Inside Late Night With Mark Malkoff Ep 3: Robert Smigel

Robert Smigel has been responsible for some of the most memorable and inspired late-night TV of the last four decades. From his long association with Saturday Night Live, to his creative partnership with Conan O’Brien, the man who gives voice to Triumph the Insult Comic Dog is a late night hall of famer if ever there was one.

In this episode of Inside Late Night, Smigel joins Mark Malkoff for a free-flowing conversation about his many years at 30 Rock, from the origins of two Steve Martin sketches that are among his proudest, to the time he says Lorne Michaels forgave him for “almost breaking” the show.

The two also discuss the evolution of the Late Night with Conan O’Brien remote, the art of the pre-show audience warm-up and how it contributed to Conan making Late Night his own, backstage tensions at SNL, and more.

Smigel’s most recent projects include the Netflix original animated film Leo (which he co-wrote and co-directed), and the YouTube special Triumph Presents: Let’s Make A Poop LIVE From SF Sketchfest.

Click the embed below to listen now, or find Inside Late Night on Apple Podcasts, Spotify or wherever you listen to podcasts.

Show Transcript

Mark Malkoff: Robert Smigel, thanks for joining us. 

Robert Smigel: You’re very welcome. 

I have known you since I was 17 years old and I have all these questions I’ve never asked you.  [You recently released the Triumph Special] Let’s Make a Poop from Sketch Fest. I’ll read some of the reviews later, and talk about the show, but people love it. I mean, joke by joke, the amount… It reminded me of Rodney Dangerfield a little bit because it’s joke-joke-joke. Like kind of like a machine gun of jokes, which is really hard.

Yeah. Well, that’s Triumph. He’s an old school comedian, you know, so he’s rat -a -tat. From the school of rat -a -tat. 

Yes. I want to start, because it was such a pivotal time for you, and also Conan, and Saturday Night Live, which is: The fall of 93. When they launched Conan, you’re the head writer. What are your hours like? Are you doing 12, 14 hours a day more? 

Yes. I probably, probably around 14, I would say. 

So you’re doing 14… 

I would say, I would come in at around 10, and there would be a morning meeting and then we would get to work on that show, on future shows, because, you know, talk shows now they do four days a week, but the Conan show was five days a week, and that is an enormous difference. 

And you guys were doing ambitious things. 

We were like, you know, five days a week means one more hour of shows to fill, and one less day to just focus on material and not production, and so It was a much… it made it much harder and they, you know, about three years in, I think that schedule changed but but yes so we were there I would come in at around 10 and if I was lucky I would leave at 10, but you know… 

This is my point. You had just gotten married to Michelle, you’re working these crazy hours but yet you are still writing sketches and submitting on top of that to Saturday Night Live.

Occasionally I would do that. 

I would see you over there. And like, I mean, I remember for like Kelsey Grammer, you wrote an inhibited dance party. You and Michelle were extras. I remember “Motivational Speaker” the first time we ever met, which was Sally Field, which was Santa, the motivational speaker. You worked on that. 

Michelle and I were extras in that sketch? 

100 percent.

I don’t even remember that. I’ve got to look that up.

Oh, you know, I don’t know if it’s online, because so many of these amazing sketches had music. 

It’s not. But I have an SNL database that I got from somebody who was working on a Jim Downey documentary that may or may not come out. 

I hope. I’ve heard about it. I hope it comes out, but you should look that up. My point is, you’re working these crazy hours, and I thought for sure that Lorne Michaels asked you to come back to write, because they were having a really tough year They had lost everybody: you, the Turners, Christine Zander. They had lost Jack Handey. It was like the power players So I thought Lorne asked you to come back, but that’s not true? 

No, nobody asked me for anything. I just, when I had an idea, you know, I missed working there on some level. I likened it to a gambling addiction 

That’s what you told me once. You said I was like a gambling addict is what you told me. 

Yeah. Well, I remember watching the first show that I wasn’t there for which was Charles Barkley and ironically I had a sketch on it.

Which one?

Oh, I think it was called. “Is that a guy” or something? It was a game. 

Yeah, I remember that, is that RuPaul?

I don’t even remember, but it was like a thing that, like, you’d never do now, but back then people just casually would be like, “that’s a dude, that’s a dude,” but we just made a game show with crude panelists. But yeah, I would. If I still had ideas, because I couldn’t resist writing them up and sh*tting them out and putting them on the show. Damon Wayans’ show, I had like two sketches on. 

Which one was yours? Was it the trumpet one? The jazz musician?

Oh man, you have a scary memory. I had the one about summer camp with all. 

Oh, yes. That was right after the monologue. That was Ellen Cleghorne and Tim Meadows. 

Yeah, that was, maybe that wasn’t Damon. Oh, no, John Goodman’s show. I had two sketches on. I had to.

I was there. You did Tom Snyder and you did The Bears and you did the dog with Sandler. 

Tom Snyder, I don’t think was that year. 

No, it wasn’t. It was the Bears sketch that you did. 

Yeah, it was The Bears sketch that I was in the dog. Yes, some some sketch where Adam was not a dog. He was a human. I don’t even remember the premise. 

That was the following season. But you were on the floor like jumping up and down in excitement watching Sandler play the dog. 

It was so much fun. I always watch the sketches live, because and it was always it always mystified me that the writers of sketches would just convene in the writers room upstairs and watch the show on TV. Like, for me, maybe because I just loved the job so much, maybe because I was a sociopath, one or the other, but I hated sitting in the room and just kind of Greek chorusing the show that way. I, when I had a sketch on Saturday Night Live, I always wanted to be an 8H to watch it live, right past the cameras, because it’s like that’s, I always felt like this is the only time I’ll ever get to watch this way. I can watch it on TV for the rest of my life. 

Did you ever have more adrenaline as a writer watching something from the floor than when you did that Steve Martin cold open: the Broadway number with the song? 

No. That’s amazing that you would pick that one out. Were you there for that one too? 

I wasn’t there. I had dress rehearsal tickets to see the show the first time, and I got appendicitis the day of. 

Talk about jumping up and down. That’s the one that I remember jumping up and down about. 

That’s what I was going to say. The best cold open I’ve ever seen. 

Aw, that’s nice. Well, you know, I did feel like a 10 year old watching it, and every beat working. And, you know, that sketch, I still get emotional when I watch that sketch. 

Younger people cannot believe that they would do a cold open without politics and I want to point out that Steve Martin/James Taylor show had no topical stuff. No politics, which, I really miss that they can’t get through a show now. 

No, that’s just late -night comedy 

Yeah, I guess things have changed, but my point is that you guys would have entire shows that weren’t topical which was–wouldn’t happen a lot, but I wanted to ask: For that sketch, that that Steve Martin cold open, did you pitch it on Monday? Did you know it had to be the cold open? 

That sketch was an idea I had when we were doing “Happy Happy Good Show” in 1988, which was a sketch show that Conan, Bob, and I did during the writers strike in Chicago with some friends of mine who had been in my comedy group in Chicago, before I got SNL. And I had that idea… I remember, just, I loved the idea of a big song about how we’re just gonna, we’re actually gonna give you guys, you know, a hundred percent tonight. But I never, it didn’t quite work for that show. And then Steve Martin just showed up, and I was like, huh, wait, this is the guy. This is the guy for this idea to sing passionately about how he’s actually going to make an   effort tonight. And so that’s when I started writing it and, and in fairness, I want to make sure, because it is one of my favorite things I’ve ever written, but it was my idea. But Zander helped, uh, Franken and Davis helped, and I believe there might have been more. 

The Turners had one beat, I believe. 

Probably. I don’t know. This is is turning into the William Shatner/Star Trek sketch. 

I know! 

You’re telling me about a horse I owned that just had a foal. 

That’s what Kevin Nealon said the last time I saw him, he said, “you know who you remind me of?” 

Myself in the Star Trek sketch. 

I can’t help it. 

It’s okay. It’s okay. 

I was going to say, did you know it was going to have to be the cold open or would it have worked in a different place in the show, do you think? 

No, no, it had to be the cold open. Had to be.

I do want to point out, that a Saturday Night Live writer pointed out to me, and this is absolutely true, that that sketch ruined the rest of the show. I mean, the audience was so… you should watch it. After that, they had so much laughter, so much energy that it just… the rest of the show died. One other time they tried something like that a little bit with Mike Myers hosting. They did a monologue with the song and dance, but they purposely brought the energy level down, because I think that they were afraid that it was just going to be a duplicate of so much energy. 

Yeah, that sketch peaked at the end, actually–the I’m not going to phone it in–when he says “Live from New York” and then he says “Line.” That gets a big laugh and then that you just get chills seeing them sing “It’s Saturday night.” 

Every single time. That happens to me, every single time. All I’m saying is, people, if you’ve never seen this thing: I watch it at least a couple times a year and chills every time. I just had appendicitis, and it was, you know that I told the doctors keep the TV on, and I woke up just as the show start started with Steve Martin in his dressing room and stuff, and I’ve never experienced something like that that was like, I don’t know, so Inspiring. So, I want to talk about Conan, when you thought the big change happened in ‘93, because I was going to the show–you would see me. There’d be empty seats in the audience, we would talk after every show, you were kind to me, we’d talk on the phone. You did save me, by the way, when I wrote that piece when Conan’s last show on TBS, I wrote like this Twitter thing about going, and you’re like, “This sounds like that fan fiction, but Mark Malkoff, it’s all true,” which was very nice that I was passing on some… notes so you were very kind to do that so I thank you. 

Listen, I really appreciated fans who appreciated what we were trying to do, because we were getting reamed publicly at the time, and the show meant more to me than any job I’d ever had not that I’d had that many. But, you know, Conan and I were given this opportunity to create this playground. and do the silliest stuff we ever dreamed of doing that would never work on SNL. And we were replacing our hero, David Letterman, and I just can’t imagine ever getting a job that would mean more to me than that. 

I’ve only met Lorne Michaels a handful of times, and he was telling me this story about how he wanted to open up the set of Conan and put in a window and the moon, and just to open up the set. And he told me your response, and what was it? 

All I remember is that we were trying very hard not to make the show look cliched like every other talk show with a backdrop of New York City. 

With like Letterman, yeah. 

Letterman, yeah, I mean, everything. I mean, both Lorne and I wanted to change the name of the show from late night to, I wanted to call it “Nighty Night,” he wanted to call it “Night Night,” which was better, but they had no interest in f*cking with their potential franchise, and they, you know, it all made sense, they liked the name “Late Night” and it’s worked for 30 years since, but I don’t remember if I had a specific reaction. 

He told me that you said “They’re gonna kill us… they’re gonna go after us,” because of  Letterman because of the window. 

He’s right I was hilariously paranoid about being perceived as doing anything that Letterman did [but] worse. For the first year, I always joke that I didn’t allow Conan to do remotes as himself because Letterman had mastered it, and I’d seen Dennis Miller try, and I’d seen… Pat Sajak try,and it’s like, “Okay, Conan’s not these guys.” I mean, well, Dennis is pretty damn funny, but I wasn’t even interested in giving Conan a chance, because I just wanted us to create our own path, just establish something very different and then maybe later on, then we can start bringing in ideas that bringing in, you know, ideas that are more derivative of other shows, but it was really scary to me to be, because I’d seen, like, Pat Sajak and Dennis do remotes, and they paled next to Letterman’s, and I just didn’t want to be put in that position. 

I have to say, though, the first one I remember, and I could be off if this was the first, was Andy Richter at Woodstock, which was really, really funny. 

Well, this is the thing, so… I was like, Andy can go to do remotes, but not you. We, that was the first thing I, I was like, let’s start sending Andy out because it’ll give Andy something to do. It’ll, it’ll give him more credibility as being your sidekick because he was getting all the sh*t kicked out of him. Yeah, I would send Andy out with specific premise-oriented sketch ideas that would be remotes. So, the first one was he went to the Grammy Awards, and all you care about, Andy, is that Thin Lizzy.. 

I remember. 

…has never been inducted into, has never received a Grammy, and all you want to do… So they were like obsession pieces, and that was his obsession, and that one, and then I sent him out to the NBA Finals. and I made him ask everybody, “What about the Horry factor?” There’s a player named Robert Horry. So on the Houston Rockets, when the Knicks were playing the Rockets, this is in mid ‘94. And yeah, what about the “Horry Factor?” And then we did Woodstock that summer, and that we opened it up a little more, and it wasn’t just a theme thing, because now we’d established Andy as doing funny remotes. 

He had a voice I think a little bit more that was the first one I realized like he kind of was finding his voice a little bit more than the others. 

Well, yeah, because he was I was letting him a little looser and not shackling him to a premise. It was all a gradual process and then Conan did his first remote that was kind of a Conan remote in September. of ’94 when he went to Sun Studios in Memphis. So there was a premise to that where he was wanted to be a country star. So there was still like, we were doing what we were doing with Andy with Conan now. We were like creating premises. 

Is that the one that Sting made a cameo on or was that a different one? 

No, that was a different one. That was a premise remote that… we would have him do scripted remotes. Even from the beginning, he did like scripted remotes and not that that premise was, not that that was entirely scripted, but it was mostly scripted. It was like a Curb Your Enthusiasm, like every scene was kind of planned out and they would improvise off of that. So that was Conan wanting to do a “We Are the World” kind of song called “Famous Helping People,” it was called. So it was him, and Andy, and Oldy Olson who we had already established in another remote, where during the baseball strike I wanted players to, I wanted to substitute baseball with games which were, we had like six-year-olds playing 80-year-old men, you know. surprisingly competitive. And so that’s where Carl ‘Oldy’ Olsen was created. And then we brought him back many, many times, but the first time was during this “Famous Helping People” sketch, which Sting was kind enough to do a remote in, I mean a cameo in at the very end. 

Conan would sing on this show, like the first show, but not a lot. 


That brings me to my next thing, which is that besides Letterman coming on the show in December of ’94, he premiered in September. 


That and other than the college audiences coming that summer. I think that those probably saved the show, but I would argue that the next factor after that was Conan changing the warmup. 

Conan changing the warmup.

I’ll give you an example. So he would come out and sing “Burning Love” Elvis Presley at the top of his voice and get such a, he would sing it to an audience, but then what he started to do that summer is take a woman from the aisle out and sing to her in the audience. And the audience just got so much more excited. Then he would be like, come up the band, we’re gonna dance in the aisle. And then Mike Sweeney came in. And you guys rid of Joel Goddard doing the warmup, who told me personally, I quote, “I was not very good at it.” And he did have a hard time. And then you brought Mike Sweeney, and I just felt the audiences that summer, it was night and day, is what I’m saying from September, when you guys started up until that summer, it was a different energy. 

I think there are two factors here. One is, I think you’re absolutely right that improving the warmup made a difference. The other thing that started to help was that, and Conan talks about this a lot, starting that summer the audiences were just more excited in general and that was because college kids were home and were able to travel to New York and actually, you know, so the audience was filled with fans. as opposed to people who were just there to… you know, because they couldn’t get into Letterman, and they wanted to see it and wanted to see a real talk show. So, it’s not that we didn’t have fans, you know, because you could tell just from watching, if you watch early shows, you could tell that like recurring bits, like Clinton on Clutch Cargo would get anticipatory applause from the beginning, so there were people who were fans watching our show in the audience but it became… but that summer it grew exponentially, because college kids were home.

One of the most interesting things I remember is Joel Goddard they gave him the warm-up because Conan had no real experience and they were afraid that any warm -up comic might be funnier than when Conan came out. So they get rid of Joel and then at least one time before Sweeney came in, I saw Louis C.K., then an unknown, do the warm-up, and he’s purposely not being funny. It was so strange to watch because, to me, it was clearly, he doesn’t want to outshine Conan, and I’m like I’ve I It was just such a strange thing because I’d seen that guy kill in standup clubs There was like no energy in the audience and he was always able to bring it up. But I thought that that was an interesting choice. He didn’t do it much I don’t think. 

That was something, when it came to behind the scenes and how the show works We were trying to copy Letterman. I believe Letterman had Bill Wendell do the warm-up all those years–not when he moved to CBS. He had Eddie Brill, a comedian, do it.

Bill Scheft did it for a while on that last couple years of Late Night. And early CBS.

Bill Scheft, yeah. But in the ’80s and early ’90s on NBC, I’m pretty sure my memory serves me right that Bill Wendell, the announcer, was the guy doing it. 

Yeah, Wendell did almost all of it, and that’s why you did it with Joel. October 23, 1999, Norm Macdonald hosts Saturday Night Live. Backstage, you are with Sandler. Norm brought in a couple of writers, including Fred Wolf, Sam Simon, Andy Breckman. What was it like backstage? Because, the monologue, Lorne didn’t want him to do the monologue. Did you contribute to any of Norm’s pieces? And what was that energy like? 

I was brought in to give Norm advice on the monologue, I mean, just by Norm. And two things that stick out that I remember. I don’t remember writing any of it off hand, but I do remember thinking that joke was really funny, the one that everybody got angry about, which was that, you know, why are they having me back if I wasn’t funny? And oh, it must be because now the show’s really bad. So I’m funny in comparison. I think that was the crux of the joke. And, you know, I thought it was really funny. I certainly didn’t discourage him from doing it. But Norm went out there and people, there were a couple of people. I’m not going to mention them, that were very upset by that joke. 

The writers, there were writers out there that booed him. There were like about three or four. 

I don’t. Well, they. Yes, I don’t know. It was writers who did that. I never heard. 

I can tell you at least one. at least one person that it was. No, there were people that were really upset. I mean, I– – 

Can you name the names? 

You guys would always make fun of the show back in the 80s and early 90s. 

F*cking relentlessly we would make fun of the show. We would even, you know, I mean, look, I wrote the cliffhanger sketch in 1986 as a young novice. And I always felt like, you wanna, if the show’s having any kind of, of you know, if there’s any issue that’s an elephant in the room, you might as well go for it. And in this case, the elephant in the room was that Norm was fired in a really awkward manner. And he had every right to come back and throw a dig at the show just for sport. I mean, you know, it was crazy when you think about it. And it wasn’t like, you know, everybody was upset and hurt and like nobody was remembering, like, “Think about what happened to Norm.” I mean, to be displaced in the middle of a season and like, you know, and having to stay on the show and watch someone else take his place, the only thing you can do is to stay on the show. update. And here, everybody was so sensitive about just a gentle poke that was coming from Norm Macdonald of all people. So, you’ve got to take it with a grain of salt anyway. 

You could feel that tension backstage a little bit? 

No, one writer came up to me and said, “Thanks a lot.” 

I can’t believe that they had that reaction. 

Another writer openly, you know. yelled at me like, you know, why would you encourage him to do that joke? And I was like..

I want to mention two things. One, Andy Breckman, who they brought over who worked on, I believe some of the monologue, he was over there. He was a guest writer all the time. And after the Norm episode, he was never asked to come back again. And he wrote some really famous pieces. 

I don’t remember that. But Andy, well, there was a… Andy talked about it in the SNL book, that he that there was this weird tension that he felt when he went back to the show once Downey was gone. And there was a whole new bunch of people there. And we all felt it a little bit. You know, there were certain people who were always super encouraging about my cartoons, like Amy Poehler and Colin Quinn. But there was, you know, there would always be, there were some people who Lorne told me openly resented that I had like a guaranteed slot on the show, you know, as he put it. And he was like, “And I tell them, you’ve earned it.” But it’s not like I was putting on bad sh*t. At the time my cartoons were getting, you know, very encouraging comments from the press and from fans. So it was a strange time back then. And I think there was a level of insecurity among that group that, you know, bubbled over when Norm did that. I also did a cartoon. I did a cartoon that made fun of the show, but made fun of the show and Howard Stern equally when he was like ripping into the “Goat Boy” sketch, he did a whole thing about, because he competed with us for a year or two, unsuccessfully, on CBS, and he launched into a whole tirade against the show, and I did a cartoon about that, and Lorne was happy with it because he said it made as much fun of Howard Stern as it did of the show or whatever, at both sides. I think Howard was more upset with it than the show was.

A Saturday Night Live writer told me the story. This is “TV Fun House.” This is March 25th of 2003 Salma Hayek is hosting and this was the “Fun House”: It was “Are You Hot?” which was you, Chris Parnell and Doug Dale doing the voices. And Lorenzo Lamas had this terrible show, a reality type show called Are You Hot? where he would judge people and have a laser beam type thing where he would like point out people’s pluses. So you do this sketch. 

Yeah. And so we were doing it with cartoon characters. 

Yeah. Are You Hot? And they would have cartoons. 

Sexist. And yeah. 

So this is what the writer told me. He said after dress he went up to you, and, I mean, it killed… he thought it was it was like, so funny. And then he mentioned that Optimus Prime voice was just a little bit off, but it was great. Not really thinking you would do anything about this. And he told me that you freaked out and you sent, I don’t know if you personally or somebody went down to Kim’s Video, which is miles away. I mean, to get a tape of Optimus Prime.  So, is this true and how much time do you have to make this correction? 

I don’t remember that at all, but it’s possible. It’s certainly something I would have done if I could have done it. 

He told me you did. 

I did do it, and so the voice was different on air? 

Yeah! So did that happen sometimes that almost up until air that you were still working? 

Oh yeah, now, there was one time… 

On the cartoons? Wow. 

On the cartoon. Well, there was one disastrous time. And I talked about this in the SNL book, where I did a cartoon about the Christian Coalition network. I had done this a couple of times as a running thing. And this particular night, it was a series of cartoons, like there was a cartoon about Darwin being a bumbling idiot and a cartoon called the Celebots, which were robots that were celibate. And there was a third cartoon called “The 700 Gang” and it was Pat Robertson and a bunch of kids and he was spouting off a lot of nonsensical dogma. And this piece did well. The thing that killed the very hardest was the Pat Robertson group. And they were stuck for a cold open. And Higgins said, “Why not just take that out of Smigel’s piece and make it a cold open?” So I was like, okay, I’m gonna have to re -edit it and give him a life from New York at Saturday night kind of thing. And so I run to back to, and again, I had to go to Sony Studios, which is where we always mix the show and edit it. And so that was on 54th and 10th and it’s Saturday night and there’s always traffic so I bolted down there. Got it done, re-edit it. I had to re-edit both cartoons, you know. Got it done by about 11 o ‘clock and as he’s laying down the sound, something’s wrong. Something crashes. I don’t I still don’t know exactly what happened, but there was no sound and he had to do it again and now I’m freaking out. And I run over there. Literally at like nine eleven twenty five. I get there, and Ken Aymong, the supervising producer of the show, on his own because–he knew I was up against it–he had created a version. He had them chop a version on their own with room for someone to say “Live from New York it’s Saturday Night” — live. And that was going to be, Darrell Hammond was in the booth ready to do it. So I get there finally, and he says, “I’m sorry, I’ve got no time to ingest this video.” But thank God he had done that. So I run into the booth, because I had done the Pat Robertson voice, so to make it consistent, it made sense for me to do it, to say “Live from New York it’s Saturday Night” instead of Darrell. So I run into the booth and Darrell takes his headphones off and hands them to me. This is halfway through the sketch. And I say “Live from New York it’s Saturday Night” for the first time in my life, like writers don’t get to say “Live from New York.” This was like, could have been really fun for me under a normal circumstance, but instead it was this horrendously panicked moment that we just got through by the skin of our teeth and I said it, the sketch ended, and I walked out of the booth and I saw Lorne and I just shook my head like, “I’m sorry, I’m so sorry  that I caused all this stress,” you know, because I could have, yes, the whole thing crashed at 11 o ‘clock and caused all the disaster, but I could have maybe been a little less picky as I was editing the piece, got it done more like in the 10:30 range.

So he wasn’t thrilled with how it all went?

No, he was fine with how it went but it was all this stress that..

The behind the scenes stress, yeah. 

Didn’t need to happen. I felt so bad. I felt so terrible for, you know, ’cause I felt like I’s almost broken the show. But thank goodness Ken Aymong had the presence of mind to..

Yeah, he’s a really nice man. He supported my other podcast and we’ve had lunch and stuff.

He’s a comedy geek too, which is a lot. of fun. Just loved the show and loves comedy and is a real student of it. So that always made it, you know, he really supported the writers all the way through the– 

Yeah, he’s such a nice guy. I wanted to talk about you and Sandler collaborating, ’cause people know the movies and stuff, but you and him wrote some really funny stuff. Like, my personal favorite that I know that you guys wrote was that French class. Alec Baldwin was host and it wasn’t until like I think after “Update”–normally the strongest stuff, they put first But that actually that show was jam-packed. It was the Chris Farley show with McCartney, but that French class was you and Sandler, right? 

You know, sometimes I don’t remember the people I collaborate with. If it was my idea that was an idea I had based on you know, I took high school French and it was just a joke about the way people have strange inflections when they are learning French. And, but I wouldn’t surprise me that Adam helped me with it, no doubt about it. He helped me with a lot of sketches. The “Pinky Ring” sketch on the Joe Pesci show, I’m pretty sure Adam was the only other writer who helped me with that one. 

I wanted to ask you about the Joe Pesci show because there are only so many slots for writers. And that Pesci show in particular, I think that they only had like seven or eight sketches and you got two of them on. You wrote “Pinky Ring,” and then you also wrote “Bensonhurst Dating Game” with Sandler, I believe. 

I think I had three on because I think. –

Okay, but you get three on… 

Wasn’t there a sketch? The robbers are watching TV and…  

The crooks. I’m a happy dogger that was, like a commercial… 

Yeah, yeah, and it was just a play on the trope that every time you turn on the TV, the actual thing you need to see is on right at that moment. So it was a what if you have to sit through commercials. 

How hard was that for you in the office knowing that you had three out of, I think, nine sketches? There’s– nine slots and you got three on. Is that, behind the scenes, do you hear people complaining? I mean, what was that like for you? 

The writers were really, I mean, everybody, it was all, you’re thrown into a place of competition, which makes the show, you know, harder to deal with emotionally than it would be if it was a calmer scenario where it’s not, you know, every show has to be, you know, you always feel like you’re, it’s do or die because you’re only going to have this host for this week. It’s not like SCTV where, oh, we can use that sketch anytime, you know, a lot of times stuff  is host-dependent.

What was your record on getting sketches on for one episode? I mean, Pesci was three. Do you, do you know? 

I don’t know, but I mean, probably like… three or four, I guess, I did it multiple times and the Pesci show was one of those where, I’m not sure, I feel like, I know that “Pinky Ring” and “The Robbers” were my idea. I think “Bensonhurst Dating Game” might’ve been Adam’s or something. 

I thought it was the two of you, but I could be off. It was a long time ago. 

I only wrote it with him, but yeah, I, honestly, there weren’t as many writers back then and we had worked with each other for many years and we’re all friends. And I feel unless you know, I felt like it was a much more supportive environment at the time.

A lot changed over the years. I know I’ve heard it’s really good now.

I remember publicly someone saying, openly saying [they] would not laugh at read-through at other people’s sketches, which…

He did say that he was in the A&E documentary and was interviewed and said that he said that. 

Yeah, I was like, I can’t imagine not laughing because like we all wanted the show to be good, you know, and we were all rooting for sketches to be good. We would, what we would root against was a, what we perceived as a bad sketch getting into the show. That’s what would upset us. If we thought something was either hacky or something was just not going to work, then we would be bummed. But we would never be bummed if a funny sketch got into the show that we didn’t write. We’d be excited. 

I wanted to ask you because I heard one of the sketches the writers didn’t like because maybe it was perceived as hacky was The Sweeney Sisters, because there weren’t a lot of real jokes. It was more, you know. just the character stuff without the writing, which really didn’t happen a lot with you. 

I love The Sweeney Sisters. 

I mean, they’re so funny. I just thought from a writer’s standpoint, I wasn’t sure. I heard that the writers didn’t like that. 

I think it’s easy to label something as hacky if it’s so performance-oriented, but those medleys were so carefully crafted and so silly. It’s one of those, either like that kind of music and and and like what they’re parodying, or you don’t. And if you do as I did, then you really admire the way they would segue from one [song] to another and you enjoyed, you know, the superciliousness or sanctimoniousness of Jan Hooks’ character. You know, I was a snobby writer in a lot of ways, but I loved performers and I loved watching them be funny as long as it had some intelligence to it, and I thought that sketch did. You know, the only criticism you could have made about that sketch was that it was, “Oh, they’re ripping off Bill Murray’s lounge singer,” but they took it to a different level because they were making, doing this medley thing. 

It never occurred to me, but I see that now. I was convinced 100% that that Steve Martin “Holiday Wish” sketch, which made the “Best of” Christmas special, where he’s talking into the camera “if I only had this many wishes” and it starts like world peace and then it gets completely ridiculously selfish. It was such a Steve Martin–I was convinced Steve wrote it himself because it is so Steve Martin, then I found out you wrote it. 

(laughs) Well. is like one of my career highlights because I remember Steve Martin saying, it’s very rare that I get something written for me that sounds like me that, I mean, it was such a thrill. And it was an idea I’d had in Chicago, sort of like “Not Gonna Phone It in Tonight.” I remember driving on Lakeshore Drive and talking to Michelle. Michelle and like, what about, what if I just, if I had one wish and then I started riffing on it, but I had no place for it. And again, it wasn’t until Steve Martin hosted and it happened to be near the holidays. So I went for it and Bob Odenkirk threw in a great joke, and Steve actually, you know, it did great at read through, but then I got to sit with Steve and he tinkered with it, made the ending funnier. So he ended up writing some of it as well. But yeah, that’s absolutely a career highlight. 

It’s a five star sketch.

He’s well, however good it is or not, just the fact that he enjoyed it and it did well and that it’s Steve Martin, who’s one of, you know, at the very top of my heroes of comedy. 

What was your reaction to that New York Magazine piece by Chris Smith about SNL being a grim joke This was March of ‘95, because it was before the internet It’ll be 30 years next year because internally they were so upset. 

I sat with Chris for a long time and I tried to get the point out that, you know, it was a very difficult year. It was a big challenge because they had lost, I mean. Well, you started saying that they lost they had lost Handy, and me, and Zander and the Turners. That’s a lot of writers to lose in one year when your writing staff is only like 14 people in the first…

I want to interject real quick that Jim Downey said a quote something like that 90% of the people that did our writing that got on the show left our show. So, I mean, he exaggerated that number a little bit, but..

It was a little high, but it was definitely a large amount. And then they’d also lost Dana Carvey. You know, we lost him for the very last half of ’93, of the ’92-’93 season, but this is like a full season without him. And they didn’t bring in anyone really to… or I don’t know, was that the year they brought in Michael McKean? This is the McKean/Garofolo…

They brought him in that March, the Helen Hunt episode. That was, yeah, that was ’93 to ’94 in the winter. 

Oh, right. I get those years confused, yeah. This is after ’94, ’95, and they’d already brought in the Janeane year and all that. 

Yeah. That was the ’94 to ’95 was Janeane [and Laura] Kightinger 

Right. So it’s already a year since we’d lost Handy, and me, and Zander and the Turners, but you know, again it’s like, I tried to emphasize that to him, that, you know, this was not about some kind of culture that needed to be torn down and you know, it’s not about “the Lornenettes” or whatever, you know, whatever quirks about the show that he wanted to highlight as problematic. It wasn’t, because nothing had changed in terms of the institutional running of the show from 92 to 93 to 93 to 95. Nothing, it was the same thing. The only difference was the show’s always gonna be as good or as bad as it is because of… that core–the writers and the performers, and you’ve got to have the right mix of both, and they didn’t.

Yeah, they didn’t gel 94 to 95 and 93-94.

And that’s all it was. It was a bad mix. It would have worked itself out, but you know, so yes, it was absolutely a hit piece because reasonable people I’m sure he talked to Downey about this, and I emphasized  it. I said, “Hey man, the Chicago Bulls won three championships and then Horace Grant left. And they couldn’t get past, so even when Michael Jordan came back, they couldn’t get past, you know, they couldn’t even get to the finals. You just need one major piece to go and you’re going to need to replace it.” And but, you know, so I feel like yeah, he definitely had an agenda and so I did, I was frustrated by the piece. 

People internally were so upset. I talked to one producer and he’s like, there’s things that aren’t true. The one thing I know is not true is they talked about Ellen Cleghorne in the premiere that was Steve Martin/Clapton, she had one role as a prostitute, which, she was in “Buh Bye” They did the second time, the only [other]  time they did “Buh Bye.” So there were definitely things in that article that weren’t accurate, but I was told the show still has issues with that article, and they are just wary of journalists up to this day. I mean, it did have a big impact on the show. 

Because that guy was embedded into the show. He earned the trust of all these people, hung out, laughed with everybody, and then painted this picture that came from a very specific… agenda.

I could go through that year There were good sketches: Sandler’s Hanukkah song, which.. 

Of course there were good sketches. Every year… 

The Japanese game show Andy Breckman’s Japanese game show with Alec Baldwin.

You know, I could point out good sketches in the Jean Doumanian year. You know, the show is always going to be up and down. It’s just a question of the percentage of up against down, you know. And also what stands out and I always say this when I talk about the first few months of Conan, people remember the stuff that really tanks, because there’s so much mediocrity on television there’s a little bit of great stuff, a lot of mediocrity, and then there’s some real sh*t. And so you remember the great, and you remember the sh*t, and if a show, Conan we would have some complete train wrecks every now and then those first few months. We also created a bunch of sketches that ended up being staples of the show for 15 years But there were a couple of train wrecks and people remember that stuff. 

I will say this about Saturday Night Live during those two years They weren’t letting standbys in almost ever which now they let 75 or 80 in for live. And it’s that’s why sketches don’t bomb anymore, and I think if that would have been the case back, 

I didn’t know that was the case. That they let that many standbys into the live show. 

Oh, yeah, because they’re so they’re so careful about the audience. That is the biggest difference with the audience is why sketches don’t bomb is because the standbys and also at the top of the cold open, which never happened with you, they hit the applause sign right at the top of the cold open to get that energy from the audience. I’m telling you, it’s so simple. but those two things. I mean, when do sketches bomb? 

Well, I mean, I totally agree about the standby thing, because we always were frustrated that a lot of times the air audience was worse than the dress audience. 

They were all VIPs sometimes, almost all, and it ruined shows. 

Yeah, there was a lot of VIPs, a very jaded kind of thing going. So that’s nice to hear, although sometimes I think the audience just likes screaming nowadays. 

I know we have to go. So I want to ask you two things. First of all, Leo on Netflix made my wife cry. We were laughing and she just, I mean, lost it. I mean, it was, and to get you guys such a good score and rotten tomatoes for a comedy. I mean, it was comedy plus a lot of those drama. You totally scored. 

I was very happy with that, especially the 91% audience score on Rotten Tomatoes. 

That was, yeah, I mean, everyone check out Leo on Netflix. And then the second thing, and I laughed the entire time was the, your sketch fest in San Francisco special Let’s Make a Poop, which is on your YouTube channel, which is [named] Triumph the Insult Comic Dog HQ. How dis you put this together this? I mean, you’re roasting “Weird Al” Yankovic, you have Rob Schneider, Amber Ruffin, Michael Winslow. you do a Jeopardy parody, and then you have this touching ending, which I did not expect with your friend Richard, the Black Wolf Dragon Master from the Conan remotes. How hard was this to put together? I mean, it turned out amazing. 

Well, you know, we had done a few of these before, not many, but we’d done a few of these game shows before. And Jeremy Schaftel had created this Jeopardy board kind of thing, and he always operates it. And so it became something where the game show, even though it looks complicated, we sort of established a template and then it’s just a matter of writing the jokes. You know, and I don’t, obviously, and I always try to emphasize this. I don’t write Triumph by myself. I have great writers helping me, ’cause it’s just too much. 

That’s what I was gonna ask if you had other…

If I had that level of, I’d be Robin Williams or I’d be a lot richer. I wouldn’t be in my basement. I would be, you know, on top of a very tall pedestal talking to you and I would tell you I only had five minutes if I were that funny. I still can improvise and I can still you know, I did a Triumph thing at the Trump rally the other day of the Trump trial. 

I saw.

You know, and I got to improvise some funny stuff there. But I also had great jokes that writers helped me with a lot of them, most of them. And so yeah, it’s, it’s not that hard when you create something that’s just, you know, just all we got to do is put the jokes in now, you know, so we write a monologue together and then we, we write jokes for the game show and that’s most of it. 

The “Weird Al” Yankovic songs were something that I’d written with Craig Rowin who wrote for “Night of Too Many Stars” because we thought we were going to do something with Al Yankovic 10 years ago or 9 years ago and we’d already written a lot of those song parodies, so. 

“I needed to laugh.” These are YouTube comments. “First time watcher of this perfect show. Smigel, you freaking are an amazing genius.” “Funniest 63 minutes I’ve spent on YouTube.” “I’d like this a thousand times if I could.” “This made my week.” I can’t emphasize how funny that was. And I know you have to go. I got to two pages out of like six that I wanted to ask you. And I know that you’re 

I’ll come back. Is it possible in like six or eight months we could do another one? 

Uh, yeah, sooner because I’ll be less busy. You’re okay to do it sooner? Yeah, because I’m less busy right now. I’m going to probably get into another big project fairly soon. 

Okay. I’ll do sooner.

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