face with Madonna. And genuinely starstruck, I'm sure. Right. sure like right that's that was the biggest example ever of you have to somehow forget that you're starstruck because billy on the street would still yell yeah yeah that you can't all of a sudden sort of cower on the street is a sociopath so he doesn't get nervous but i think everyone needs some i was like it's gonna in their yeah blood system yeah i i was like you know if you cower and just sort of fan girl out on her a i know madonna enough to know that she's gonna think that's lame yeah and b i was like the whole i was like the the only thing that's gonna make this funny is if you continue to do your thing, that even Madonna isn't good enough.

Yeah. And that you're angry. Find a reason to be angry at her, too. Right. Because she didn't do Vogue. Yeah. Right. And so I ask her if she's going to perform Vogue that night when she said she yells at me, no, and she's not going to do Holiday.

And I get really angry. Start screaming at her. Anyway. It was totally wild. So you actually met Madonna. Have you encountered her any time since then? Well, the other thing, for people who are interested in such things, so her publicist at the time, who has since retired,

but her publicist who was her publicist for decades, going back to like 80s, like a virgin, like a prayer, like, you know, her name was Liz Rosenberg, a legendary publicist who also represented Cher and Stevie Nicks and, you know, all these icons, right? She was a character unto herself, Liz Rosenberg. I know so much about Madonna that I was almost more starstruck meeting Liz Rosenberg because I know so much about Madonna that I was almost more starstruck meeting Liz

Rosenberg because I've been reading about her so many years. And I have other friends of mine, other gay friends of mine from my generation who also are obsessed with Madonna fans. And I remember like getting emails from Liz Rosenberg and being like, guys, I just got an email from Liz Rosenberg. And like all of us just like freaking out. It was the best.

Rosenbergers, that's what you call Rosenberg fans. I'm a Liz Rosenberg fan girl. I am. And so what I had said to Liz was Liz said, I want she was like, you know, you'll do the screaming thing and you'll scream at her or whatever you're going to do. They didn't ask me, you know, they didn't tell me what to do. They knew vaguely what I was going to do. And then she said, I really want to get you in a one-on-one interview with her after the shouting part. Yeah.

And I said, oh, okay. And while we were shooting it, we did like the two bits where I kind of ambush her on stage and then and then Liz was waiting around to see if Madonna would be up for the interview the one-on-one and it looked like she wasn't going to and I was a little disappointed and then she and then I looked at Liz. I was like, Liz, we got to make this happen. And and and she did. And Madonna came like after she was done rehearsing the show. And we do like a one on one interview. And for all like the celebrities I've met and all the cool things I've gotten to do, this is still one of the highlights of my life.

Because Madonna is a really cool customer, you know, and she doesn't like to break. Yeah. Right. And she always wants to seem like she's in control, you know, and that's just part of her. Like I'm a strong woman persona, which of course I love, but, um, I know underneath it, she has a sense of humor. Otherwise she wouldn't let me even do this. Right. And so, so I'm talking to her and it's a pretty kind of cut dry interview about her tour. And I'm like, I followed you all over. I went to the super bowl. I went to Israel and now I'm here and all these things. And I told her that in Israel, I went to the wailing wall.

And I told her that, cause you know, when people go to the wailing wall, they write down a little you know when people go to the wailing wall they write down a little prayer right to god and they stick it in the wall and i said i told her i said i wrote a little prayer to god and she said what did you write and i said that you would sing both on your tour and she cracked up oh man she couldn't like yeah she couldn't keep a straight face as hard as she was trying to sort of not indulge me. And I got her and that to this day is like one of the things I am most

proud of. I would have stopped the interview and walked away. It was amazing. And I have a screen grab of the moment that she laughs and it's like I literally have it framed. It's one of And I have a screen grab of the moment that she laughs. And it's like, I literally have it framed.

It's one of my favorite things. Well, so we'd be remiss if we did not talk about your remote where you led Conan through Grindr. Oh, yeah. Which was really fun. I was there for that one, actually. I don't know if you remember me being there, but it was so fun. Also one of my favorite

things I've ever done. Yeah, truly. It was so, so funny, because we had done a remote where he went on Tinder with Dave Franco. And then it was kind of like, I don't even remember how the idea came up for him to go on Grindr with you, Billy, but it was kind of like, I don't even remember how the idea came up for him to go on Grindr with you, Billy,

but it was sort of just always assumed he was going to do it in a way. Like, I think it was such an obvious idea that everyone was just like, yeah, well, that's eventually. So I remember it being on the board, but it was like Grindr with Billy Eichner. Like, we were thinking about that. That's so funny. So I was, yeah, everyone in my world thought i came up with the idea because it's grinder right so gay focused and you know again like the madonna clip although the grinder one even more when was the grinder 2014 20 2015 okay so numerically, that doesn't seem like that long ago.

But culturally, in terms of LGBTQ stuff, especially in mainstream pop culture, that is a world away from where we are now. I mean, there has been such an evolution. So everyone thought that was my idea. And I said, no, Conan's team came to me with the idea. Yeah, no, I mean, I don't know if Conan knew about Grindr, but we did introduce him to it. Yeah. And it was fantastic because in those days, I mean, even now you don't see a ton of crossover necessarily.

There's a lot more visibility for like gay comedians and LGBTQ comedy and all of that. But you don't see as much crossover between the straight comedy world and the gay comedy world. Like sometimes those are kept very separate unless we have, we're sort of a member of an ensemble on a sitcom or something. But that was what was so amazing.

It was like the coming of together of two worlds. And I always thought Conan was always so progressive in that way. And I always was really grateful for that because with Conan it was never about sexual orientation or anything. It was about comedy. That's all

it was about. Like, is this worth doing for comedic purposes? And that's part of the reason I love that Grindr bit so much. Yeah, and I think for Conan, even, it's like Tinder is as alien to him as Grindr is just because he's so far from being on a dating app in his current life.

So I think that it was sort of just, like you said, it wasn't, it was kind of sexually neutral, but he was just like an alien in this land. You know what else I think it was? Yes. On Tinder. It was so great.

It was kind of slow going, getting women interested in him. And I think part of the joke was, you know, he got a reply finally from a woman, but she was 74 and even she kind of ended up blowing him off.

So I think he genuinely was excited that things were happening faster on Grindr. Yeah, it was a lot more action on Grindr. You know, some people were ready to get it on with him. I think who doesn't get excited about that, regardless of gender. Oh, it was so fun. And we put we put photos of him on grinder nothing x-rated but i do think he took his shirt off um and then we did

meet a man for him and then reveal and the guy didn't believe that it was real obviously because he recognized conan i remember behind the scenes because we wanted to go meet up with the guy that night. Yeah. You know, so I had to get on the phone with the guy and explain that this was real, that I was gay, that, you know,

I put Conan on Grindr, that we were going to come together as a team to meet him and that it wasn't sketchy and we weren't trying to, like, catfish him or anything. But, yeah. Right, because there's multiple layers

of, like, but we also need you to be on him or anything. Right, because there's multiple layers of like, but we also need you to be on camera. So you have to agree to sign our consent form. Yes, right, exactly. Yeah, exactly. And I had had a lot of experience with that visibility on the street. And no pressure.

Just if you don't do this, we don't have an ending to this piece. Exactly. Right. I said that. I was like, no one's having sex here. Conan's not gay, but we would just like to come meet you and talk to you.

And we did. We met him in the parking lot of a Bond's in Burbank. We probably weren't the only Grindr meetup happening there. Who knows? No. And Conan and I, you guys had this van that you rented for Conan and I to drive to meet the guy, and Conan and I, you guys had this van that you rented for Conan and I to drive to meet the guy.

And you had spray painted like portraits of Liza Minnelli and Cher and other gay icons like on the outside. That van already existed. And Conan and I really did. Oh, yeah. That was just his personal van. Yeah, exactly. Yet I love that the guy you met up with, like, you're like, who's who's on personal van. Yeah, exactly. Yet, I love the guy you met up with. You're like, who's on the van?

He goes, well, that's Cher. But he didn't know Liza Minnelli. He didn't know Liza. And then he goes, oh my God, I forgot about that. He was young. Yeah. He said, I'm not talking. Which was hilarious.

He was young. That's why. It was a gender equality, for sure. I forgot that you gave him a heads up but he still seemed shocked that like there's a TV camera there I feel like when you first meet up with him oh yeah and shocked

that it was actually Conan well I wouldn't believe someone if they were on a dating app saying it was a celebrity and they wanted to come meet of course I wouldn't believe that it they were on a dating app saying it was a celebrity and they wanted to come meet. Of course, I wouldn't believe that it was really Ben Affleck, for instance. Right. And we literally met him on Grindr. Like, it wasn't set up in advance.

Grindr wasn't involved. Like, corporate Grindr didn't know. We just, it was very organic and real. We went on Grindr. We made an account. We put up photos of Conan. I always love commenters who are like, oh, the whole thing's scripted. It's on Grindr. We made an account. We put up photos of Conan. I always love commenters who are like, oh, the whole thing's scripted.

It's like, ugh. No, we would have scripted it better if we had scripted it. All right. Well, thank you, Billy Eichner, for joining us. Thank you, Billy. He's so funny. Yeah, he's great. Hey, guess what?

We're back with listener questions. Oh, Billy. He's so funny. Yeah, he's great. Hey, guess what? We're back with listener questions. Oh, man. I miss these. It's the only reason we actually do this podcast. It is. Is for all those

listener questions. Otherwise, I don't get any emails. Plus, once in a while, they compliment us. I know. And I need it because no one else

in my life ever. I have to get it from strangers because anyone who knows me is like, yeah, sure. Yeah. I think it matters more from strangers, too who knows me is like, yeah, sure. Yeah. I think it matters more from strangers. Oh, always.

They don't know how much I need. The more superficial, the better with me. It feels objective. Anyway, here's a question. Dear Inside Conan podcast, I think everyone is familiar with the bit regarding Jordan on his role on Team Coco. But I'm curious, what does Jeff Ross, the executive producer, do on the show? Thanks. Moshi Moshi from Tokyo.

Three question marks after that question. So Toshi, or I mean Moshi, Moshi Moshi, really wants to know. Yeah, and honestly, so do I. Yeah. So we're calling in the big guns to get to the bottom of this. Yeah. We didn't feel capable of answering this question on our own. The big gun.

Yeah. David Hopping. David Hopping is assistant to Jeff Ross and Conan O'Brien. Yes. So next time we'll ask you what Conan does. Yes. Great. But for right now, we're going to start with what Jeff Ross does. Yes. But for right now, everybody needs to know. We're going to start

with what Jeff Ross does. Okay. I feel like anytime someone asks me what Jeff does, I just say he does it all. He does it all. There you go, Moshi.

I say he does it all. I feel like any final decision is made by Jeff, right? Uh-huh. I mean, Conan always does the bit that he has a lot of dinner reservations, which I can confirm. Do you make those reservations? I do.

And they always know exactly who he is when I call. It's great. Because it's only two restaurants. Right. He knows how to do it. They treat me well. You know, they know me. It's pretty good.

Do you ever make a reservation for Jeff Ross and then you take the reservation? No, but you know what? Ever since I started assisting both of them, my like open table and my Resi account is all confused. Like Conan showed up at a restaurant once. They didn't have it. And then he called me. He was like, you made it under Jeff Ross. So now he knows just to go as Jeff Ross.

So I always just say, you know what? If it's not Conan, it's Jeff. Was he like, they gave me a better table as Jeff. Can you imagine? They were like, right this way, Mr. Ross. Yes. VIP section. This Jeff Ross looks like that guy, Conan O'Brien.

I will say my favorite thing is whenever I would get emails meant for the comedian, Jeff Ross. Jeff Ross. Yeah. And what kind of emails would those be? Like, I remember once it was like some booking email and I was like, Jeffrey, you doing a comedy show? Yeah. You know, I'll rake them over the coals. He's just trying something new.

I wonder if Jeff Ross, the comedian, is getting, you know, reservations. Yeah. Right. So three guys are showing up at restaurants. Spago. This is very confusing. And what's the comedian Jeff Ross do? Do you know that?

What does he do? He does comedy. There you go. Okay. You've got an answer for everything. You know, you just keep it vague. Yeah. So Jeff is kind of like the buck stops here guy.

Right. Yeah. He's got the final stops here guy. Right. Yeah. He's got the final word on every business decision. Everything, yeah. Like, you know, if you want a raise, go talk to Jeff. Right. I didn't know that. Should we call it then now?

That explains a lot. I need to book some time with Jeff. Yes. I got his calendar right here. I've been talking to Jordan Schlansky about my raises for years and nothing's ever happened. For years? That's been a mistake. Well, you have to manage their calendars.

I do. Which seems difficult. I've only messed up one time and I put one of Conan's podcast recordings in Jeff's calendar. But everything's fine. Everything worked out. That's not a bad thing. Yeah. That's a great But everything's fine. Everything worked out. That's not a bad thing. Yeah. That's a great episode

of Jeff Ross. It seems like he'd want to know when Conan's recording a podcast anyway. Yeah. Now they're just in both. So even when you make

a mistake, you're doing everything right. Yeah. It's unbelievable. I'm really good at my job. You know, we're really actually learning what David Hopping does.

Yeah, that's right. We did not answer the question. Very carefully avoided it. The buck stops here with Jeff. I like that. And I think that helps everyone know, do you know what I mean, that there's a grown-up somewhere in the building. He's up in his... Or at a restaurant.

Either way, he's reachable. Yeah. And yeah. I will say Jeff is the fastest texter if you text him. Oh, really? Responds instantly. I will say. No, I didn't have anything. I'm very impressed by that as well.

And I think that is such a great habit to have. And I envy all those. I feel my, you know, calendaring a text for 10 days from now is also another great way to go. I get a text and like I have to throw my phone across the room. It scares me when a text comes through. Oh, I'm so happy to hear that. Yeah. I am terrified because it's like.

What's this going to be? Somebody wants me to do something. And then people are being funny on a group text. I'm like, fuck. Yeah. Fuck. And I have to go workshop some lines. And what font, you know, should I pick a funnier font? And it's like that throws me.

It's a lot of pressure. And then I go to, I have to take to my bed. But maybe that's the writer's brain. And, you know, if you're an executive, you have an executive producer brain, you just fire it off. Or maybe it's a low self-esteem brain. Maybe that's it. I think that's what it is. I don't think Jeff has low self-esteem.

No. No. He just fires right back. Yeah. But yeah, I don't think he worries about typos or anything. Like I worry about, oh my God, it's a proper, I need to put it in quotes. Or like do I need to add a smiley face so the person knows I'm being fun. Or I'm referencing a title with the word the in the middle.

Oh, that's lowercase, not capital. Like I've got to Google that and double check. Is into also capitalized, you know? Right? Yeah. There's a lot to it. Yeah. Because these texts are going to live on. Right. Especially if it's the last one you sent. During the lawsuit.

Before you died in a car accident. Oh my God. That'll be happening. We both had a different dark fear yours are that your text no but sometimes

I do think about that when texts are read in are subpoenaed and then read in court oh yes

that's terrifying to me no there used to be writers group emails where I'm like I'm not getting into this because yeah you know

it's all everything's coming out eventually even if you delete it everything's coming out eventually. Even if you delete it, it's still there. It's still there. Yeah.

Actually, our lawyers are here to... As your job, David, is there anything that's like off limits for you where you're like, oh, I'm not going to pick up your dry cleaning or would you have to do something like that if you were asked? I pretty much just say yes to it. Yeah, I'm not going to pick up your dry cleaning or would you have to do something like that

if you were asked? I pretty much just say yes to that. I knew the answer to that one. Nice of you to ask, Jesse. But I believe the answer is I'll get it right away. I was wrong.

Do you, what are Conan and Jeff's coffee orders? Conan's is just a black coffee with almond milk on the side. Okay. Jeff usually doesn't do coffee, but for a while he was always getting these like triple shot like espresso drinks. Oh, that's a lot of coffee.

And he would do it before a meeting and it would really get him fired up. Oh. Oh. Sell, sell, sell. This is good to know. Coffee's for closers. But he said he used to. He doesn't now.

He doesn't do it. He hasn't done it in a while yeah he's like I always knew it was gonna be a big day now he's just into water he's got that big

jug of water hydrating yeah they're both drinking water constantly yeah and just peeing constantly so much water

so much liquid I know and almonds water and almonds water and almonds but Jeff Ross diet that is his diet if you wanna get to the top

and have the buck stop with you, almonds and water. Unless you're allergic, then don't do that. Well, that's a great caveat. Thank you, David. If you're allergic to water, don't drink water. I have so many

follow-up questions. Is that an allergy? Probably. People are allergic to everything these days. Wait, what's that, David? He nodded his head when you said a sentence. Yeah. My cousin's girlfriend is allergic to water. To water?

Oh, my God. Wait, that's Sean. It really does sound like a lie. You can drink it, but you can't touch it. What? You get like hives. You have to take a medication. I think she's doing that to get out of family vacations.

Yes. She's doing that to get out of living. I mean, like, what could she do? I can't go outside. What about rain? Yeah, that's what I was going to ask. And because there's also the issue with sweat. She can't, like, work out.

Wait. I am going to ask all this to be cut. She's allergic to her own sweat? Yes, yeah. She can't exercise because the sweat makes her break out in hives. I think I might have this allergy, too. I'm suddenly coming down with an allergy. And who is this?

She's married to your- Yeah, cousin's girlfriend. Your cousin's girlfriend. Oh, this is one of those urban legends. No, I had dinner with her last month. My cousin's girlfriend, she's allergic to water. We've all got a cousin's girlfriend. Oh, air and water, that's the worst one.

Oh, no. She's allergic to hydrogen coupled with oxygen or alone. Well, you know what I'm not allergic to? You, David Hopper. David, we can't get enough. You're delightful. Yes. I think we're going to have you on us all the time with some more.

But we need to dig deeper into. We need more questions about David and and what yeah yeah yeah yeah i'll write some i just want to probe into the darker you must have well we'll get into it well yeah you can send us questions please do we really do love it you do these great segues to sum things up and then i just go off like i'm like a fucking truck that's dumping stuff off the back. You think I'm just doing this at random? Yes, go ahead, Jessie. Please send us your questions. You can email us if you're scared of talking on the phone like we are. Yes. Insideconanpod at gmail.com. Or if you're more of a Jeff Ross type, you can call us. Leave a voicemail at 323-209-1079.

Beautifully done. Thank you. The buck stops with you. Buck stops here. It should. Oh, and if you like the show, you can support us by rating Inside Conan, an important Hollywood podcast on iTunes

and leaving us a review. It seems like a lot of homework we're giving. I'm not pressuring. Do the like a lot of homework we're giving. I'm not pursuing. This is all coming from Jesse. I just, you listening's enough for me. Yes, and send us, do 10 push-ups and... There you go.

Send us... And in return, well, we love you. Yeah, we love you. Inside Conan, an important Hollywood podcast, is hosted by Mike Sweeney and me, Jesse Gaskell. You can rate and review the show on Apple Podcasts. And of course, please subscribe and tell a friend to listen to Inside Conan

on Apple Podcasts, Spotify, Stitcher, Google Podcasts, or whatever platform you like best. It's the Conan Show. Put on your hat. It's the Conan Show. Put on your hat. It's the Conan Show. Try on some spats. You're gonna have a laugh. Give birth to a calf.

It's Conan! This has been a Team Coco production.