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It took this 'New Yorker' cartoonist 25 years to achieve his childhood dream

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. If you're a fan of New Yorker cartoons, you've probably seen and enjoyed the work of my guest, David Sipress. Since 1998, he's been a staff cartoonist at the magazine, where he's published about 700 cartoons. In 2012, during the presidential campaign, he became the magazine's first daily cartoonist on The New Yorker website. He did daily cartoons again in 2014 and twice in 2016, during the presidential primary and the campaign. His new memoir - "What's So Funny?" - is about his life and about cartooning. The book is illustrated with his cartoons.

David Sipress, welcome to FRESH AIR. I love your cartoons. Thank you for being here. Let's start with your most published and tweeted cartoon. Would you describe it?

DAVID SIPRESS: Yeah. It's two people walking down the street, a woman and a man. And the woman is turning to the - well, she's sort of looking up at the sky and saying, my desire to be well-informed is currently at odds with my desire to remain sane.

GROSS: That has been true for so many years right now (laughter). When did you write it?

SIPRESS: I wrote that sometime during the '90s. It's not a New Yorker cartoon. I never can remember where it first started, but I think it was during the whole Bosnia problem. And it was so upsetting getting up every day and reading the paper, something we're familiar with right now. And every time the world goes, you know, down the toilet, that cartoon begins to show up all over the internet. And I think what's interesting about that cartoon is it's not actually funny, you know? It's not a joke. It's something I've learned to do about these difficult things that happen in the world, how to make a cartoon about them. And I try not to hit them over the head or go straight for them. I try to think about what I'm feeling about what's going on and make a cartoon like that one, which is - it was exactly how I feel right now about everything going on. And after 50 years of doing this, I've discovered that my feelings match the feelings of my audience a lot of the time. And it's that moment of recognition that creates the humor rather than an out-and-out joke.

GROSS: As we record this, there's a 40-mile mile convoy of Russian tanks heading toward Kyiv. So on days like this, do you think about cartooning, or do you feel like this is not the time for cartoons or at least topical cartoons? It's hard to find anything funny about what's going on now.

SIPRESS: It's not the kind of thing that sends me to my studio to think up cartoons. It's just so dangerous to attempt to make a joke out of a terrible situation like this. Maybe in a week, maybe in two weeks, maybe when things calm down, I'll be able to go back to this strategy I have of trying to make a cartoon about what our response is to the events, not a joke about the events themselves. But right now I really feel like I need to back off of that and think about things like a cartoon about what I had for dinner or how I don't have enough money in the bank.

GROSS: You've spent a lot of time doing daily cartoons for The New Yorker's website. You did it in 2012 during the presidential election. You did it again in 2014 and twice in 2016. You did it for the presidential primaries and the presidential election. How did you see Trump and the primaries in the election differently having to do daily cartoons than you might have if you weren't doing that?

SIPRESS: Well, the first thing is that the kind of avoidance I was talking about a moment ago was not possible. I was forced every single day to open the newspaper and try to come up with something and to come up with something fast because by 8 o'clock I had to send in my idea. And it became more and more difficult during the Trump years, precisely because Trump sort of trumped cartoons and trumped jokes, at least for me. Cartoons depend a lot on exaggeration, and all the exaggeration started to come true with Trump, at least for me. So I found it harder and harder to make cartoons about him, and I turned my attention to other aspects of the news, eventually. And I also think the audience was getting pretty tired of Trump jokes. So during that latter part of my stint as daily cartoonist, I tried more and more to avoid him. Or if I did depict him, I started depicting him not as Donald Trump, but I would create sort of a medieval setting and use him in the position of a king. And, for example, there's one cartoon I did of the king saying to one of his advisers, I don't know much about science, but I know what I like.

GROSS: (Laughter) That is funny.

SIPRESS: And that was a way of saying something about Trump without depicting him or going at it directly.

GROSS: I want to get back to Ukraine for a moment. Your father emigrated from Ukraine when he was a child with his parents. He was born in 1905. Did he talk much about what he left behind in Ukraine and what it was like to, you know, be on the ship coming to America and land here?

SIPRESS: Well, a lot of the theme of my memoir is about secrecy and spending my - a life trying to get my father to tell me anything about that distant past. I don't think it's unusual for immigrants of my father's generation to have that sort of urge to forget about all that and not talk about it. My father was kind of an extreme example. I just could never get any of my questions answered, and anything I figured out about it I figured out on my own by overhearing conversations, doing snooping around the apartment into records and even just going to the library and reading about what was going on. But there was very little about my father's immigrant past that he ever talked about, except to say things about how terrible crossing with all the hoi polloi, as he put it, in steerage was.

And then finally, if I can do - and I'll say another cartoon. What I ended up with was - I expressed in a cartoon I did a few years ago of a father and a kid standing in Brooklyn, sort of looking towards Manhattan, and the father is saying, the country I came from was a stinking hellhole of unspeakable poverty, where everyone was always happy. And that was sort of the mixed message that I got through all the secrecy. But that's about as far as I got with information until just before my father died.

GROSS: I want to mention another cartoon that you've done that kind of combines your work as a cartoonist for The New Yorker and your life as a patient in therapy. Can you describe that cartoon?

SIPRESS: I think it's - I think the caption is - it's the patient lying on the couch with a therapist, and sitting in the corner is a woman with a notepad, and the therapist is saying, that's Eleanor; she'll be fact-checking your therapy session.

GROSS: And, you know, the New Yorker is famous for its fact-checking. Do you worry that the things you tell your therapist might not quite be accurate?

SIPRESS: Well, you know, that's such an interesting question because, really, where that whole thing came up was about writing this book and about memory. And in fact, one of the things that I learned in therapy was that, in a way, it doesn't really matter whether the facts check out because the stories that you tell yourself about the past have their own truth, a truth about you. And that was really helpful to me in writing my memoir because I don't have many sort of first-person sources. I only have what I remember. And if I stop myself every page to think, well, if a fact-checker looked at this, they'd know that such and such didn't happen, I would never have finished the book. So at some point, I sort of let go of the need to fact-check and just wrote my stories. And I think I can say that they have a truth that is absolutely genuine, as far as I'm concerned.

GROSS: Well, let's take a short break here, and then we'll talk some more. If you're just joining us, my guest is David Sipress. He's a New Yorker cartoonist who's written a new memoir called "What's So Funny?" We'll be right back. This is FRESH AIR.

(SOUNDBITE OF BRUNO COULAIS' "SPINK AND FORCIBLE")

GROSS: This is FRESH AIR. Let's get back to my interview with David Sipress. He's been a New Yorker cartoonist since 1998. He has a new memoir called "What's So Funny?"

You tried for years to get published in The New Yorker. What was that process like of constantly submitting cartoons and constantly getting rejected?

SIPRESS: (Laughter) Well, yeah, it took me 25 years of submitting. And people often say, well, why didn't you give up? It must have been dispiriting. How did you keep going? And I did keep going precisely because if you do what I do, which is make single-panel cartoons, there really is The New Yorker and then everything else. And so since my dream from the time I was about 6 years old was to be a New Yorker cartoonist, I wasn't about to let all that rejection get in the way. I would just tell myself every week, you're good. You're as good as the cartoons that are in there. Someday somebody's going to figure that out. And I just kept submitting. I'd take a month or two off every now and then, but I always got back to it. And I can tell you that the day I got the fax from the new cartoon editor who replaced the old cartoon editor who had been rejecting me for all those years - the day I got the fax that I'd sold my first cartoon was perhaps the happiest day of my life.

GROSS: And that new editor was Bob Mankoff.

SIPRESS: Bob, yes.

GROSS: So was there a kind of cartoon that you submitted to The New Yorker for the 25 years that you were trying to get in?

SIPRESS: No, I never - you know, a big mistake a lot of people make, I think, is that they try to do, quote, "New Yorker cartoons." I just continued to do David Sipress cartoons. I thought what I thought was funny was funny, and I just kept doing it. And I just needed them to adjust, (laughter) you know? I need them to expand their idea of what a funny cartoon is, what a good cartoon is. I sound very relaxed and adult about it now. The honest truth is, a lot of that time I felt pretty - I have a cartoon in the book where these two sort of guys are sitting on the street. They're obviously homeless and destitute, and one's saying to the other, OK, maybe failure is an option.

GROSS: Yeah.

SIPRESS: And I - that does - there was a lot of that thinking that went on that I had to push aside.

GROSS: How did you keep submitting? Was it through the mail or did you knock on doors? How did that work?

SIPRESS: I lived in Boston for a lot of that time, and that was by the mail. But I started coming in in person on the look day, which is Tuesday, once I moved to New York in '83. But that had its own sort of frisson of humiliation because the people who were already in the magazine got to go into the inner sanctum and meet with the editor, and those of us who weren't had to just hand our batch to the receptionist. And then you'd come back on Friday morning, and you'd get your batch and you'd stand by the elevator and say a little prayer, and you open it up and there was your rejection slip. So (laughter) - but I did do it in person from about '83 to '97, when I first got - when I sold my first one.

GROSS: Your father kept telling you to give up on the idea of being a professional cartoonist and go back to pursuing a career as a historian. You studied Russian history at Harvard before you dropped out to pursue a career as a cartoonist. Did that get to you to? Did that ever get to you, his very discouraging words about your dream?

SIPRESS: I think I never really got over the desire to have him approve my choices. It was really hard at the start. There is a chapter in my book about my response to his finding out that I had dropped out of school and the anger that he expressed over the phone and how that nearly destroyed me, really. And I hadn't even realized to that moment how much his approval and support had meant to me, and to not have it anymore was pretty upsetting.

And even, you know, to the end - I tell in the book that I - when I did finally sell a cartoon to The New Yorker and my - even my father can - would see that a cartoon in The New Yorker was some kind of success, maybe not as big a success as being, you know, the ambassador to the United Nations or a hotshot lawyer, but he recognized that as some kind of success. And when I sold that first cartoon, the first person I called after my wife was my father. And then - what I didn't know was that when you sell a cartoon to The New Yorker, it doesn't mean it's going to appear that week or the next week. In fact, I sold that cartoon in October, and it didn't appear until July. And sadly, in the interim, my father died and never got to see it. And every week until he died, he would say - call me and say, David, I got my New Yorker. You're not in there.

GROSS: (Laughter).

SIPRESS: And said, are you - then he started saying, are you sure you sold that cartoon, you weren't just dreaming that? (Laughter) So the great disappointment was he never got to see it.

GROSS: When he looked into the future, your father always saw a negative outcome. So what - always, like, a worst-case scenario that he predicted. Are there examples that you remember?

SIPRESS: Yeah. I mean, he - what he - almost about everything - I finally figured out that what he was doing was he was sort of giving himself a preemptive shot of disappointment and pain so that when the thing - bad thing happened, it - he'd at least be prepared. And he did that about everything. You know, if he was going to the doctor, you - all he'd - you'd hear him say things like, this pain in my back has got to be back cancer. He just always expected the worst. And there are a million examples, but - including about me, you know, that these choices I was making were going to wind up ruining my life. So there was always this what I called negative chicken counting from that expression don't count your chickens. You usually say that to people about - you know, don't count your chickens about good things that are going to happen. Well, my father was always counting his chickens about bad things that were going to happen.

GROSS: And he probably wasn't aware of that. It strikes me - your father doesn't sound like a very introspective man. He didn't speak the language of psychology. You have been in therapy for many years and really appreciate the help that it's given you in understanding your life and the stories that you tell yourself about your life and about your family. And I'm wondering if that was a source of frustration for you, to see things that he was doing, to see his, like, negative chicken counting knowing that he didn't see that and that he wouldn't see that.

SIPRESS: I understood that almost from the time I was a small boy. I understand that - what I say at one point is my father always looked out, never in. Someone was saying to me recently that people of that generation who had real problems and real difficulties when they were young - I mean, real-world ones - didn't really have time to develop that sort of inner life that those of us can indulge ourselves in these days.

But it - all through my life, I didn't have that perspective. I just kept being frustrated that I couldn't have a conversation with him about how he was feeling about something. I couldn't have a conversation with him about the ways I felt he was getting in his own way because he just never - as you said, he just never looked at the world that way. And, you know, I've been in therapy for much of my life, and my father never, as I say in the book, spent a millisecond, quote, "working on his issues."

GROSS: (Laughter) Yeah. Your father's attitude was no one ever said you were supposed to be happy. Like, when you told him you were dropping out of Harvard where were studying Russian history so that you could pursue a career as a cartoonist, he said to you, what, because you're unhappy? You're unhappy? That's it? That's it? And you quote him as saying, listen, mister, who's happy? Nobody, that's who. You think life is a bed of roses? After all we've done for you, this is how you repay us?

(LAUGHTER)

GROSS: And that sounds so familiar. I think so many parents and maybe especially Jewish parents of that generation or immigrant parents of that generation - I don't know. But I think you have a lot of company in having parents who would say that. Where do you think that comes from?

SIPRESS: I think it comes from the difficult story that my father was so reticent to tell me about of where he came from and how he got to be where he is. And the whole time, being a Jew and being an immigrant, there just is a natural pessimism that comes with that. And happiness - who has time for happiness? When my father said that to me, I even said, at that moment, that telling him that my desire was to be happy - even that sounded pathetically insufficient to me because I had been so ingrained with his point of view.

And I'm not 100% sure where that comes from, but I think it has something to do with the difficulty of becoming the totally assimilated American business success that he was and how hard that was and how much work there was involved in that and also wanting me to do something that he could be proud of. And as far as he was concerned, those are the kinds of choices that involve hard work and suffering. Cartooning to him just looked like I was just fooling around.

GROSS: He probably also thought he was protecting you from inevitable failure.

SIPRESS: His attitude about happiness really never entirely left my subconscious. And it's funny because I actually still might have a little bit of residual guilt about this career choice that I made - that it's too much fun, that I'm having too good a time, that I should be suffering more. I - what I tell is that I don't work at home. I always have a separate space that I go to to do my work - which a lot of cartoonists do, and I think that explains a lot of the desert island cartoons - because I need a separate place that's completely quiet and my own.

And it's also a way of fooling myself into thinking I have a regular job, you know, that I'm going to the office every day instead of just sitting - getting out of bed and starting to work at home. And I think that has to do with the guilt I've always felt about choosing such a fun profession, that maybe it's not serious enough. So I still, to a certain extent, carry around my father's notions of happiness.

The thing that I realized towards the end of the book, ironically, was the only time I ever saw my father really happy when was just - when he was working. I - the only time I saw him not suffering was when he was in his store, dealing with his customers and being proud of everything he'd accomplished. And so in spite of the fact that he told me that real work involves suffering, I - at some point, I realized, well, he wasn't suffering at all at work, (laughter) so...

GROSS: Well, let's take another break here. If you're just joining us, my guest is David Sipress. He's been a New Yorker cartoonist since 1998. He has a new memoir called "What's So Funny?" We'll be right back after a short break. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF MISHA MENGELBERG TRIO'S "A BIT NERVOUS")

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with David Sipress. He's been a New Yorker cartoonist since 1998. He has a new memoir called "What's So Funny?" In the memoir, he writes about his life, but he also illustrates the book with a lot of cartoons relevant to the period of his life that he's writing about.

You know, I think a little bit about the trauma that your father must have suffered coming to America. The family escaped the pogroms and conscription into the czar's army, and then they were nearly turned back at Ellis Island. What did your father tell you about that? This is one of the few things I think you know about his past.

SIPRESS: He only told me that the last time I ever spoke to him. My wife and I were leaving for a trip to England and I went to visit him before we left and he died while we were away. And so it was the last conversation I had with him and he was waxing nostalgic and for a just about five minutes opened up a bit about the past and about his mother. And he told me how proud he was of his mother. He almost never mentioned her. She was like a queen to me, he said. And then he described the incident of coming to Ellis Island after that incredible journey across Europe and in a horse cart and then a train and then the passage over the ocean in steerage. And they get there and they're not going to let him in because one of my father's brothers, oh, I don't know what the correct term for it is, but he was - my father said he was a hunchback. And they weren't going to let the whole - they weren't going to let him in, and so that meant the whole family was going to have to turn back. And somehow, he didn't know how, his mother dealt with that. And next thing he knew they were all marching out of the building and on their way to Brooklyn. And that was the moment where, for the first time, I heard my father express admiration for his mother and real love for his mother.

GROSS: What impact did that story have on you?

SIPRESS: Well, for one thing, when I listened to him tell me that story, I thought, well, what were my problems when I was a kid? You know, my - I couldn't have a dog, my mother had migraine headaches, my sister teased me all the time. Look what he was dealing with. And it - when he when he told me that, I found myself beginning to forgive a little for all the other stuff and understand him a little better. But really, what happened was that the next impact on me was he started coughing and I went in and got him a glass of water and by the time I came back, he didn't want to talk about it anymore. And I swore to myself that the next time I had a chance, I was going to get - find out more. I desperately wanted to know more, but my father died and I never had that opportunity.

GROSS: So you just compared the problems you had growing up with your father's problems. But some of those problems that you had were significant. Your mother had debilitating migraines where she would, like, shut herself in the room for days and you weren't allowed to talk with her, you weren't allowed to open the door, so you felt really unloved during those moments. And then also your sister who teased you, well, it turned out she had bipolar disease, and she died by suicide after your father died. So these were actually pretty serious things you were dealing with. It wasn't it like getting, you know, sent back to the country that you just fled from, but, you know, it wasn't nothing.

SIPRESS: Believe me, I know. I do. I just meant that it was just in that moment of talking to him that I made that comparison. But yes, I dealt with a lot of difficult stuff in my life and my sister, of course, as well. So, yeah, there were problems, but the, quote-unquote, "real-world problems" that my father dealt with at that moment seemed to overpower any thoughts I had of any of my own difficulties.

GROSS: There's a story you tell in your book about bravery, about your father's bravery when his jewelry store was robbed, and I'd like you to tell us the story.

SIPRESS: My father had a jewelry store in Lexington Avenue in Manhattan for many - for decades, and he was very proud of what he called his security system. He would he would touch his actually very thick glasses and say he could see the who was coming in through the glass on the door, and if they didn't look right to him, they didn't get buzzed in. Well, one day around Christmas time in 1959, his security system failed. He let in two guys who he thought looked OK because they had nice overcoats and were carrying Bloomingdale's shopping bags; in fact, they came in to rob him. And there's a long dialogue in the book between my father and the robbers. And all this is being told to my mother, my sister and I as we sat around the dinner table that night. And my father - basically one of the robbers, put a gun in his face and said, give me everything in the show window, which was all the stuff that my father valued the most, and my father said, no. I worked my whole life for that. Go ahead, shoot me. And there was a series of moments like that, stupefying the robbers where he invited them to shoot him and said he didn't care. He - and by the end of it, one of the robbers said, well, you got to give us something. So my father gave them, like, a cheap necklace and a wedding ring and told them to be on their way.

And when he told the story at dinner, at first, I was extremely proud of him and I thought, wow, he's so brave. You know, he stood up to these guys. But gradually, this worm of discomfort started crawling around in my brain and suddenly this - I've heard the voice in my head say, what about me? You were willing to die for the necklaces and the cufflinks and the bracelets and leave me alone without a father. Didn't you think about me for a minute while that was happening? And that turned out to be my response to this story. So it started out as admiring his bravery and ending up with a kind of sorrow that he cared more about those things than he cared about me. As time went on, with the help of my wife, I gained a different kind of understanding about that event that helped me to see it differently and see my father differently.

GROSS: What was that different understanding?

SIPRESS: Well, just as I have a compulsion in my life, every time I'm in any situation, from therapy to walking down the street to eating in a restaurant, I'm always thinking of cartoons. It's just something that I've done my whole life, it's a compulsion. And so I recognize the idea of compulsion. And my wife explained to me, and she was right, that my father's compulsion was always to bargain. She said he wasn't thinking about the gun, he wasn't thinking about you, he wasn't thinking about dying. He was doing what he always does. He was on autopilot. He was - and this is the thing he always talked about - getting his price. He just would bargain instinctively in every situation. He bargained with me when I tried to drop - when I wanted to drop out of school, he offered me this, he offered me that. That was his way of dealing. And so it helped me to forgive him for that and to understand that he really was just being the only person he knew how to be in that situation.

GROSS: Did you ever talk to him about it?

SIPRESS: No, those are the kinds of conversations both of us were kind of incapable of. So no, I never did. I - fortunately, in my wife, I have an interpreter, a person who can always interpret those interactions that I had with my family and help me see them in a new and different way, if that was necessary.

GROSS: Let's take another break here, and then we'll talk some more. If you're just joining us, my guest is New Yorker cartoonist David Sipress. His new memoir is called "What's So Funny?" We'll be right back. This is FRESH AIR.

(SOUNDBITE OF VIJAY IYER'S "BLACK AND TAN FANTASY")

GROSS: This is FRESH AIR. Let's get back to my interview with David Sipress. He's been a New Yorker cartoonist since 1998. Now he has a new memoir called "What's So Funny" that's not only a memoir, it's illustrated with his cartoons.

There's Yiddish words that are sprinkled throughout your memoir, including farshtunkene, mishigas, fershtay.

SIPRESS: Mamzer (laughter).

GROSS: I'm sorry?

SIPRESS: Mamzer is one I also...

GROSS: I'm not sure I know mamzer. What is that? I should know that.

SIPRESS: Just, basically, a cheap bastard (laughter).

GROSS: Oh, (laughter) OK. I guess my parents left that one out to be on the clean side of Yiddish. What did Yiddish sound like to you? And what did it mean to you when you were a child and heard your parents speak it?

SIPRESS: Well, first of all, they didn't. You know, what's interesting is that somebody is doing an audio version of this book. And in spite of some of the things I've said in this discussion, I did not want my father to be - sound like he had an accent because his whole life was about becoming assimilated, becoming an American and leaving that behind. And he pretty successfully got rid of any accent he might have had. And Yiddish was only something that came out of him at moments of stress or high emotion. Those things would pop into his conversation. Whenever he and I had a really emotional moment, he would call me David instead of David. And I always knew that was when he was overwhelmed by strong feelings. And sometimes, when he was angry or some other strong emotion overtook him, the Yiddish would come out. My mother had no Yiddish in her background whatsoever. She actually was born here. Her parents came from Vienna. And she was the child of immigrants. And she never had any Yiddish. So you wouldn't expect any to come from her.

GROSS: But yet, you remember all these Yiddish words.

SIPRESS: Yeah, because when he used them, they really stuck out. I mean, and also, they're the words I love. Like farshtunken, I just love that word. And actually, my mother did use that once when she was describing all the dog doo, as we called it, on the street. She said - I was begging to let her have - let me have a dog. And she said, we really don't need anyone else adding to the farshtunkene obstacle course that 79th Street is already.

GROSS: My mother used to use it during the period when my father was smoking a cigar and would smell up the whole house (laughter). And my mother would say...

SIPRESS: (Laughter).

GROSS: That farshtunkene cigar.

(LAUGHTER)

SIPRESS: I can tell you one other funny thing about it. As I said, they're doing an audio book of my book, which is a little difficult because you have to turn the cartoons into words. But I got a note from the reader asking me how to pronounce certain things. And it was a list of some of those Yiddish isms farshtunken, fershtay, those. And then the very last one was my wife's mother's name, which is Wylene (laughter) - you know, how to pronounce Wylene.

GROSS: So you know, we've talked a lot about you. We've talked a lot about your father. Let's talk about me for a moment (laughter). You did a cartoon about me a few years ago. And it was such - it really was just, like, such a thrill. So would you describe the cartoon?

SIPRESS: Yeah. It's a cocktail party. And I draw you from behind, because I always think it's funnier to portray people without caricaturing their faces. So I tried to imagine what you would look like from behind, having never met you. And people tell me I did a pretty good job. And you're at a cocktail party. And you're talking to this sort of well-dressed couple. And you say to them, you may have heard me on FRESH AIR with Terry Gross, I'm Terry Gross.

And in preparation for talking to you today, I was - I knew - I felt you might ask me about this. And I was trying to think, well, what's funny about that cartoon? And my wife suggested that it says something about the way people behave at cocktail parties, or maybe the fact that you are a disembodied voice and you were trying to posit that you're an - actually a real person. But for me, it's one of those cartoons that I've done where I really can't say what's funny about it. And that's why I love those cartoons. It's just sort of a mystery. It's just something about it that's funny that I can't put my finger on. And that's why it's one of the ones I really love.

GROSS: Does it have something to do with somebody's name being part of a title of a show?

SIPRESS: Absolutely. But first of all, one thing you learn writing captions is that every single word, every punctuation mark, everything in that caption matters. You want the reader to glide smoothly through the caption to the punch line without anything distracting them. And you want to make everything in it as funny as possible. And, Terry, you have a funny name.

GROSS: I do (laughter)?

SIPRESS: It really helps. Gross is a funny name.

GROSS: Yeah, that's true.

SIPRESS: It wouldn't have worked as well with - I don't know - somebody else. But Gross is just funny in and of itself.

GROSS: So I just have to tell you something about the fact-ness (ph) of that cartoon. So I am depicted in your cartoon wearing what looks from behind like a skirted suit and wearing a skirt that, you know, comes, like, considerably below my knee. I want you to know I haven't worn a skirt or a dress in decades. And I want to know...

SIPRESS: I'm sorry.

GROSS: I want to know - where were those New Yorker fact-checkers when you put me in a skirt?

SIPRESS: Good point.

GROSS: (Laughter).

SIPRESS: Good point, Terry. Good point. Can I tell you the funniest story about the fact-checkers that there is?

GROSS: Yes, please.

SIPRESS: Years ago, I did a cartoon of - it's sort of an ancient scene with a ancient building in the background, and it's a guy with a sword leading a goat. And he - the goat is turning to another goat and saying, I'm having my entrails read - really excited.

Well, I got a note from the fact-checking department that corrected - that said the knife was incorrectly drawn. It should be a single-bladed knife - blah, blah, blah. They even sent me a picture - and that on the building there were five columns. And there were always only even-numbered columns, so they asked me to change the number of columns. So I wrote back to the fact-checking department, and I said, I understand your problem with the knife. I understand your problem with the number of columns. Why didn't you have a problem with the fact that there's a talking goat?

(LAUGHTER)

SIPRESS: So...

GROSS: What was the response?

SIPRESS: A big laugh from the assistant cartoon editor but nothing from the fact-checker.

GROSS: Let's take another break here, and then we'll talk some more. If you're just joining us, my guest is David Sipress. He's been a New Yorker cartoonist since 1998. He has a new memoir called "What's So Funny?" We'll be right back after a short break. This is FRESH AIR.

(SOUNDBITE OF MICHAEL NYMAN ET AL.'S "HOW DO I KNOW YOU KNOW?")

GROSS: This is FRESH AIR. Let's get back to my interview with New Yorker cartoonist David Sipress. He has a new memoir called "What's So Funny?" that's illustrated with many of his cartoons.

You wanted to be a New Yorker cartoonist ever since you were 6. Did your family have The New Yorker around the house? Did they subscribe?

SIPRESS: Oh, yes. It came every week, and my mother and - read it cover to cover. My father not so much 'cause he didn't have as much time. And I was just entranced from the very start by the cartoons. I didn't understand all of them, but I loved the drawing, and I felt so drawn to drawing that way. And so what I started to do is make my own little cartoons. And once my mother was done with the issue, I would cut out my cartoons, and I'd Scotch tape them in the magazine over the cartoons that were there just to make my fantasy come true for a minute that I was going to be a New Yorker cartoonist.

GROSS: Wow. You were really serious about it as a kid.

SIPRESS: I was. Once at our elementary school, a cartoonist came to give a demonstration. It was sort of, like, a career week thing. And he drew on a big pad in front of all of us kids, and he did all these wonderful things like ask kids to come up and scribble like crazy. And then he would turn the pad around and turn the scribble into something and then that something into a cartoon. To me, it was like a wonderful magic trick. And I went up to him afterwards. I think I was in fourth grade. And I shook his hand, and I said, I'm going to be a New Yorker cartoonist one day. So it was really what I always have wanted to do, and I - sometimes, I have to pinch myself that, wow, I actually wound up doing it. I feel so lucky.

GROSS: Do you remember one of the cartoons that you did and then pasted into a real issue of The New Yorker when you were young?

SIPRESS: Well, I remember the first cartoon I ever did. And I describe that in the book, which is just a silly pun, but it's a dog furiously barking at the trunk of a tree. And of course, the dog is going, bark, bark.

GROSS: Because the tree is bark and the dog is barking.

SIPRESS: Yeah, yeah.

GROSS: Yeah.

SIPRESS: Yeah.

GROSS: (Laughter) Do you have to do a cartoon today?

SIPRESS: I would have, but I'm talking to you and skipping this week 'cause my deadline is in about 45 minutes. The deadline for The New Yorker - we hand in our roughs on Tuesday at noon, and then they get looked at by the cartoon editor. And she probably gets a thousand cartoons, thousand roughs, and she whittles them down to - I don't know - 50 or 60. And then the next day, she meets with David Remnick, and David chooses which ones will go into the magazine. And then you hear on Friday about whether or not you sold one.

GROSS: Is it like getting graded every week?

SIPRESS: (Laughter) A little bit. And no matter how long I've been doing this, I wake up anxious about whether or not I'll sell one, wondering if I sold one this week. It's like getting graded, but it's also - having done this for so long now, the rejection is a kind of teacher. I mean, I've learned a lot from it. I've learned what works. I've learned what doesn't work. I've often - and now, this is true of all of us cartoonists. I often resubmit cartoons - sometimes with no change, sometimes with some small change, sometimes over and over. And eventually, a lot of them sell. So a rejection isn't the end of any particular cartoon.

GROSS: When you were young and your parents subscribed to The New Yorker and you loved the cartoons, who did you love? Who were the cartoonists?

SIPRESS: Oh, boy. Well, above all of them, it was Saul Steinberg, who wasn't actually strictly a cartoonist, but he was a magician with drawing. He did things with line that always surprised and delighted me and made me understand how much a simple line can turn into wonderful things. And so I was completely obsessed with his drawings. He refused to call himself a cartoonist, and he's a great artist. Of the cartoonists who are more strictly cartoonists, I love Steig, I love Soglow, I love Barney Tobey; I don't know if anybody knows these names. I love Kovarsky, I loved some of the cartoonists who are still around who were just starting then, like the great Sam Gross - speaking of Gross - who's probably the funniest cartoonist that's ever lived, but I love them all. I even love the sophisticated sort of Saxons and Arnos because they - to me, they depicted a New York that I dreamed one day I would be able to participate in, where everybody was sophisticated and everybody drank martinis, and everybody had really smart things to say. So I love those cartoons, as well.

GROSS: How did you decide what you wanted your illustration style to be?

SIPRESS: Well, I love artists like Charles Addams, who make these incredibly complex, beautifully drawn representations of what they're drawing about. I've always admired them, but it's not who I am. I wanted my cartoons to look like David thought up the idea, he picked up his pen, he drew it, he handed it in, that's it. I wanted that feeling of direct, spontaneous activity of the brain reflected in the drawing. And then at a certain point, being untrained as an artist and never gone to art school, I started looking at a lot of art, and there were some artists whose drawings, to me, gave me permission to draw the way I draw. One of them is Jean Dubuffet. I loved the sort of primitive feel of his line and his drawings. And another a little later on was Philip Guston, whose drawings also inspired me enormously and gave me permission to draw the way I draw. And also, a lot of it has to do with the pen that I use. I use a Crow Quill Pen; it's a pen point in a holder. And the wonderful thing about it is it's very, very hard to control. It's not like a radpidograph pen or anything like that. There's always going to be what artists call happy accidents, times where the pen slips a little or the ink blobs a little. And I - over time, I realized I love to leave those things in. I don't like to correct them because, again, it gives a feeling of directness and spontaneity.

GROSS: So, you know, you had a very troubled relationship with your father. When you went through his possessions after he died, one of the things that you found that really made you tear up in a way that you hadn't before was a sketch that he did of a dog. And I have to say, his lines are so graceful in it. And you didn't know he was doing that.

SIPRESS: Well, I knew that he could draw really well because he kept an inventory of everything that ever went in and out of his store. And at that time, he never would have thought of photography. He drew every single bracelet, every single pair of cufflinks, every single piece of silver. He drew them on index cards and then wrote what they were. And so he was very skilled with a pencil. I had never seen him draw anything but jewelry, et cetera. And when I was going through the file cabinet and I pulled out that card, I suddenly had a picture of him sort of stopping in his drawing of whatever bracelet or necklace he was drawing and looking up and seeing a dog on the street and drawing the dog. And that just - for whatever reason, I can't quite explain it, it moved me more than anything else. Maybe it just let me know that he - deep down, he was an artist like me.

GROSS: David Sipress, it's really been a pleasure to talk with you. Thank you so much.

SIPRESS: Thank you, Terry.

GROSS: David Sipress is a New Yorker cartoonist. His new memoir is called "What's So Funny?" Tomorrow on FRESH AIR, my guest will be novelist Amy Bloom. Her new memoir is about how, at her husband's insistence, she helped him legally terminate his life after he was diagnosed with Alzheimer's disease and decided he wanted to end his life while he was still himself. He didn't fit the qualifications in American states with right to die laws, but he did at a nonprofit in Zurich, Switzerland. Her book is called "In Love: A Memoir Of Love And Loss." I hope you'll join us.

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GROSS: FRESH AIR's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our interviews and reviews are produced and edited by Amy Salit, Phyllis Myers, Sam Briger, Lauren Krenzel, Heidi Saman, Therese Madden, Ann Marie Baldonado, Thea Chaloner, Seth Kelley and Joel Wolfram. Our digital media producer is Molly Seavy-Nesper. Roberta Shorrock directs the show. I'm Terry Gross.

(SOUNDBITE OF BILL EVANS TRIO'S "DOLPHIN DANCE") Transcript provided by NPR, Copyright NPR.