Inside Late Night with Mark Malkoff - Inside Late Night: Ian Maxtone-Graham

Episode Date: October 13, 2026

Veteran comedy writer Ian Maxtone-Graham joins Mark Malkoff to look back on his years at Saturday Night Live, from breaking in with help from Jack Handey to helping shape Norm Macdonald’s "Weekend Update." He also shares stories about Adam Sandler, Chris Farley, Phil Hartman, Al Franken, and some of the sketches that defined his time at the show.

from late-nighter.com, it's Inside Late Night with Mark Malkoff. Welcome to Inside Late Night with Mark Malkoff for Late Nighter. Today, Ian Maxstone Graham talks about his years writing for Saturday Night Live. Ian McStone, Graham, thanks for talking with us. I'm very happy to be here, always happy to bloviate about my time at SNL, which was a wonderful... Amazing time. I was honored to be there with those people. You grew up in New York City. Did you watch the show? Did you ever attend the show or try to?

I attended it once. I think Conan got me tickets, and it was a very good show. It was the one where Patrick Swayze and Chris Farley did the Chippendales, did the Chippendales striptees dance. And so I was there live for that. And I always felt great to have seen that, but also terrible because I believe I asked Conan for two tickets. And then I didn't realize how hard it was to get tickets. And then I had two more friends. So I asked him for four tickets. Now, four tickets for air. Like, that is a hard ask. So I still feel guilty about it.

But my gosh, what an episode I got to see. Yeah, Dirty Square Dancing was the Open. It was a really, really, they did Hans and Franz. It was really strong. Did you have any inkling or ambition to write for the show? Because you were there about a year or so later. Did you have any idea at that point? I don't think there's a comedy writer or even mildly funny person alive who doesn't have an ambition to write for or maybe perform on that show.

I mean, yeah, through high school, through college, I mean, yeah, right from the beginning, watching it with my parents, watching Chevy Chase. I'm Chevy Chase and you're not. He had that magical kind of smirk, that thing that just set the tone for update in such a great way. And then, you know, Dan and Jane and Dennis, I mean, everybody on that was great. And then, of course, everyone else, John Belushi. I mean, I'm not going to list the people who have been on Saturday Night Live, but who would not want to join them in one way. I worked selling wine in New York for one holiday season. I was a temporary hire at Sherry Lehman and Chevy Chase came in and like, oh my God.

Like, who doesn't want to go and wait? So I go up and I say, are you being helped? And he says, constantly. So he was clever and funny and in my face right away. It was perfect. I love hearing that. So I have to ask. So you were right.

at one point for not necessarily the news. At the same time, are you writing for Army Man, which is a newsletter for comedy writers? And that's basically how you got on Jack Handy's radar, correct? But were you doing both at the same time? No. Army Man was when I was mostly unemployed, doing a lot of spec writing, which turned out to pay off well for me, but spec writing of things that were never being sold, just sitting and writing, living in the Hollywood Hills with a bunch of writers and very funny people who would be great friends and part of my life. And Army Man showed up from George, who I'd met a little bit. George Meyer.

George Meyer. And, you know, he was doing it, I think, in Boulder with a selectric and scotch tape and a, and like a razor blade. Like, that's how things were put together back then. and I remember seeing it and just saying this is the funniest stuff ever and could I possibly, it was just like SNL, could I be among these comedy gods who are writing for this? And then I submitted some stuff to him, and I remember when the next issue came to the house,

I could read through the white envelope. He said everything to people, you know, first class mail. There was nothing. Nothing cost effective about this. And I remember reading through the clear, not the clear, I remember reading through the white envelope, one of my jokes.

And it's like, okay, man, I'm an Army man. I love that because you were writing for HBO, but this is, I guess, more prestigious. This is later. Well, to me, I mean,

listen, that was my first comedy job. I'm deeply grateful for, you know, Billy Kimball, Pat Lee, John Moffitt, people who got me that job. You know, I was there with Mike Reese and Al Jean, who obviously I'd work with and be friends with for decades and decades. You know, I'm not going to list all the writers, but it was a great place to be. I was thrilled to be there. And then Army Man was like, it was another thing.

It was like, I'm here with the sort of royalty of comedy, Jack Handy, John Swartzweiler, this guy Jim Wheat, who showed up in episode and issue number of three, I think, who is just an idiot savant of comedy. He's no longer with us. But my God, Jim Wheat, I could do a whole podcast about Jim Wheat. People should look him up. I was able to publish him later in National Lampoon, which made me incredibly happy. How soon that you're writing now for Army Man, did you realize that Jack Handy was a fan of your work? Was it very quickly that he reached out to you? No. I will tell you the whole story and apologies to you and your listeners and your editors that it's long. But it was sort of a circuitous route.

So I'm living in the Hollywood Hills. I'm teaching SAT prep, which I have to say I love doing. I love teaching those kids SAT prep. I had to quit the job because I liked it too much. And I was making what for me felt like too much money, so I wasn't writing enough. But I was living in this house full of these amazing writers, including, I mean, Kevin Jarre, J-A-R-R-E, look. guy up. What a mentor. You know, Ron Richards, John Viti was there for a while, David Sacks,

Roblo Zabnick. Anyway, and I'm just writing, and I'm writing these prose pieces, long prose pieces, with nowhere to send them. National Ampoon was not in a great place right then as far as being strong editorially, I think. I'd never thought of something to them. So I was literally sitting his little tiny basement office where I was actually sleeping. There's a little office downstairs in this crowded house and writing these pieces for nobody and for no reason. And then I go to New York to work on this game show called Clash created by Tim Disney and Billy Kimball. And they hired me to be the sort of producer headwriter. And that lasts a while, and it's a great experience.

It's my first experience running a show, or running the comedy anyway, of a show. And I got to meet Oakley and Weinstein, who would later hire me at The Simpsons. So that was, everything about that was great. But then that ends, and I'm unemployed, and I have all these pieces, and I know there's some new editors there at National Ampoon, and I just think, what the hell? And I put them in envelopes and send them in. I think to Sam Johnson and they start buying them

and they buy kind of all of them and these are things from my drawer I mean this is the old days where it's not like sitting on the cloud is like pull out the piece of paper from the drawer, read it over, put it an envelope, put a stamp on it and then they said you want to be a contributing editor and I said of course I do it's National Lampoon and I came in and met them and George Barkin

And then they hired Larry Doyle, who I'd known from earlier. He was incredibly funny guy, like an award-winning comedy writer, Mark Twain or Thurber, one of those awards. Super, super funny New Yorker and other things writer. And then they make me a contributing editor and they make me a full editor. And one of the things that we do, and I told you this would be long. No, I want to know. I'll go step by step. So one of the things that we do is we want to reach out.

to Ian Frazier because we were all giant fans of Ian Frazier and there had been a little it was not a scandal Ian Frazier had written something about Coyote versus Acme

which was the same idea as something this guy Joey Green had written I think maybe for National Ampoon now there is no way in the world that Ian Frazier is a plagiarist he's one of the funniest humans

on the planet and also one of the sweetest decentest guys he doesn't sit around trolling through nat land for something to steal to sell to the new yorker it was a coincidence and it's a great idea and both pieces were great but there had been some sort of funny sort of back and forth with him about that and we just wanted to like sort of tell them what fans we were and take him out to lunch so sam and chris marshal maybe larry at that point i don't know maybe maybe George Barkin, we took him out to lunch and he was so nice to us. And what a wonderful guy. And I said to him at that lunch, hey, can you give me Jack Handy's phone number? Because I was by then in charge of the front of the magazine, all the little short pieces. I want him, Jack Handy, to sell us some deep thoughts. In the past, he had sold them to Natlamp. It might have been the first place they were published. They were also published. in Army Man, but that lamp paid, and we were super happy to have them after they'd been on

SNL. Any association with that comedy genius with deep thoughts was great. And again, we had a history with deep thoughts. So I got his number. I called him up. It was the old days where people would answer their phones. And I said, hey, will you sell us some of these, some of your deep thoughts when they've been on the show?

And he said, yeah, sure, that sounds great. Super nice, super friendly about it. And I think probably, to get back to your question from two or three hours ago, probably maybe he took my call and talked to me slightly because he'd read my stuff in Armyman. So I don't know that for sure. He might have known to anybody. It's like, yeah, National Lampoon. Sure. But maybe it was maybe the Armyman helped me get my call taken seriously. And right then and there, did he invite you to submit to Saturday Night Live for sketches to send in? He did not. He did not. Nor was I going to ask him because this was just me saying, please sell us your stuff. I want your stuff. I would not, frankly, I didn't like bugging people for jobs. And I wasn't going to bug a stranger for a job of all people. And like, hey, we want to buy

yourself. Oh, by the way, like, of course you want to write for SNL. Find a person who doesn't, right? there's probably neuroscientists and, you know, rocket scientists who would like to write for SNL. It's not a secret, you know? So, no, I didn't mention it. It was just, please send us these. And then cut to, I don't know, a few months later, I love the job at Nat Lab. I could still be there if they had not laid me off.

But money was tight. We didn't have a ton of ads, didn't have a great circulation. So in the middle of I thought making the magazine better and better, working with these great editors, co-editors of mine, Dan O'Keefe, I then worked with, Envipe was on there. We had like a great group. In the midst of all that, they ran out of money and they led off me and Larry Doyle. And it wasn't like an angry firing. It was just, you know, we don't have the money. You guys are the most recent hires, so we were gone.

And I found that. out when I arrived at work and everyone was nice about it. Everyone came into my office. You can keep your office. You can stay here. You can be a contributing editor, but you're not going to get a salary anymore. You won't be a full editor anymore. So this was heartbreaking, of course, because I wanted to be there with those guys putting that magazine out like forever. I was, I love that job. But this was it. Jim Jim Maro was the CEO and owner, and he laid us off. And one of the things I had to do was call Jack and say, listen, don't bother sending me this stuff because I'm not here anymore. Now, we could have sent it to the other guys, but I felt like the magazine was diminishing,

and I didn't feel like I could guarantee to Jack that I would take care of the stuff, of the, of the deep thoughts. But again, no disrespect to the editors who remained still good friends of mine, but I just said, you know, don't bother sending. And he was super nice about it. And then I hang up. Now, it is 15 or 20 minutes later, the phone in my office rings. And at this point, having never dropped any hints, I honestly don't think I had an ulterior motive when I called them up and said I'm not working anymore. Maybe I did. Maybe I secretly was scheming all along.

But out of the blue, I get this call. The phone rings and I have a sense of who it is. And Debbie the receptionist says, Ian, you got a call. It's Jack Handy. And I pick up the phone and say, hi, what's up? And he says, well, maybe you should apply to SNL since you're not going to be at Nail lamp anymore. And I say, of course, of course. And I say, well, can I, you know, have like a few months to write some sketches? And he says, no, try to take like a couple of weeks because we have an

opening now. So no pressure, right? This was midseason. This was 1992. It was the 91 to 92 season. So you had a few weeks to write four sketches, was it? Incorrect. Okay, great. Tell me. Incorrect. Please. It actually stretched out longer.

It was the fall of 91. Oh, wow. Okay. It was the fall of 91 when I was laid off. And I had two weeks. You know, it's hurry up and wait, right? I had two weeks. I took one prose piece that I had been going to sell to that lamp and I turned it into a sketch.

I wrote three other pieces. and I sent them in one copy, you know, everything's mail back then, obviously, one copy to Jack, one copy to Jim Downey, who I had met a couple times and was certainly my comedy hero. I felt like I could sense Downey's influence in many sketches in the show,

whether he wrote them or was just the producer slash head writer for them. So I felt like I knew Jim's sensibility just from a distance, and I sent these sketches in and I heard basically nothing. I think Jack may have said, yeah, they got them, but they're not hiring anybody for a while. That was, let's say, November.

In May or maybe April, whenever it was the end of the season, close to the end of the season, it's now spring 92. I get a call on my answering machine, obviously no cell phones then from, or no cell phones that aren't the size of, you know, to phone books, I get a call on my

answering machine. I remember I'm at the library doing research, and I call up and I get this message, and it's from Evie Murray. And the interesting thing was that Evie Murray, on top of being a wonderful person who was a great ally when I was at the show, was actually the person to whom I had sent some sketches back in the Ebersole Tishler days when she had been an assistant on the show. So I knew the name.

I didn't know she was still there. And Evie says, Lauren wants to meet with you. And what that means, I don't know if Lauren had read my sketches, but it meant that certainly it meant that Jim had read them. And I went in and met with Lauren. And it was the night of a show

when he met in his office, it was the 8-H office so I was actually on the ninth floor is a sort of balcony office and we talked briefly not about anything particularly relevant to my sketches I think they sort of

maybe want to see if you're you know play well with the other kids and then a couple days later I get a call from Rob Schneider saying hey man I read your stuff I'm so glad you're being hired here let's work together and then I got a little later from the show itself saying,

yeah, you're hired. Like some sort of impudent idiot, I went and crashed the rap party because it was a show night. And I think I went and sat next to Lauren and Sharon Stone. I have to correct me, but I think it was the fourth, the last show. I don't know why I had the nerve to crash the party and go and sit next to the host and Lauren. But I think I felt welcome there because, Rob had been so nice and Lauren had been so nice

and I was I just couldn't wait to be around those people you know I couldn't wait to get there I wanted to talk about the packet we talked years ago I remember you telling me one of the four sketches that you wrote actually got into the show it was a World War II piece and it was Mike Myers in bed

and Miranda Richardson was the host and it was three-legged Hitler right wasn't that Rob Schneider that was in your packet as three-legged Hitler you know obviously Mike Myers does great English accents. And it was, you know, that was close to as I wrote it, which is not always the case.

And getting your packet sample sketches in on the show is not always the case. That's what I've been told, yeah. And, you know, it basically waited until you had the right host for it, which was Miranda Richardson, who was, you know, fantastic. She had absolutely the look and the skills for that role. And Mike was great. And, you know, Schneider was three-legged Hitler was, I mean, I could not have been happier. And I, for years until it burned down, I had a picture of all of them on the set from that show night or

or from dress maybe. And it was, it was great to have right over my desk. The sketch did really well. Unfortunately, with music rights, I don't believe it's online, like a lot of great sketches back then. They don't want to pay the music, so it's not on, unfortunately. So the music is the music cues? Because it was, it was Bluebirds over the White Cliffs of Dover, has to be public domain, right? I'm not sure. Maybe it is online now. The last time I checked a year or two ago, it wasn't, but I hope so. But it did very well, I remember.

So that was in your packet. Please continue. And then the other one you mentioned was like a sports announcers. They're like, oh, you hate when that happens. Yeah. Well, when did we talk? A long time ago, there's something wrong with me. We talked, oh, it was like, it was like 20 years ago.

You were very nice to me on the phone answering my nerdy questions. and I just kind of have I can remember things like this. Well, you're ideally suited to your job as a writer and podcaster. Okay, yeah, it was, it was just, it was a very, very thin idea, but it made me laugh. And I sort of felt it might be up the shows and Jim's Alley, which was sports announcers saying about good sportsmanship, usually, not about who wins or loses. You like to see that. or when something just kind of ugly happens,

oh, you hate to see that. And it was them trying to decide and then you sort of set it up with some, you know, some, oh, he's patting him on the back. You know, he's helping him up, petting him on the back. You like to see that. Oh, he's putting a kick me sign on his back. Oh, you hate to see that.

Yeah, did you keep your sketches short? Did you know that that was a thing at that point? You want to keep them short when you submit? I think I probably did. You know, to me like, Eight was a good number. 11 was kind of the max in terms of pages. But I think that one might have been eight pages.

And eight was a, it was tight and short. And I think like, make your premise, do some twists, have an ending, and you're done. Yeah.

Sometimes they would get long because they were sort of chasing the blow, you know? And that one, I don't remember how it ended, but I felt like it didn't want to overstay its eight page identity. Was your first, show then officially when Jerry Seinfeld

hosted that you were there and you were a writer? Okay, you probably have this, maybe you have this memorized. So this is who we had at the, I had a three show, I had a three episode pickup. Like that was my job. That was my contract.

Three episodes, tryout period. The last three episodes of spring 92, so the 91-92 season. It was Seinfeld, it was Tom Hanks. Tom Hanks. Woody Harald. Like, okay, three comedy gods, obviously, three, I mean, what can you say?

Three legends. And Seinfeld came in with Larry David and Larry Charles as writers. And Smigel, I think maybe with Seinfeld's help, I don't know. Seinfeld might have worked on it with him. And maybe Larry David and Larry Charles did too. and I think Sandler may have worked on it with him. I don't remember the initials on that sketch, but it was called Stand Up and Win.

It was a game show based on being stand-ups. And, oh my God, it was so funny. And that was when I was really exposed to how incredibly funny Smigel was and how great he was at writing for a host and his knowledge of the stand-up tropes. Sandler as a cast member and I'm sure writer fitting in so perfectly. Obviously, Seinfeld, one of the legendary stand-ups,

like that felt like the platonic conception of how to write for a host and how to write a great sketch. And honestly, with that and with the two Larrys there, and seeing that destroy, utterly destroy early on in the, in the table read, I felt like, I don't know, man, I was at training camp for the, for the Patriots. I had walked on from a high school team. I mean, the quality of that writing talent and the quality of what was being read there blew me away. My sketches that I submitted did okay. I did submit, I think, fetal abuse laugh athon, but it didn't get in. It did okay,

laughs-wise, but my God, that table read blew me away. It was really strong. I do want to mention, you did work on the Clinton-Jerry Brown debate, which was a cold open. It was you, Jack Handy, and Rob Schneider. I remember you telling me you pitched a joke, and Jack Handy, it was a good joke, and Jack Handy said, you know what, that's a little sweaty. This is your first week. Okay, you have a bizarrely photographic memory. This was a great, edge-year-old. educational moment for me as a writer. And I really, I've kept it to this day, which is, I mean, there's a lot of things, you know, a lot of things I could tell you that I've learned as a writer. But this was a very good one, which is, when you pitch something, if nobody laughs, it's not a matter of poor hearing or acoustics in the room.

it's not a matter probably of not having been loud enough although that can happen but it isn't don't assume any of those things assume it is because it wasn't funny enough for anyone to laugh and no one's being mean good writers don't shoot stuff down they just keep pitching right because most things aren't going to get in right so so it's it's not a great room runner who stomps on stuff that's bad you want to encourage people to keep pitching, you just don't respond. So I repitched it.

And at that point, Jack, in the sweetest way possible, said, nah, you know, I think that's a little sweaty. And first of all, the word sweaty, Jim Brooks's version is eggy, which I think is like egg on your face, but it's like you can feel the joke trying. And so I learned to try to not be sweaty. I also learned don't repitch. They heard you.

And look inside yourself for the next joke. And this is a lesson maybe for comedy writers. And it's a lesson that I have got from being in the room with amazing pitchers, guys like Mike Reese, for instance. Which is believe that there is within you the ability to come up with more funny stuff. And that clinging to the stuff you've already pitched will not free you to find that next thing. Wow. I love hearing that story. I did want to ask you because normally the political cold opens, and this one did so well, it's usually the real estate as Jim Downey and Al Franken normally. Was that highly unusual that Jack Handy and Rob Schneider were working on a cold open without Downey and Franken on the political side? I think it was. I think it was unusual. I didn't know anything then. I just knew, hey, I'm in a room with these two unbelievably hilarious guys and they're being nice to me.

And even when they're being mildly less nice, they're doing it a nice way. So, like, again, much of the time that you're there when you're there for a three-episode tryout is like, I'm here. I've been to the top of the mountain. I might not stay in the top of the mountain, but I'm here with Jack Handy, like this hilarious guy and with copier guy, hilarious copier guy, who also, it turns out, is a really funny writer and a funny sketch player. So, like, yeah, you're just there and you're not thinking like, oh yeah, this is kind of Jim and Al's turf. And it, yeah, played pretty well.

It was, and I think Frank had actually showed up in it as Paul Saundas. He did. He did at the end and it got a huge laugh. Yeah, yeah, he was good. That may have been my idea to cast him there, but I hate to take credit for something 33 years ago. But I, he, him showing up as kind of nerdy Paul Sangas was, I think, a great, a great reveal.

Yeah, it was a really strong sketch. And then the next week, Tom Hanks, you didn't, I don't think, get anything on. And then Woody Harrelson, I knew at this point you were nervous. I have to score. And you got the sketch, the last sketch of the night. But normally a lot of times the energy is really low from the audience. But the sketch did really well. Can you talk about it?

Okay. So first of all, I had put it in the packet with Jerry. Seinfeld and I put it again in the packet with Tom Hanks. I don't know if it was read with Tom Hanks. There were, I think, some personal reasons related to one of the other hosts. It was like maybe something about this particular topic would not be ideal. So, but no one said it isn't funny. And on the one hand, as a new writer, you hate to resubmit something. It's kind of the sketch submission version of repitching, right? But on the other hand, I was encouraged by Jim, and I think by Lauren as well, to resubmit it.

And, and again, I could see all three of those who's been good at it, but Woody obviously could be very good. And Phil as a dad just seemed natural. And Victoria Jackson, as the mom, was, to me, like, utterly perfect as a ditsy pregnant woman. Nothing could be closer to her kind of wheelhouse. and I don't remember I think by then people were a little bit sick of it so it didn't destroy the table read but it did okay and I think Woody liked it

and that's obviously going to make most of the difference and so it got up but it got up toward the end and I think I actually had a little bit to do with all three of those last sketches at the end of the show one of them was maybe Gannon PIPI by the late Dan McGrath, and I was able to work on that with him. You always want to get your initials on

sketches. Like, if it's not your initials first, try to get them in there somewhere. Try to get a joke in there. That was Kevin Neal, and that was a politically incorrect private investigator. They did a few with those. So you worked on this. And then this sketch that we were talking about, the 10 to 1 sketches, they would say, with Woody Harrelson, the fetal abuse laugh aton. Phil Hartman was in that as well. And basically the premise is Phil, I believe it's Phil or might be Mike Myers' his very concerned father. And he leaves. It's Phil, yeah. Phil being a little bit taking from his anal retentive chef,

just like, you know, there's people there who might be smoking, and I don't, you know, just nervous about the slightest danger to fetal health. So you just set up the contrast of this slightly anal overconcerned dad and this underconcerned, very pregnant Victoria Jackson, which already you feel like something's going to go on here, and the perfect wild card to me is Woody. Yes. That one line that he has is,

he has Irish coffee and his logic is the caffeine and the alcohol, they probably cancel each other out. It's fine to drink. Yeah, actually, it was going to be coffee, but if we Irish it up, it will counter out the caffeine. So the sort of idiot logic of that, again, that played nicely.

I was very happy with it. Now, you know my career much better than I do, but maybe I have or haven't told you about the ending of that sketch. I wanted to ask you how that happened with Lovett. Are you talking about the microwave or are you talking about Lovett? Yes. No. Because the microwave was, I guess, was the climactic funny moment of that.

I think it may have ended with her falling down the stairs. I don't remember. Filling down the stairs, I don't remember how we ended it. But it was the mic, once you get the belly in the microwave and you get that microwave sort of fritzing on and off, the light going on and off, and you get her reaching over the back. She's already sniffed the glue.

Like, that was a big laugh, right? The belly in the microwave. So the ending that I wrote was Schneider and Sandler in a big t-shirt playing that child grown up as a two-headed, two-headed baby. Horrible, but, you know, it's a rare occurrence and seem like it sort of fit the sketch to have this is what happened. And they're two heads sticking out of a t-shirt bickering with each other,

and you go out on them bickering. And they're kind of like biting each other on the ear and stuff. Somebody, maybe it was Andrew Brewer, our wonderful, very friendly, nice standards guy, said, we can't do a two-headed baby. And whatever. Andrew Brewer was a great guy to work with. I've never had a more pleasant relationship with a standards and practices guy. So what's our ending?

And I thought, well, let's have a guy with one head who would be funny as that baby, you know, as an adult. My first pitch was Letterman because I just thought Letterman saying, yeah, that was me would be funny. Not that Letterman is, you know, not a normal looking guy, but just somehow that seemed like it would be a laugh. That didn't happen for one reason or another. You know, he was still in the building. He was still in NBC back then. so then somebody suggested love it and the great thing was although lovitz could not be live with us he was taping his own show out in l.A. He was willing to tape an ending and he threw in a plug for

his show so he was very eager to do it because he wanted to have a plug we didn't usually do plugs but obviously love it's you know a long time veteran of the show so it was lovitz and he there was a great moment which you may remember because you remember remember everything. He said, he comes on and says, that was me. 32 years ago. And he's clearly, you know, going to his wheelhouse of a guy telling a lie and making himself younger. And he, the way he performed that little thing, gave a little joke at the beginning. And so he had a sort of added laugh. And it was a very short ending. You don't want to be forever on a roll in like that. and it gave us our ending

and it got it in the show and this I, again, you know everything but I'll tell you this. Again, it was Victoria Jackson's last episode. She would have had nothing in the show for her last episode if not for that sketch. I had been a huge fan of her comedy

for so long, so funny, so good at her, you know, the very specific thing that she did. and to me getting something that was, I think, kind of perfect for her onto the show, getting a lot of laughs for her, playing that ditsy pregnant woman, made me really happy. Like, that was a great thing for me. And she was the one who came up and told me. That's fantastic. Yeah, she wanted to leave the show.

She had been there since, I believe, 86. And then that pretty much solidifies that you're going to be coming back. And early that season is... I mean, not necessarily. I didn't know for a while. you know, Kenny Among, you know, they call me the offer. Oh, he's a great. He's a great guy. Yeah, yeah. But he's he also, he's the, he's the money guy, you know, he's the, he's the guy that says, nope, take it or leave it. And what are you going to do? Leave it. I was weirdly, I was working on a, I had written a, for Universal, I'd written a serious drama with great help from Kevin Jar about a black cowboy in the Old West, which weirdly has become an obsession to me of the history of blacks, in the West and of slavery and things like that.

Not an obvious move for a comedy writer, but I just need a little bit of time to finish the script. So I said, yeah, can I start a little bit late next fall? He's like, nope, take it or leave it. I'm glad you took it because you wrote one of my favorite sketches. I was talking about this with Robert Smigel. You and Rob Schneider worked on, for Christopher Walk and Ed Glosser, Trivial Psychic. Can you talk about that sketch working on that with Rob Schneider?

I have to give most of the credit to Rob. I worked on it with him. I probably had some jokes in it, but it was all Rob's idea. And it was one of those sort of odd ideas that, you know, because again, Christopher Walker had been in the dead zone, right? So it was him playing himself from a movie. And that was why it was great for the host.

And then him playing himself, and you're going to have an ice cream headache. I do a terrible because we're walking. There's no one who does a worse one than me. But like him playing himself, him, as you know, from watching the show over decades, always been thrilled to be with people doing impressions of him, you know, playing with his identity and with his acting speaking style so happily.

It was great. It was thrilling. But I really have to give the credit to Rob and maybe whoever else. Maybe Lou Morton was on it too. I it was not in any way my baby but glad glad to have my initials on it yeah i believe david spade another great writer spade sandler uh schneider were such good writers they were such you'd see those initials on a sketch and just know this sketch is going to crush i don't stand a chance against these guys i mean fantastic writers not always writing for themselves either no that's very very

true. I did want to ask you about one sketch in particular, which was Luke Perry and the Magic Fish. It was kind of like a town hall and everybody with coins, you would get wishes. You wrote it with Jack Handy, correct? I think it was Jack Handy's idea. Do you recall that? Oh, my God, you have great recall or a great internet connection. I don't think I had much to do with that. I was in the room with Jack. He pulled me in, I guess. Maybe I had some jokes in it, but it was perfect sketch, perfect sketch. I agree with you. I mean, Jack is one of the legendary sketch writers ever.

I mean, you know, Toonsis and Unfrozen Caveman and so many others. But I can't. You know, sometimes you're just like, I was along for the ride. Yeah. I was in the room where it happened and got half a joke in and my initials on it. So Mark Malikoff thinks I wrote half of it. I did want to ask, was it hard to get Jim Downey in to kind of punch things up? Because I know that you wrote that sketch for Tim Robbins.

He was kind of, he was a preacher. It was like a TV show where he's talking about the Lord. And it was, I know that Downey, it was his idea for the, for Tim Robbins to punch out Rob Schneider. I believe that was Downey's idea. Did you work with him a lot? Can you talk about that sketch? Well, you always wanted to get Jim in on things, right? Because he was so good.

And, you know, you, you know, you, you, you, you, could not go wrong with getting Jim to help out on your sketch. And the punch was funny. I think he punched him twice, which is a funny piece of comedy timing. And I mean, I'll tell you, you know, Tim Robbins, obviously, he's a great actor, but I will tell you, I did give him a note. And it's interesting to me how a performance issue can affect a sketch. He played the guy he played the guy sort of stern at maybe was it

dress or at the rehearsal maybe it's just a rehearsal on Thursday and I knew that there's a look of these TV preachers which is they smile and they're talking about

people going to hell or they're talking about whatever their awful sort of right-wing theories about whatever they're not my people. But they say it with a smile that I've read the good word smile. And I said, and I don't know if I showed him tape of like Jimmy Swaggart or of somebody, but I said,

I think you need to play this with a big smile. I think it'll play funnier and the punch will play funnier. If you've got that kind of, I've read the good word smile. And he totally got it. And he played it with a smile. And I think that kind of saved it. I think it made it work. I don't know if you remember the sketch, but do you remember the sort of big sort of Jimmy Swagger? They all do it. It's not just Jimmy's right. That big like, you know, I love the sinner and, you know, that big head shaking smile about the horrible opinions they have. Yeah, he definitely played it up with Joy and the sketch did really well.

It was fun to him and Rob Schneider. I was going to ask, during this time when Kevin Eelon was doing an update, you would go in to write jokes on was it Saturday morning they would have everybody kind of congregate was Herb Sargent there at the time would he come in early on Saturday and who would you be with would you be with Kevin Nealyn? Okay so here was how it worked for a long time and again and I said this on the other podcast on typical discussing display and I said this to you on the phone and I said it in the book of guys writing about Norm McDonald. I have huge respect and affection for Kevin

and huge respect and affection for Herb Sergeant. Okay. Herb is, who was, he's no longer with us, a legendary comedy writer. Steve Allen, first writer for Johnny Carson. I mean, ladies man, Gloria Steinem. He dated Lauren Bucall. He's a Hollywood legend, yeah, for sure. Hollywood legend and an SNL legend. And was at the helm of, I don't know for how long would I.

sort of thing forever the helm of Weekend Update. You know, I could never compare it to his contribution to Weekend Update and really to the show. Like, he was a mainstay. I remember that, seeing that name when I was, you know, in high school, I think. And much of the writing for update would be done by just him and Kevin. And then at the very end of the week, there was the Update Breakfast. And the Update Breakfast was earlier. or on Saturday night, then you, I'm sorry, on Saturday morning, Saturday maybe 10 o'clock,

then you'd normally come in because you've been up working on stuff Friday night, and your whole schedule was go to bed at five, you know, wake up at, you know, one. So, but if you, especially if you didn't have a sketch in, or if you wanted to just contribute extra hard and get extra credit, or if you just wanted to help out Kevin or whatever, you'd show up for that update breakfast, and you'd grab all these AP and, I guess, UPI, black and white photos would come over like the facts or some sort of teleprinter machine, and you'd go through these black and white photos, and you'd write jokes based on the photos, and also based on the news, and you'd look through the times and the post of the daily news for odd stories, whatever,

half based on stories, half based on the news. And you had these quite good breakfasts, these lovely sort of home-cooked egg breakfast, which would be cooked right there in front of you, So you had the lovely smell of like eggs and toast and bacon right there in the big room where we did all the rewrites and we had the table reads. And it was sort of a comforting way of saying, even though my sketches did not get in the show, I'm still in it. I could be getting stuff in. So it was a nice place to be. And then when Kevin was replaced by Norm, I felt like that should, that process should not. begin on Saturday morning.

And by that process, I mean the process of bringing in other writers. And that all week long, everyone on the staff should be writing update jokes. Because that never happened because back in the day, Dennis Miller and Herb would start on Saturday morning. Kevin Neillen would start on Saturday morning with her for the most part. So you were the first one and now they do this. We're going to write. But I do want to let me back up and take away much of the, much of the credit for being the first one of anything.

There were people, Steve Corrin was, I believe, originally hired as just an update writer. He'd been writing so many freelance update jokes. Bruce Handy had been an on-staff, although maybe not in the office, freelance joke writer. And there were other people who would write jokes during the week. So to say that there was a hard line of nothing happened until Saturday morning would not be accurate. They had the faxers, which we can talk about it a little bit. They had the faxers. She would send things in, but yeah.

What I did when I took over with Norm was, first of all, make a list of the stories starting Sunday night, read everything, and make a great big list in Xerox and then hand it to every writer. Because everybody wants to get a joke on update. Jokes on update can utterly kill. You can have applause for these jokes. And it feels great to get that joke, and people remember a great update joke for years. So I would just pass them around. It's like there isn't a lack of free time there. Even though you're working super hard on sketches, you're also sitting around.

And why not sit around with a great big, I think legal-sized piece of paper with 35 or 40 topics on it, starting Monday or Tuesday? And just be thinking of stuff and giving it in. And then the big thing was that I certainly talked about on typical discussing display was going, with Norm to Carolines and then to the comic strip and having him test out these jokes before he did them on update. So before you even get to dress, you've tested them in front of a crowd. And that, I think that was my innovation. Who knows? Maybe Dennis did that too. I have no idea.

Not to my knowledge. I don't think he did. I don't think so. But that's very exciting that you got to spend time with Norm and he would do with all the jokes. there was there were a million great things about it first of all obviously spending time with norm just sort of talking about life and about comedy in the in the cabs because we just take calves because we just take calves so we probably just took cabs because you want to just sort of go from place to place and at mike sweeney who's been you know producer headwriter at conan and

still working with him he he ran the friday night show at caroline so he was always happy to get us up there and of course the audience is happy to see norm because even that early like Norm was legendary among comedy fans. So it was a great way to test stuff out and just like get to dress. And these jokes had already been seen by two live audiences. That's incredible. I know that this was completely different because Herb was very territorial about not wanting anybody else to contribute.

And this was basically the exact opposite. Herb was with Norm in the very beginning or the first couple shows. Is that correct? Yeah. I don't want to say more than that there was some conflict between me and Herb. Okay. And I loved Herb. And I did not look for that conflict. But I did feel that he was not the ideal person to be supervising update with someone like Norman. He wanted it to be completely traditional. And Norm wanted to do the clash and have it be kind of punk. I can't. Again, I can't say that I necessarily believe that's the case.

it was really me thinking, I think I've got this. I know this guy's comedy. I love working with this guy. We're clicking and it's not working with Herb. And it was, you know, it was not a pleasant few weeks. And I was backed up by Jim and by Lorne.

But I, my God, you do not want to have creative differences with people you love and admire. You had reverence for him clearly, but he was not a thing. it with Norm. It was extremely clear. Leading up to Norm doing update, it even made the trades.

There was talk that he was going to do it with Laura Kightliner, and it made what, maybe Variety or Holly reported that it was going to happen with the two of them. They were going to do it as the first duo in a long time. Do you recall that happening? And at what point in the process did they decide we're just going to have Norm? I never heard the Laura Kightlinger thing. But I, but this way, I don't remember it. your recall of my time at SNL is so much better than mine. And again, two anchors has worked so well.

Obviously, Colin and Michael is unbelievably good. Yeah, they're a powerhouse. And, you know, Dan and Jane was unbelievably good. So I don't know what to say, except I don't remember that being an option. So I know for a weekend update with Norm MacDonald, you brought in Drake Sayther. Was he brought in for show number one or was he brought in a little bit later? It was definitely later. And, you know, we had all of these great freelancers of whom he was won. And it was actually down to between him and a super funny guy whose name you might know if you worked on tonight show stuff, Tony Desana. Oh, yeah, Tony's great.

I know, I know. He wrote for Kevin Eland for a little for update the year before. Yes, he did. Tony was a joke machine, and it was down to those two, and honestly, it could have gone either way. They were both fantastic. They both got Norm. Drake was someone who had known Norm as a stand-up. They were friends.

So we went with Drake. But, you know, it's one of those horrible things. When you're ever hiring people and you get down to two, and the person that you say no to, you know, you try to be super nice about it. And all they hear is you didn't get the job. and what you mean is like it was a coin toss. It worked out well for Tony. I mean, Letterman, Johnny Carson, S&L. I do want to point out, do I have this right,

that you were writing personal checks to some of those freelancers out of your pay? Well, yes. I mean, I think I might have said this on that other podcast. So the idea was it wasn't really, it wasn't really according to guild rules allowed. They did it for years, though.

Up until recently, I mean, it was going on up until like, I don't know, five, eight years ago they were doing, still doing it. Yeah. And it's like, and like if you look at the classic, you know, everybody since the history of comedians has been paying cash for jokes. I mean, Joan Rivers, I think it used to be like 25 bucks a joke. Like, and like, that's what you do. And you and some people, hey, I made some cash. And my joke was on the tonight show. So like, nobody has ever complained. But it is not strict. allowed by the guild and certainly would have been very tough for S&L as a signatory to write these little checks. And so I think Kevin probably wrote his own checks. And I made a deal with Norm. Look, let's pay $150 a joke and we'll split it. As it happened, I was never actually paid back.

So I was writing these checks $150. But let me just say, this was never for me about like, coming out financially well. This was about making update good. So frankly, I would have paid even more money on my own bank account to get great jokes on update. I mean, one great joke, it's sort of the tent pole of the whole update and a great update. You know, Jim Downey always talked about the idea that people will stick around until update, people who like maybe would like to go to bed. And they'll stick around until update. And if update is good, even though update has zero relationship to any of the sketches, they will stick around for the rest of the episode.

So you really want a strong update. So yeah, and I wanted it to be great for Norm. So I did not mind writing those checks. And, you know, it was my, I think of it as like, is a labor of love and a gift of love for Norm and whatever. That December of weekend update, that December of 94, when Norm's first year, you were one of the writers of Sandler. Hanukkah song. You, Lou Morden and Sandler, I have to ask, what are the residuals like on that? I mean, they still play it all the time every year on the radio. They're pretty good. They're pretty good. But again, I'm not retiring. It's not like, you know, about a boy where, you know, Hugh Grant never has to work again because of one Diddy, one Christmas Diddy. But,

I mean, I've never totaled it up. I don't think I've made 50,000 off that, so it's south of that. But let me just say, and I've said it before, once again, it sounds small-sy, but it's not about the money. It's about seeing like a giant arena full of people, you know, Jews, goys, you name it, all singing like the Stooges verse together. And that gives you goosebumps and that stays with you forever. And that is, I mean, honestly, that's priceless. Stranger singing those words and also the feeling like, I mean, okay, Hanukkah's never had a great song. Right?

Let's just be honest. Draddle, draddle, draddle. At that. Okay. And like that's the tune from like when you lose a video game. Da-da-da-da-da-da-do-da-do. Like, and then Hanukkah song, and God, you got to give credit to San, it made Hanukkah cool and funny, right?

Iconic. It's unbelievable what that thing did. What was it like being in the room with Al Franken when you were writing the Chris Farley show for Paul McCartney? Was Chris also Farley in the room with you? And I know Franken works really, really kind of quick. That's his process. What was that like being in the room with him for that? Well, that was great.

It was always a great experience writing with Al because he banged it out. You know, he had wife and kids at home. So he tried to be a little bit more on a normal schedule. He wasn't quite like those single, slightly younger writers who had nothing tying them to the real world of 9 to 5. And he's just like an organized guy, you know. And so he had this big, you know, CRT desktop, IBM PC type computer. You go into his room. And he's very humble throwing jokes back and forth.

But just getting it done. He's typing, you're sitting there across from him, and you just get it done. He said a great thing. He was really, really welcoming when I got there. And he was self-deprecating. And he said, I'll do a terrible Al Frank, good impression. Yeah, I'm kind of like Phil Esposito. The guy who stands near the net and just knocks the puck in.

You know, I get the easy ones. And, of course, he's being self-deprecating. He's written legendary great sketches and been, you know, done everything on the show. Was Al the first sketchwriter at SNL that used a computer? Everyone else was using yellow legal pads and pencils and then hand in that in. Was Al the first? No. No.

He was not the first. You know, people were using MacBooks. By then, I was using, I was still back in the Windows world. I had some kind of crappy knockoff. And I think Jim was still writing on yellow legal pads. But the yellow legal pads were still a thing. We still had typists. There were still people turning things in on, you know, pencil,

on yellow legal paper, you know, staple together. But, yeah, no, Al was, Al typed at a computer. In your opinion, do you think the best sketches were selected after the readthrough based on laughs? Yes. I mean, if it destroyed at the readthrough, it would be pretty hard for it not to make it in, and there would have to be some specific, almost like a technicality,

like it bumps with another sketch, or there's a personal reason the host doesn't want to do it, or we just can't, this needs a certain physical position in 8H, and we don't have that spot because we have another sketch there. But if it destroys it the read, I mean, that's what we're looking, for it. Now, it could not destroy, but the host loves it and the host wants to do it. And then it could get in and maybe, maybe it'll do better address and error. But sometimes like if it eats it at dress, that kind of gives people pause about saying, let's do it at air.

On Mondays, when you would meet the host, would you do real pitches or do you do fake pitches? And who were some of the other people that would do some of your favorite fake pitches? is. You know, that was always an interesting question because the case for a fake pitch is that you don't want to blow the surprise of your sketch. And so if you're going to say the premise, well, sometimes you get to the premise of the sketch on page three or four and you don't want people to know. On the other hand, lots of things happen between Monday and then Wednesday, you know, midday when you start your table reads. So people are likely to forget. So I don't know. I think I mostly would pitch the actual sketch I was planning.

But also, it's Monday night. You might not know what you're going to write, right? Because it's the crucible. I always call it the crucible of fear and desperation of like it's Tuesday at 5 p.m. You don't have anything yet. And somehow that makes you come up with something. And I think just constantly doing fake pitches, it sort of undermines the host. All they hear is like, oh, we're not taking this seriously.

We're not going to tell you where we're coming up with. Kevin Neal would have a funny thing where he would, when they get to him, they're going around this very crowded Lauren's office where everyone's sitting on the floor and crowded onto couches and things. And Kevin would go, let's see, what would be funny? And, you know, Kevin is such a perfect actor of things like that of like showing what's inside his head. And it was always, it was great. The idea that like, here's how much I care about this host.

I have not thought about this yet. No, just make everyone laugh. I love that. Yeah. I mean, that's what you want. You want people to laugh. Sure. You want the host to laugh and to feel like I've joined a group and they're sort of hazing me, but I'm also the guest of honor.

And so we're all in this together. like we're all in, you know, we're in the cool, the cool bunkroom at camp and everyone likes me and we're goofing around. I was talking to Fred Wolf. Fred Wolf mentioned that you wrote some sort of diagram on some of the sketches that he would write for Chris Farley. Can you elaborate? No, can you elaborate? Yes. I believe Fred Wolf said that you wrote something that was like, it was like an arrow for Chris Farley's sketches where it was like, it gets wet,

screams, yells, something like that. It was a long time ago. Jumps into the polar beer. Yeah. That might have been, I mean, no one wrote for Farley and Norm like,

like Fred did. Fred just had a, he just had a knack for writing for those guys like black, you know, not black, dark, funny, extreme stuff. I mean, you just,

no one could do it like him. I mean, the guys, the guys are brilliant comedy writer. I know that you would write with Sandler a lot. You wrote Gap Girls, you did Canteen Boy. Okay, but Gap Girls is mostly him in spade. Again, I was in on it, but I would love to take more credit for that.

That was super funny. Was Canteen Boy, you and Sandler then? Canteen Boy was 100% Sandler, but, you know, the legendary canteen boy, was there just one canteen boy or were there more? No, there were a couple, but the one that people still talk about is Alex. Baldwin of December of 94. Yeah, okay, so Alec Baldwin as a child molesting, you know, scout leader. And that was written to some extent during the Monday night or was come up with

and then maybe partially written during the Monday night dinner. Like, you know, we took the host out and I went along. I think Kevin Neeland was there. You know, sometimes if Lauren wouldn't go with. the host, if it was someone that it was so comfortable with the show and with the cast of the writers that they didn't need

sort of Lauren's presence and handholding. Oh wow, I thought he always went. I didn't know that. He didn't always go, and I believe he wasn't there then. It was me and Downey. Okay, maybe I'm just remembering all this. I remember it was me, Downey, Spade, Kevin,

Alec Baldwin, and maybe some other people. And Spade had, it was Spade's idea. What if, what if Alec Baldwin, you know, molest canteen boy? And obviously, may I also say child molestation isn't funny. But this sketch was to my mind very funny. And we, I think we kicked it around there a little bit at dinner. I think it was this place Patsies maybe.

And Alec Baldwin was a real sort of foodie and loved certain things and told us what to order. And then we sat there kicking it around. And I didn't write a ton of it. You know, I give most of the credit to Spade and Jim. I think I wrote Canteen Boy You Rascal, which was like the end of it. The sketch people still talk about it. it is one of those things. At this time period, a lot of dark material was getting in and comedy.

I mean, just the year before or so, they did that whole Chelsea Clinton cold open with Madonna, where you could never do that now and mock a teenager of a president, of a child, and that got in on a cold open. Yeah, I think didn't we apologize for that? I think that there was an apology. I mean, Clinton wrote Phil Hartman or Lorne Michaels a letter,

and it was, yeah, that was Harvey, Kytel, I believe it was 93. They did a cold open and Julius Swaney playing Chelsea and you just couldn't do that. So I'm just, my point is, is back then, a lot of dark mean stuff was getting in at the time around those years. Yeah, I think that was probably

a mistake. But yeah, I mean, Julia was funny. She got a big laugh, but it did very well in terms of the studio audience, but yet to look at it. Now, I was going to ask you, what is your favorite time of working with Phil Hartman, either Saturday Night Live or the

Sims? sense. Well, I mean, his characters, you know, I mean, Troy McClure, Lionel Hutz, Troy McClure especially, there's just, you know, there's only, there'll only ever be one Phil Hartman, you know, and some people you would replace on The Simpsons, some people you wouldn't. And Troy McClure, just something about that, the writing of that character and him acting, it was just utterly perfect. And I think a fish a fish called Wanda was

the first table read I was at perhaps when I got there and just seeing how great he was because it was a Troy heavy episode. And I mean there were just too many at the SNL for me to pick one out. I have to think hard about it.

But he was such a good cold read. He was so good at playing this. I mean, I mean, my first sketch where he's playing the, we talked about it last, last time we talked. Yeah. The, the, the, the,

the, the, the, the, the, the, feel abuse lapathon, he was playing that kind of, and again, he's just, it's a supporting role. He's gone very quickly, but he was just perfect with a slightly anal dad, just like, can we actually know, keep the cigarettes away? Oh, good. You mentioned, I didn't know this,

that Farley called him gluey. I knew that people, yeah. He was the glue that held the show together. Yeah. Carly would call him, I'm gluey. I didn't know that that's what Barley would call him. Maybe. I mean, I think like, I mean, Keenan, my God, Keenan right now is he's so good. He's so electric. You see his face and you laugh. He's always perfect. And I feel like he's kind of the fill. Like, may he stay there forever? I mean, my God. It might happen.

At what point did you find out that for suddenly Susan, they were. We're going to have Eric Idol play a character named Ian Maxstone Graham. Well, that was really interesting. So the two people who are running the show or who were, I don't know, the ones who asked me, it was Mark Driscoll and Maria Semple. And they're both good friends of mine. I've known them for, you know, decades. And I think it was, let's say it was Maria who called me up, I think I was at the Simpsons and said, you know, we just need you to sign. something saying you won't sue us if we use your name for the Eric Idol character on

suddenly Susan. And my response was, I am going to sue you if you don't use my name for this character. I mean, it's Python. I mean, okay, a Python, so there's like the Mount Rushmore of comedy for anyone of my era or many eras who want to be a comedy writer, a Python playing a character with your name. And then, you know, at the, at the ask, we went to the Aspen Comedy Festival with, uh, with the Simpsons and did some, uh, some live, some stage readings. And Eric Idol was there for some other reason. And I'm able to walk up to him and say, hi, I'm Ian Mcstone Graham. And I think, I think maybe he said, no, I'm Ian Mcstone Graham. So, and then of course, I worked with him on the show on, on, uh, on the Simpsons. We, I, uh, actually directed him for, uh, I think,

didn't come up with the Michael Apted character, the documentarian, but I did direct him a few times for that. And again, what are you going to, you work, you work with your, you get to work with your idols, you know, like, no pun intended, you get to work with these, these legends. Absolutely, absolutely. Ian, thank you for doing this. I really appreciate it. E.M. Max, don't Graham. The next season that we do of Inside Lightning, would you come back as a guest, please, so many more questions or would you consider coming back? I will happily come back to hear the questions and to have you remind me of many things about my life that I completely forgotten. Thank you, sir. Thanks for listening. Please subscribe so you never miss an episode on Apple podcast.

Please rate it and leave a review. Be sure to go to late-nighter.com for all your late-night TV news. and you can find my podcast at latenighter.com forward slash podcasts. Have a wonderful week, and I'll see you next Tuesday.