Inside Conan: An Important Hollywood Podcast - Frank Smiley & Michael Gordon

Episode Date: December 25, 2020

Merry Christmas! Writer/producer Frank Smiley & writer Michael Gordon (Conan, Late Night with Conan O’Brien) join writers Mike Sweeney and Jessie Gaskell to talk about helping make the Late Night show different from other talk shows in the early days, the time director Abel Ferrara walked out before his interview, the failed rehearsal bit that made Conan hold his head in shame, the process of prepping a guest for a show, the origin of Michael’s character the Masturbating Bear, and Frank playing Mother Teresa trashing her hotel room. Plus, Mike and Jessie answer a listener question about the whereabouts of The Masturbating Bear. Abel Ferrara on Late Night with Conan: https://youtu.be/aY7yyhjOXWw Christmas Shopping Desk Drive on Late Night with Conan: https://youtu.be/Fa6Vj5No7qI Conan Reveals Who Is Playing The Masturbating Bear: https://youtu.be/k4QGFnqnQ90 Got a question for Inside Conan? Call our voicemail: [phone] and e-mail us at [e-mail] For Conan videos, tour dates and more visit TeamCoco.com

And now, it's time for Inside Conan, an important Hollywood podcast. Welcome to Inside Conan, an important Hollywood podcast. Wow, I feel like you've been taking voiceover lessons. I've really been working hard. On a Will Arnett impression. That's right. A Batman. We are your hosts.

I'm Jessie Gaskell, and this is Mike Sweeney, also known as... Sweeney, Mike. And we're writers on The Conan Show. And we have a podcast. I don't know. It must be a write-off for the company. I don't know. They gave us a podcast. I don't know. It must be a write-off for the company. I don't know. They gave us a podcast. I think it's a money laundering flow-through entity. Yes. We've asked them to open the books several times and they said, which set? Anyway.

Anyway. We launder money and we occasionally talk about the Conan show. Yes. We tell stories of Conan's past, present, and future. It's like a Christmas carol. Exactly. Oh, today's show is It's Christmas. It is. It's literally Christmas.

I want people to think we're recording this on Christmas. We've been talking about how Conan is releasing a Christmas album sort of piecemeal. He started uploading them a couple weeks ago, the first song. Was this a lifelong dream of his? I didn't know where this came from. You're assuming there wasn't an incredible groundswell of demand for these recordings. He did, what was the first Christmas song he did? It was Run Run Rudolph.

Oh, good one. Isn't that a Chuck Berry song? Yes. Yeah, yeah, yeah. That Chuck Berry song that sounds so different from all the other Chuck Berry songs. Right. song he did it was uh run run rudolph oh good one isn't that chuck berry yes yeah yeah that chuck berry song that sounds so different from all the other chuck berry songs right i love chuck berry chuck berries uh he was he was a madman there's so many great crazy stories about chuck berry i know one someone told me but i listen now it's not the time yeah so he's saying run run rudolph and uh i think uh people really liked it online and

so now he's gone back to record more christmas songs oh that's great it's scary because there are literally i realize hundreds of christmas songs so this could oh yeah yeah he claims at the beginning of each one it's for charity i think we should call this charity see if it even exists the charity is Conan's ego. Yeah, exactly. It's another front. Well, speaking of songs, I also saw that he released a version of him playing the Georgia Satellites' Keep Your Hands to Yourself, which he used to play for us as punishment in rehearsals. Yeah, I think he even says that in the intro to the song, explains that if we're in rehearsal and a comedy bit wasn't ready to go,

sometimes he'd even count down like, three, two, one. And then you'd be like, no! I got some change in my pocket. But I don't hate that song. I mean, I like the song. I always liked that song, too. If it was your sketch that was delayed, I would find it to be a relief because

it would eat up. It was better than everyone sitting around looking really tense and silent. Yeah, because no one can laugh when they're in that mode. Right. But then he kind of warms them up for you. Yes, it kind of helps break the tension. So that's another reason I don't think I did that song. It used to be sometimes he'd play it while you were trying to talk to the stage managers and stuff. And then it's just like, all right, come on. Yeah. Now you're sabotaging things. Right. You'd be screaming like, we're going to rehearse

it again. The whole band would back him. So it was deafening. I know. Well, we have a great show today with a couple of OG Conan staffers. Yes. We have two guests today. Two guests. That's always fun. And they're not married to each other. No. Our two guests both started with the show when it originated in September of 93. So lately, we talked to to Jeff Ross and he had some great origin story stories about how the show began. And we're going to continue that today with our guests, writer, Michael Gordon and writer, producer, Frank Smiley. Michael Gordon and Frank Smiley. Hello. Hello.

Hello. I can't believe we've got both of you together. I know. How did you do it? I don't know. They've been notoriously feuding for years. That. Hello. I can't believe we've got both of you together. I know. How did you do it? I don't know. We've been notoriously feuding for years. That's right. We're going to hash it out now on the show.

No, but we thought it would be fun to talk to two people who were there at the beginning of the show, late night with Conan O'Brien back in 1993. You know, both of you have had such a long run and experience with the show. You know, we just thought it would be great to chat with you guys well let's find out okay did you two meet for the first time when the show was getting underway back in 1993 when i uh got to new york i didn't know anybody on the show at all. You came from L.A.? Yeah, from L.A. I met Conan once at a Johnny Rockets near the Beverly Center.

I know that Johnny Rockets. That's where he does all his job interviews. It was a great chat. But other than that, no, I didn't know anybody at all. Oh, wow. Yeah, I didn't really know anyone. I knew Jeff Rossoss that's not true i knew jeff ross the executive producer the executive producer yes and i had met conan

at a simpsons party like oh gosh maybe a year and a half before he got the job and that was pretty much it those were were the only people I had known. Oh, wow. Did he remember you from that party? Yeah. I mean, I remember going to this party at some one of the I don't know which writer's house or apartment and meeting him and thinking he was very funny. We hit it off. And then I remember talking to Jeff Ross, who is in L.A., auditioning with Lorne, different people for the job for the host. Oh.

And he called me and said, I said, who are you looking at? And he said names like Paul Provenza, Alan Havey, comedians, basically. And then he mentioned some writer named Conan O'Brien. And you were like, you got to go with Conan. I said, I know that guy. I've met that guy and he's funny. And that's a different, that's, yeah, that's, it's refreshing to have somebody who's not a comedian. At that time, it was saturated.

Everywhere you looked, it was a comedian. Yeah. You didn't see a fresh-faced writer. Right. With his own different sensibility. Yeah. And he hit it out of the park. Well, I feel like you putting a bug in Jeff's ear was the reason.

Yes, I'm the reason. Yeah. I'll take credit. So then when did you have to show up at Rockefeller Center? For me, it was the day after the 4th of July weekend. So I guess it was a Monday holiday. So whatever the Tuesday was, July 5th or 6th. And he had called me, Robert Smigel, the original head writer,

had called me, I guess, the Friday before that and said, how fast can you be here? And I had to be at work days later. Oh, wow. Had you submitted a packet or how did you, because there was not a show yet. So how did you know what to write for? There wasn't a show at all.

I got lucky in terms of a packet. I had a friend who had been hired to be the head writer on the very short-lived Chevy Chase show. Because before that, I was trying to write sitcoms and all. And so I'd done a late night type packet for the Chevy Chase show. And then at the time, I was in a basketball game with a bunch of writers, some working, some not working. And one of the guys was this guy, Bob Odenkirk, who now is well known. But at the time, he was just a writer friend of Conan's. And he said, you should submit to that show. And I never heard of him or anything. Odenkirk put in a good word for me. So Robert Spiegel read it,

and they liked it. They still made me go through a second round of submissions. When that happened, they called me and Robert said, well, actually, Conan wants to talk to you. And Conan got on the phone and he was like, your first submission, it was exactly what we're looking for. It was perfect. And then your second submission, it's a pile of shit. I mean, what were you thinking? Why did you send this to us? This is awful.

This is offensive. You're wasting our time. And fortunately, I guessed right that he was joking. That was a test, yes. Right. So I just played along and I apologized and said, yeah, I knew it was bad. And I just got lucky that first time. And I am so sorry for wasting the time. And then I just started crying. And then Conan said, okay, okay. I wish you had flipped out at him and said, who the fuck are you? Who do you think you are? That would have been good. You're a nobody. Conan finally said, okay, okay, you can write for the show.

And that was that. Then I had to get on a plane. Wow. Wow. That's a nice way to get hired. Yeah. And Frank, you were hired initially to do guest segments, which is an incredible, I don't think anyone understands how much work is involved preparing, uh,

guests for the show. Yeah. We haven't talked about that much on. Yeah. Yeah. I mean, it's, um,

you want to try to prepare something that's entertaining. It's not always easy. You're on the phone with somebody and you're trying to, uh, figure out how it's going to work for however long the segment is you're talking about doing a it's called a pre-interview right talking to the guests yeah yes so early on when the show was starting some of the guests were were they wondering like who is this new conan guy or or were they just like oh you know it's another talk

show i'm ready just prepare me and i'll do. I think everyone kind of knew because it was so, you know, Conan was in the news. He was the guy to follow Letterman. Right, right. And everyone knew Sweeney. Is that your phone? It is my phone. That's unprofessional. It is unprofessional.

Is that a landline? That's also unprofessional. It was here when we moved in 10 years ago. We didn't get rid of it. You don't know how to turn it off. Frank, you're the one with the airplanes. Yeah. So I have a question for you, Frank, because I understand how they put together the writing staff.

Like Conan and Robert were trying to find a lot of like-minded people. But I've always said that a big part of the flavor of the show right from the start were especially your segments. And I wonder if they had anything to do with picking you as a segment producer because you were injecting a lot of comedy that I don't think was normally seen at the time into guest segments. And where did that come from? I think that just came from me wanting to make it entertaining. And a lot of the ways I would get comedy onto the show through these guest segments was to basically tell Conan that it was the guest's idea.

And in that way he would, you know, how could he say no? That's brilliant. Yeah. I mean, it was foolproof. I've got a lot of stuff on that.

There's no way. You never worry. He'd ask the guest, like, how'd you come up with that idea? Well. That was just me trying to make things work, you know, back then. And every day in 93 was, you know, a fight for survival.

We were all sort of coming up with whatever we could to make the show as interesting as we could because we were fearing possible cancellation. And death. And cancellation. Right. And death. And death, yes, and death. So, you know, every show was a special, basically, and we were all there till late hours of the night, right? Right. Do each of you have a really distinct memory to you that kind of sums up the beginning of the show,

how crazy things were? This doesn't exactly address that, but sort of. I remember we did the first show. It was September 13th, 93. And we did the first show. And the fact that we pulled it off and it came off good, we were celebrating. And we actually did physically go celebrate the whole staff and crew. And everybody went over to the 21 Club in Manhattan.

Which is closing. Yeah. Oh. Was that right? It just closed. Oh, that's sad. So we had a whole fun night. And then it was like, okay, we have to go back to the office because we've got to do

another show tomorrow and the next day and the next day. In fact, the first 15 weeks of the show, we did five shows a week for 15 weeks. And it was brand new. Think of it comedy-wise, we had no existing bits that we could refill. We were just creating everything as we went. So it was just this insatiable monster for content that we had to feed. It was fun, of course. It was tons of fun, but it was a monster. So you didn't go out and have celebratory dinners after every other show? Every night.

No, for the first 15 weeks. Every night. You've got to keep it going. But the writers would eat dinner together at the show, right? Yes, yeah. The writers would have dinner, and then we would work for two or three hours more after dinner. And then we'd go home, and we'd sleep, and we'd come back. And we didn't have to be back crazy early in those days.

In fact, the writers, I don't think, had to be back until like 11 or something. 11? That's crazy. I know. I think that's right. You had to rehearse everything at what time? Like 1 or 2 o'clock? We would get in.

We would get in just in time for the morning meeting. Then I think rehearsal probably started like an hour later. Yeah. So we had to have all our ducks in a row when we left started like an hour later. Yeah. So we had to have all our ducks in a row when we left the office the night before. Right. And there were no emails. So you had to leave endless messages for all the departments, very specifically listing exactly what you need. It got much easier when computers were invented. Yeah, no kidding. Were scripts just getting printed up and then passed around?

Sure. If you wrote something, you'd put it on a floppy disk and you'd bring it to the script coordinator, you know, and script supervisor and, you know, they'd sew it all together. Yeah. It was primitive times, Jesse, primitive times. How about you, Frank, like from the beginning of the show, any one memory stand out? There were always the, you know, the nightmares like Eartha Kitt. Do you remember Eartha Kitt when she was on the show? And she kind of slammed Conan. She gave it to him real good. I remember hearing about it when I started work there.

It was just like, oh, the worst interview so far. But it was just her being Earththa Kitt. It wasn't like anything she, that's just how she was. She was just somebody who, her sensibility was to give the host a hard time. But at that time, Conan, it was, everything was so sensitive. He was probably insecure.

Because Conan was insecure. Because he was just starting out, so. Right. Oh, so then it was uncomfortable because you could tell that he was not rolling with it. Everything she said was penetrating. Yeah. Right. She probably would have given Johnny Carson the same hard time.

Right. But at that time, Conan was so green. The other thing was, I'll never forget when John Tesh came on with the Zappas. Do you remember this, Gordo? Sure. And played this Black Sabbath song. Mm-hmm. The Wizard, John Tesh with his Frankenstein-like physique. That keytar, that keyboard that he wore around his neck.

Oh, right, he played the keytar, yeah. And then there was a woman in a soundproof booth. All this was going on, and it was completely insane. And I felt like this couldn't happen on another show. This was a completely surreal, weird moment. The other thing is like, it was literally like a week on the show. I had flown in from LA and I'm there a week and Dino Stamatopoulos comes up to me. He gives me a sketch to do called Brian Conano. Not an actor. I haven't acted, but here i am required to to perform literally a one-act play it was like back then we would do these these characters and they they were the longest sketches

they were almost saturday night live length middle of the show sketches they got shorter as the years went on i had to do this like six minute sketch and and i did but uh but that was like an example of what the show was like we would just throw anything against the wall and and the idea was basically i was conan's opposite you know he's six four i'm five three you know he's irish catholic i'm a jew right his hair went with the wave one way mine flipped the other way and right so were you coming out and confronting him or he just basically interviewed me and everything about me was the opposite of him. Okay. Right away I knew this was a show that was going to be completely off the wall. And we were doing characters. We were trying to not be like Letterman, to not do anything that they would do on that show, which, you know, limited us in some ways, but, you know, obviously inspired us in other ways.

Yeah, because Letterman was so famous for doing found comedy and, you know, a lot of his staff would be on the show, but everyone was playing themselves. And everything on this show at that time was written. Right. We would do fake characters, which he would never really do. Letterman. Yeah, except for Chris Elliott. Right, right, right. If I remember correctly, the network hated our characters because we would come on and

we would pretend they're real, but it would all be scripted. Especially Brian Conano. They hated that one specifically. But I think they thought that viewers were genuinely confused. scripted. Especially Brian Conano. They hated that one specifically. Ha ha! But I think they thought that viewers were genuinely confused. Like, they didn't know that this was scripted. We never, you know, stepped back and said, this is a bit.

We just pretended this is a real person, and, you know, we wrote it, we thought it was fun, and they thought, people don't know what's going on on this show. It's performance art. Oh, because early on, a lot of the characters would kind of sit down and Conan would interview them, right? So that's where the confusion might have come in.

Exactly. Oh, yeah. It was years later, I created a bit called Guests We'll Never Have Back, where we got to have fake guests, but we were presenting them in a palatable way. Right. You'd pre-tape them, and Conan would make it clear. Right.

He would say, here's a guest we had on, but, well, it didn't work out. Take a look. And, okay, we know it's a comedy bit. Right. I was just going to ask, when did the character start appearing in the audience? I think really early.

I think right away. Yeah. Didn't we have Robert Vaughn almost the first week in the audience? The actor Robert Vaughn, yeah. Yes. The original man from Uncle. We would have taped him probably over the summer before and then started using those bits of tape.

Yeah, so right from the start. He would stand up in the audience and give these eloquent speeches, which I think Andy Richter wrote. There would be no back and forth because it would be a tape roll. We would just have these little bits of tape of Robert Vaughn standing up and making these pronouncements or whatever. Then Conan and Andy would pretend that they're reacting in real time. It was later that we started having real live people interrupting from the audience, but probably not much later. Okay, got it. And you mentioned Andy being a writer. He was

originally hired to be a writer on the show. He was the first writer hired, yeah. But not to be the sidekick. That kind of evolved as you guys were putting the show together, right? Yeah, we were doing little test shows. Our studio wasn't ready yet, so we were doing test shows on Bob Costas' set. He was doing his late night show back then. Later. Right. So Conan started to practicing interviewing people. He would practice interviewing staff members.

I think he interviewed actually Andy as just one of the writers in one of the first pre-test shows. And then I think it was the second of those where they tried out Andy as the sidekick. And Andy was hilarious. I remember there was one moment where we all knew he had gotten the job where some prop or something came out or a box or something or something. I just remember Andy suddenly bludgeoning at the line, he's got a gun! And the whole studio fell down laughing.

And everyone said, oh, okay, Andy should be the sidekick. And from that moment on, he was. Wow. Bell down laughing, and everybody said, oh, okay, Andy should be the sidekick. And from that moment on, he was. Wow. Do you remember this bit, bitter, bumped guest? Yes. Who was, like, bumped every day for a week. Oh.

And then did we have him come out on the Friday? I think he came out for like one minute. That's all we had time for. Either that or, I could be making this up, but maybe Conan said on Friday, even then, sorry, we didn't have time. We'll have one next week or something. And he came out at the end. I think we, I do remember seeing him, but we never heard him. Maybe the credits were rolling and we saw him arguing with Conan or something.

Right. Yeah, yeah, yeah. I think so. Yeah. That's another example because everyone that this guy seemed like a real guest. Right. We never let on. Right.

Would you see him at the end of each show? Like Conan would apologize to him and was there a camera on him looking pissed? He was in the green room. That's great. And Conan would apologize at the end of every show. Yeah. There were a few bits that would last a week. I remember watching, I think it was Andy Richter was running the New York Marathon.

He was still running it the whole week after it was over. I think they'd check in on him every day. He'd just gotten a little further. Yeah, he was still working his way through the city. No, I used to love those bits that would actually, you know, thread through a whole week, which was fun. Yeah. We did that once a few years later with, we had a giant whale costume.

That was mine. That was Herbert, right? Oh, great. Yeah, yeah. And we used it for one sketch, and it truly did cost a fortune to make. Did you come up with the whale week on Conan? Yes. And we just came up with arbitrary ways to use this whale costume.

The best one was, I think, the next to last one, which was a Brian McCann idea, which was somehow he worked in bowling. Oh, yeah, the whale itself was the bowling ball, and we put it on some kind of dolly or something. And then McCann, with one of his wigs, was the bowler, and he bowled the whale down the whole hallway on the sixth floor. And it managed to turn the corners and then enter the studio and then knock down a bunch of pins. That was a good one. And then I think one night Will ferrell crawled out of it

as robert goulet right the last night it was like you know it's the last night let's let's you know say thank you to the uh to the the guy who's been inside the costume all week operating it come on out and then will ferrell came out but of course it was will ferrell as robert goulet okay and then he came over and did panel as robert goulet. Okay. And then he came over and did panel as Robert Goulet. Oh, great. That sounds perfect.

Do you guys have favorite memories of when things went horribly wrong? Because sometimes those are the most memorable stories that stick with you.

Mm-hmm. Yeah, yeah. There's the famous story of, you know, Abel Ferrara leaving in the middle of the... Who was a movie director. Movie director, yes. There's the famous story of, you know, Abel Ferrara leaving in the middle of the... Who was a movie director. Movie director, yes.

Independent. Very independent movies. King of New York, I believe he made, and Band of Lieutenant. Right. Yeah, he left. I mean, it's been talked about recently how he took off in the middle of the show. He was supposed to be the second guest. He bolted. Before he went out there? From his dressing room? Oh. From his dressing room, and he didn't want to go on.

And I had to chase him. I mean, one of the reasons why they hired me is because I'm pretty fast. So I'm able to outrun the guests, especially early on when Conan was a little, you know, unproven. So I stopped many a guest from leaving the building. Had he made it out of the building? In the elevator, he whispered in my ear, I'm going home to my mama. It sounds like someone's dying words.

I tried to talk to him about what can I do to get you to go back in the building to do the show. And he wanted a drink. So I bought him an anchor steam. He guzzled it. And then he went back in the elevator. Oh, he guzzled it before he even. In the lobby of 30 Rock.

Oh, wow. He gave me the beer bottle and walked out of the elevator and did the show. And it was a memorable interview. What about you, Gordo? You put me on the spot. You have any nightmarish moments? Yeah, I have various nightmarish moments. There are so many times where bits that somehow survive rehearsal and get on the show, which is the main thing. And then, oh, you know, for one reason or

another, the audience doesn't like them or something goes wrong. But actually, the things that occur to me are more like rehearsal things where you bring something to rehearsal that you think is great. And then it's like, oh, no, it's so not. I remember once I had a, Sweeney will remember this, I'm sure, or maybe Jesse too. I'm not sure exactly when it was, more recent times. But there was a news item about some ice cream manufacturer making cicada ice cream. And they were actually putting real cicadas into the ice cream. And I imagine they were grinding them up or something. And so I thought it would be a funny bit if Conan talks

about that and says, isn't that crazy, Andy? We cut over to Andy and there's Andy and he's eating ice cream, but it's got what looks like real cicada parts, you know, sticking out of it and he's crunching away. It goes, hmm, this is yummy. I thought that would be funny. I'm going to turn out to be wrong. We had the seating department do an incredible job of making all these, you know, fake cicadas that looked real, but that also Andy could eat. And I was so pleased with their work and the ice cream looked great.

And we did the bit at rehearsal and Andy crunched into the cicada ice cream. They got absolutely no reaction from anybody in the studio. We cut back to Conan, who's looking at the cue cards. Okay, where does the sketch go now? Oh, that's it. That's the end end it was just what i thought would be a hilarious sight gag and it wasn't oh you know conan can be fantastically sarcastically cruel in a funny way at rehearsal this is my favorite he just stared at the camera for a long time and then backed away from the camera and then ran and he ran out of the studio and he was gone for a couple of minutes and then he reappeared run all the way home he reappeared at the top of the stairs he had gone all the way around and come up the back and appeared at the top of the audience and he came down and he just sat for a while in the aisle with his head in his hands. And I have pictures

of it because, you know, we have a photographer who takes pictures at rehearsal and I said, I have to have those pictures. And I look at them every once in a while to remind me. It doesn't always go as planned. I mean... But that's such a magnificent failure. It really turned it into, yes, kind of a compliment in a way to get that level of reaction.

What about you, sweetie? Listen, I'm serving as a host. If you want to book me as a guest on your podcast, I'll be happy to tell you many horror stories. What if things that went wrong? Yeah.

I remember the last beat of a desk piece involved we we we used live animals a lot on the show uh needless to say and um one of them i forget what the beat was but it was a cat it might have been a cow doing ventriloquism and it was the last big beat it was the big topper before conan would throw the commercial and the the bit before was happening steve hollander the stage manager came up to me and he goes um we don't have the cow it's like wait what do you what do you mean we don't you know we just rehearsed with the cow where's the cow?

And he just shrugged his shoulders like, I don't know. I was like, you've lost the cow. Conan started to introduce the cow, and we were shaking like, and he's like, what, what? And we're like, no cow. He was as baffled as I was, and he just, I don't know if he ad-libbed about it or he threw it to commercial. And what happened was, i didn't know this once the show starts they take the cow outside to go to the bathroom so there isn't an accident during the show even though that would the cow having an accident during the show would be vastly preferable oh yeah so the cow broke the elevator it went down and it broke the freight elevator.

So it never made it back up. It broke the freight elevator? Yeah, freight elevator in Rockefeller Center. Apparently it was not built for heifers. Just even saying it out loud, it's like, oh, who cares? But at the time, you know, with the audience there and the cameras, you just feel like, oh, my God. It's all my fault. We failed to deliver this cow behind the curtain.

I'm glad I asked. I was curious, Frank, could you run us through, because I don't think we've really talked on the podcast before, about prepping a guest for the show? Because I think, you know, people who watch at home just assume that every celebrity is very hilarious and has off the cuff stories because that's how you make it look. Right. So I'll get somebody on, on the phone, like for example,

Sienna Miller, cause she was the last one I spoke to. I'll have some research, but just the way you guys have research in front of you, I'll talk to her for as long as I feel like I need to, until I have what I think is an entertaining, hopefully, entertaining whatever it is, seven minutes, eight minutes, 12 minutes, whatever it is. And then hopefully I'll have either anecdotes or something from the guest, not always the case, and talk to Conan in a meeting. We'll have a segment meeting and we'll kind of

go over it, maybe come up with ideas that are funny. Now, sometimes you don't get anything and then you have to generate the ideas yourself. Things that you think might work for Conan that he could be funny on or that the guest might, you know, or you might come up with a bit like Gordo was referencing earlier i used to do it more in the early days i don't do it as much now because conan is the greatest interview in the face of the earth right folks are you with me sweeney you agree yes of course same page there's no pops and whistles really these days but that's basically it so then we'd have the meeting is big you know you have the meeting with other producers, you go over the notes, whatever it is

that I've prepared with the guest from that pre-interview. But Conan is very loose and things tend to spark off of the notes and off of the questions. And that's where the gold is. Because, you know, when things go off the page, that's your hope. And if things become organic, that's what you want. And all of the other stuff, in my opinion, like the preparation is just a safety net for everybody to be relaxed. Yeah, that's a good way to put it. Conan knows there's something that the guest has, and the guest knows that they have something to talk about. But then they're able to loosen up and be in the moment. I hope I answered the question. Yeah, definitely.

No, that's a good answer. By the way, I did a pre-interview with myself before I went on tour. I was wondering if you would. I was so bad. I was going to tell you guys to cancel me. This was our safety story. Yes. You went back to yourself and said, he's got nothing.

I had nothing. I tried so hard with myself. No, but I think this is really, it's really interesting. And I mean, you are also a writer. I tried so hard with myself. No, but I think this is really, it's really interesting. And I mean, you, you are also a writer. So you do often come up with funny ideas for funny guests. But I think people often see people, see the guests come on and think that they've done that work to make themselves funny. And really, it's. Sometimes they do.

I mean, there are guests that will, that will come loaded for bear, you know, and that's those like Martin Short. Those are the guests that you those are the guests that you dream about. But look, everybody wants to do well on a talk show. Right. Well, Conan always said he liked comedians because they kind of understood what was expected of them. So they would, yeah, meet you more than halfway and try to come up with a lot of stuff. I always got the sense you enjoyed,

you'd get extra excited working with comedians too. That's where you're wrong! I despise comedians! No, you're right, you're right. Comedians, yes, they're always, usually, not always, more fun. Yeah, yeah, yeah. Someone like Tomedians, yes, they're always, usually, not always, more fun.

Yeah, yeah, yeah. Someone like Tom Hanks, right, Frank? Because he would come on, he would put himself in your hands, and he would totally commit to doing whatever, and he would be great, and you'd always come up with really good ideas for him. So that was a great combination. Yeah, I could do anything to him, and he wouldn't say no. Remember the dropping snow on his head or soaking him with water.

I mean, he didn't care. Whatever you want to— Oh, right. We had a new set with water in the background. Oh, yeah. It was the whale breach where he was completely— He's like, look, a whale. And you nailed him with a bucket of water.

So you made it a personal challenge to get Tom Hanks to say no to something. I haven't succeeded. He won't say no. Didn't you hit him with a wrecking ball? I did. And then he went through a car wash. I don't remember the car wash. It was like a desk drive.

Oh, wow. Oh, fun. A desk drive. Do people remember desk drive? Those were so hard to produce. Those were nightmares. You want to explain what that is? We used to do it a lot in New York, and they were really rough rehearsals, but they would be great, great bits.

Yeah. And it basically was Conan and Andy, or Conan and some other guest, sometimes someone we plucked from the audience, but Conan and somebody as his co-driver with a green screen behind them. And then we would shoot all this footage and they would pretend that they are, you know, in this footage that we would, you know, build in all these jokes. Some of the jokes were in the footage and then some of the jokes were live actors who would come out next to the desk and interact with Conan and the other person. And, you know, the timing, you know, was sometimes kind of bang, bang and stuff, which was tricky because you want things to be loose and you want things to be able to breathe.

But they always turned out great. It was a really fun, impressive sort of bit. The crowd loved it. Yeah. The shooting and the rehearsing of it was always tough. Yeah, but the payoff was big. So it made it worthwhile. But speaking of characters, you guys

have both played characters on the show. Gordo, Michael Gordon, I guess your most famous character, it's your headshot on IMDb. Yes. Was the masturbating bear. Yes. I think that's by far my most famous character, considering I'm not even a performer. You know, all the other writers are stand-ups or improv people. They're really talented performers. And I can't do any of that. I can't be trusted with the line. But I'm pretty good, if you can't see or hear me.

At masturbating. Yes. I'm so good at it. And so, yeah, I played the bear for a million different times. How did that character come about? I don't think I know the origin story for Masturbating Bear. There was a great writer we had on the show named Brian Rich. And we used to do a bit called Pleasing the Affiliates.

And we would make up these demands or complaints from different affiliates around the country. And Brian Rich made up a complaint from, I think maybe the station was in Cincinnati. And they were complaining, they didn't want to see the masturbating bear again, which he just made up, you know, out of whole cloth. And Conan said, okay, fine, you know, we're gonna have the masturbating bear on. But from now on, he's gonna be chained. So the first time I came out, it was supposedly, you know, the multiple time I've come out. So I came out and I'm wearing these, you know, these bracelets, these bracelets, and I've got chains. And Sweeney and Brian Rich played the attendance with these, you know, electric cattle prods to keep me under control.

And then, you know, it always ended the same way. I would break free and they would start zapping me and I would fight back and masturbate at the same time. We were told by NBC, you can never do that again. And so we waited a few weeks, but then we started doing it again. And then we just started doing it a lot. Yeah. Wait, did NBC say you can't do it? Did someone say you can't? The first time. Yeah. The first time I think they said, don't do that again. We'll let it go through once, but you can't do it again. Oh, I didn't remember that. It just made your lust stronger. They lost interest after two weeks, apparently. All of a sudden, it was fine to do again.

And that was a fun character to write for because you come up with different things. I think one of the best ones was when we did a week of shows in Chicago the first time. And Michael Komen, one of the writers, came up with the idea that we had left the bear behind. Komen was going to have a classy show in Chicago. We left the bear behind. There's no way he can get here. And then suddenly we hear an airplane up above, and we cut to footage. And we got a skydiver to put on the bear suit and jump out of a plane over Chicago. And we got this gorgeous footage of the bear drifting over Chicago and landing. And then as soon as he hits the ground, it becomes me in the bear suit. And then I run through Chicago and have some, you know,

little comedy things along the way. And then I burst in live into the studio and run through the crowd, which was going crazy, which was very nice. And I had to go up the stairs, which is really hard. If you've ever worn a bare head, you know you're only looking through the teeth to see, and you can't really see much. But I had to negotiate these stairs and then scamper across the stage and get right next to Conan right when the music ended. And that was the best thing probably I've ever done in my life, that I got the cue just perfectly. I got there just on time. And then you take a beat, and then you start masturbating.

And it was a great moment. Always take a beat before masturbating. Jim Carrey played the bear once, too. Jim Carrey, I coached. Jim Carrey was fantastic. He wanted to come out, and he did. He came out as the bear on the show, and he wanted people to believe it was me until the head came off.

And so he had me coach him exactly how I crouched, exactly how I did everything, because he wanted to do it exactly right. So I really respected his craft. And then at work, he came out out and Conan interrupted him and made him take off the head. And it's Jim Carrey. And, you know, the crowd went wild. And some people I read online were saying, has it always been Jim Carrey? I love that. He's not good at prioritizing his career. Well, I just was curious, because you brought up Jim Carrey. And I mean, both of you have worked

with so many celebrities. And you were talking about Tom Hanks earlier, Frank. Was that an adjustment to have to start, you know, where you're directing celebrities that maybe you're a fan of? Have you ever felt intimidated or? I think when you when you have a job, when you're responsible for something, that you lose all of that. You know how things are. You just want to make sure it works. So being starstruck just disappears,

and you just are thinking, how is this going to work? And how is Conan not going to lay into me after the show because it laid an egg? I think that's what it is. I mean, you just have a job to do, and you focus on it. You don't want the fact you're dealing with Dr. Ruth. That time I was a little bit nervous. I was nervous when I worked with Dr. Ruth.

I was definitely, I couldn't even speak. Frank, you played in one of my favorite clips. I think it's a lot of people's favorite clip is you as Mother Teresa. Oh, yeah. Yeah. Pitching a hissy fit in her hotel room. It's a classic.

Well, what's your question? It's not a question. I was paying you a compliment because it really is. Well, thank you. I appreciate it. That's very nice of you to... But I will throw one right back at you because I think Money Shot Lincoln may be my favorite character. I mean, that's fantastic. A band named themselves after that character. Is that right? Money Shot Lincoln?

Yeah. Oh, that's great. It's just the actor in it. It was Brian McCann's bit. And I was like you, Frank, with guests. I really wanted to do a good job. Mother Teresa. Yeah. frank with guests i really wanted to do a good job mother theresa yeah i mean i guess that happened because andy blitz came up with that idea oh it was was that an andy blitz idea and he probably thought uh frank looks the most like mother theresa which is probably true right on the staff

yeah and then i just went crazy well it was a great setup for you because you know you like to roughhouse i do they set up a hotel room where you were allowed to destroy every single thing in the hotel room oh that's so much fun and it's just you on the phone with the front desk going i was supposed to get a wake-up call why no wake-up call and then you just start banging the phone you tear it outup call? And then you just start banging the phone. You tear it out of the wall, and then you just literally total the room. It's great. It ended with you taking the TV off of the wall, I remember,

and throwing it across the room, which was a great touch. That's the thing where I was a complete asshole because I refused. They had that set with the breakaway everything. Lamps and you name it, glasses and frames. I insisted that they bring a TV for me to smash.

I actually walked away for a little while and told Jason Shalemi, until you get me a TV, I'm not doing this. Wow, what a diva. I was a complete a-hole. I was like in character as a difficult Mother Teresa. Yeah, that was fun. I wish I could do stuff like that every day. You and I, Sweeney, I think are responsible for breaking Conan's hand.

I was going to bring that up. I'm glad you did. Yeah, I'm glad you did too. I don't think I've heard this story. I don't think he actually broke it. it what was that bit it was i was heckling you right i was a comedian wow this is close to real life i was a comedian i was bombing and you were heckling me and then we start going back and forth and i run up to fight you yes we're wrestling on the staircase and we were kind of really wrestling. Right. And we were really wrestling.

And then Conan comes up to break it up. I mean, it's his fault. He jumped in. Yes. And then he went down the stairs of 6A. Right. I think he pulled the ligaments in his thumb. So he barely sprained his hand.

He didn't break it. Yeah, yeah. No, it didn't break. It didn't break. But it was screwed up for several weeks. We have a question we like to ask all our guests. And you two... Are no exception.

What kind of advice would you give to people starting out in this line of work, the entertainment business? I would say to not be lazy. Just always work hard because it doesn't always pay off when you work hard, but it kind of always doesn't pay off when you don't work hard. So especially when you're starting out, I think victory goes to the least lazy sometimes. So, you know, inertia is a tough thing to fight, but just push through it and just make yourself work hard. That's what I'd say. It's very honest and well put. That is great advice. Frank?

I would say just don't give up. Persevere. Keep doing it regardless of how many times you fail, if that's what you want to do. And realize that failure is all a big part of it, and eventually you will get there. That's good advice, too. Also well put.

Accepting failure is, I think that's a hard thing to learn. You just assume. Yeah, resilience. Sometimes the first thing goes wrong. It's like, oh, that's it. This isn't for me. It's a sign oh, that's it. This isn't for me. It's a sign. Yeah. So yeah, you got to push through that. Well, that's great advice. Thank

you guys for appearing together on the podcast. I know. Thank you guys, Sweeney and Jesse, for doing such a good job. I love this show. Yeah, it's a good show. You just got rebooked. Frank just heard about it today. Yeah. Frank's still on the fence. I don't blame him. And that was our interview with Michael Gordon and Frank Smiley, two very legendary Conan writers, producers. Oh, yeah.

It was a pleasure talking to them. And now we have a fan voicemail. Yes, someone figured out how to use their phone feature. Hey, whatever happened to that masturbating bear? That sumbitch is funny. Anyway, I'll hang up and listen. He thinks he's calling live radio. I'll hang up and listen so there's no reverb. He didn't mention Conan either, so we don't know if he was just calling like a hunting tip line or anything. That's right, the National Park Service.

He thought he was calling Yellowstone National Park. Yeah, that son of a bitch was funny, he said. I like his familiarity with him. He got me too'd. He did get me too'd. Because he did do it in public. Right. He was very public about his masturbating.

What happened was, obviously, we left NBC, and then it was like, well, let's not even get into trying to carry some things over. Although some things we carried over, but I think the thought was... Well, he did come back once or twice on the DBS show, didn't he? Yes. He made one or two cameo appearances. Just for sentimentality's sake. Yes.

Well, I guess we could explain. So after the show left NBC, technically a lot of those characters were the property of NBC. Say the full term intellectual property that's right there's a lot of intellect behind a bear that masturbates with a a giant diaper yeah i know and the way that it masturbates like it really was upsetting really it's hilarious but i i just like did it bother you the way he'd kind of flip the outer curve of the sack?

Yeah, the flopping. It was just so much bulk in there, too. There was a lot of bulk. It seemed like he had elephantitis of the testicles. Yes, yes. That's what I think. And I think I was imagining that maybe he had some sort of infection. It seemed more like an itch.

Bears would go extinct if their genitalia was that large. It's just out of infection. It seemed more like an itch. Bears would go extinct if their genitalia was that large. It's just out of proportion. Yeah. I feel bad for the caller, but he can watch, there's I think a ton of masturbating bear clips online.

Yeah, just Google masturbating bear. Right. Did the masturbating bear, he never went to jail or anything, did he? In real life? He would be caged. He got frozen in carbonite. Oh, okay.

I think that's why we really didn't bring him back after late night, because we had a big ramp up to the end of his appearances on late night. He got frozen in carbonite. Yeah. Actually, the star of Star Wars, Princess Leia herself, Carrie Fisher.

Carrie Fisher? Came in to release the masturbating bear from carbonite. What? Yes. You got Carrie Fisher to do that? Carrie Fisher came in, saw the masturbating bear in carbonite, and she released him. And then he ran off into the wild to live forever after. Oh, yeah.

Well, you don't want to mess with a beautiful fairy tale ending like that. So we couldn't bring him back after that. Yeah. No, that story's closed. Well, thank you, caller, whether or not you meant to call in to Inside Conan. I hope you got your answer. Yes, anonymous caller. Yes.

I picture him hanging up the phone whenever he left that message like two weeks ago and just sitting there listening. Sorry about the two-week wait. And that's our show. That's our show. I hope you had a nice Christmas if you celebrate. You can go back to your family now. I hope you had the day off and you didn't have to work the way we did. Yes. And we'll see you next week. Yeah, we'll see you next week for New Year's. Oh, you're our date for all these important holidays. Well, that's appropriate because...

We like you. Inside Conan, an important Hollywood podcast is hosted by Mike Sweeney and me, Jessie Gaskell. Produced by Jen Samples. Engineered and mixed by Will Becton. Supervising producers are Kevin Bartelt

and Aaron Blaire. Executive produced by Adam Sachs and Jeff Ross at Team Coco. And Colin Anderson and Chris Bannon at Earwolf. Thanks to Jimmy Vovino for our theme music and interstitials. 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, 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. This has been a Team Coco production in association with Earwolf.