Sherry Lane: Caricaturist, Cartoonist

Sherry Lane is a self-made woman. Her interest in drawing faces led to a career that has spanned more than four decades. She has worked as a caricaturist and a cartoonist at private parties and events for colleges and major corporations. Lane has also established her own entertainment company, which currently boasts a roster of performers.

Terry Stoller spoke with Sherry Lane in October 2013 about her entry into the world of caricatures, her influences and the development of her own technique, her formal face reading studies, her caricature of Lehman Brothers executives, her drawings of political figures, her impetus to become an entrepreneur—and the credo for all her endeavors.

Terry Stoller: How did you get into doing caricature work?

Sherry Lane: Well, I couldn’t type. I had no office skills, but I always drew. I started drawing when I was in elementary school. I drew faces, mostly pretty ladies. The kids in school would ask, “Make one for me.” I would do the drawing, tear the paper off of my notebook and give it away. I was doing that in elementary school, and I’m still doing the same thing today.

Did your family encourage you to become an artist?

No. My mother had artistic talent, and my dad had musical talents. And my grandfather was an inventor, so there were genes there. But my mom said, No, no, no. You don’t want to be a starving artist. Be a teacher. I never got encouragement. When I did finally go off to the University of Illinois, I didn’t know what to do. So I did what my mother told me to do, and I signed up for education. I was really unhappy with that. Then I found the art department building on campus, by accident. I felt so happy in that art building, with the paintings on the walls and the drawings and the smell of the oil paint and the
graffiti on the lockers. I loved the whole environment. I said, OK, I have to change majors. So second semester, I switched to fine art.

But why caricature? Why did you turn to that?

Because I always had an interest in faces.

But that could have led to your doing portraiture.

Well, I had to make a living, and it’s very difficult to make a living as a fine artist. You’ve got to find a commercial niche. When I was in my late teens and early 20s, I was modeling at trade shows. I lived in Chicago, and Chicago was the convention capital of the country. McCormick Place is a huge convention center. I would get work at the trade shows as a spokesperson or a model—handing out flyers or collecting business cards. I did store modeling at Marshall Field’s, Saks, and the other major department stores. I modeled in fashion shows. I started out thinking that I was going to be a model. There was a market for that in Chicago—I did photo shoots for Sears catalog—and I moved progressively in that direction. But I was in McCormick Place one time at a trade show, and I saw an artist doing caricatures in a company booth, and I thought, I could do that. My agent sent me on interviews for modeling work. During the interview—these were with major corporations, and I was cute, in my 20s—I’d mention that I drew caricatures. I made a little flyer to show them samples, and they started hiring me to draw caricatures. That opened up a whole new world.

What did you draw on from the university art department to go into this field?

Nothing. I was just an art major, taking art courses, studio courses, art history, and whatever else was required. I didn’t know then what I was going to do.

Over the years, whom have you admired and drawn from?

I’ve looked at the historical background from Da Vinci to Daumier to the present, but the person I admired most and who had the most influence on me was Al Hirschfeld. He was the one out there. There’s another man I admired, Sam Norkin, who’s lesser known. He was the caricaturist for the New York Daily News for twenty-six years. He did parties, too, and we’d work together. At one time he did a lecture program. (I did that, too, years ago.) On the job, he was a strong influence. I loved to watch him draw. He had a style similar to Hirschfeld’s, but more angular, more sharp edges. Hirschfeld’s line was round, and Sam Norkin’s line had sharp edges. They were both masters of their craft! And another person I admire is Steve Brodner. He’s a freelance caricaturist, and his work is published in every major magazine and in ad campaigns. He’s well known in his field. We used to do parties together, but everybody hated his work because his caricatures were extreme. I loved his work, but the guests at events didn’t like the way they were portrayed. So he gave up the party work to do political caricatures.

An artist can be on dangerous ground doing caricatures because exaggeration is intrinsic to the form. How do you handle the exaggeration?

It’s a difficult area. It’s a fine line to tread. When I started drawing caricatures, I thought I had to exaggerate. But caricature can go from the grotesque to a simple cartoon. I fall in the middle. People like my work because I make them look good. I look for the positive qualities. I don’t exaggerate the features in an extreme way—I could, and if somebody annoyed me by telling me how to draw them, I might. But for the most part, I look at people in a positive light. I enhance their features. People watching me draw say things to the subject like, Your caricature looks more like you than you do, or, Hey, you ought to take this to your plastic surgeon. It’s all in fun, of course.

I didn’t know how to do this when I first started, so I would get into trouble occasionally. Then I became more adept at drawing and reading people. I can tell from looking at somebody whether or not they’re going to have a sense of humor about their caricature. Women do not have a sense of humor about their caricatures at all. I have to make them look good. In general, men have a better sense of humor about themselves, so I take advantage of this and exaggerate more than I would for a woman.

I was doing an event, and a very well-groomed man sat down to get his picture drawn. He was a great subject for a caricature. He had a long face, and he had a big pompadour, and he was dressed in a suit and tie. He was a wonderful subject, but I knew he was going to hate his caricature. I went for it. I could not resist. There are people who are great subjects. He had pushed his way into my line. He wanted to see what I would do. And it’s a wonderful caricature. I have a strong feeling that he hated it. Not exactly his self-image.

Sherry Lane with a guest and her caricature at a Citibank event, 2013.

You mostly do this live—and you say you’re fast.

Five minutes. I’m very fast.

What do you zero in on in a person’s face to start the work?

At this point, it’s a difficult question to answer. I’m looking at the whole face, the personality, and I just start to draw. First of all, I’m in my right brain, my creative mode, and it’s nonverbal, so I’m not analyzing, or saying to myself, I’m going to give this person a big nose. It’s not language that’s going on in my head when I’m looking at a person. I want to capture their personality as well as a likeness. Often people don’t see themselves in the finished drawing. They see their mother, their sister—they see the family resemblance.

You’ve studied face reading, and you practice face reading. I’m wondering how the caricatures and the face readings connect.

Caricature led me into the study. In drawing a caricature, you’ve got to capture the essence of a person. A lot of information about the life of that person comes through the drawing process. That fascinated me, so I started to research the subject. I thought I discovered something. No, I didn’t. There’s a long Western tradition, a long Eastern tradition. As I researched the subject, I discovered a wealth of information, and I began to study physiognomy, the art and science of reading faces.

The Chinese believe in fate, and it was my fate to cross paths with a Chinese man who wrote a book on face reading [Face Reading: The Chinese Art of Physiognomy by Timothy T. Mar]. I found his book, and then I went to a lecture and met him. He started to train me in the art of Chinese face reading. The face is divided into three sections: from the top of the head to the eyebrows, from the eyebrows to the tip of the nose, and, as you age, from the tip of the nose to the bottom of the chin. Reading a face chronologically, I can see that a lot of young people now will live to be 100 years old. Timothy taught me that system, so that’s why I say I can read past, present, and future on the face—and I do. Professionally, I do it as entertainment at parties and special events.

You’ve said you’re not thinking intellectually as you work. Are you understanding the person’s essence instinctually?

Yes, I’m seeing it, but I’m not attaching language to it while I’m drawing. It’s very hard to draw and talk, and I’ve had to learn how to do that. When I first started drawing caricatures, I couldn’t speak. I had a very hard time with that. So I’d sit and draw and smile and pretend I was listening. I had to develop language while I was drawing just to be social. So at different points during the drawing, for example, when I get to the hair, I might chat a little bit, ’cause it’s a more free-flowing line, and I don’t have to be so concentrated. Most of the time, I’m extremely focused, and the information is coming through intuitively. I see the lines and sense the things that reveal personality.

I’ve read that the caricaturist’s skill is to distinguish the private self from the public self, to understand what’s being hidden. Is that what you mean by getting to the essence of the person?

Yes. This recently happened to me, and it was unusual. A woman sat down to get a caricature done. I do start out chatting—What’s your name? What do you like to do?—because I put in a little body with a sport or hobby or interest. And she said to me, “I don’t know. I’m a happy person.” Normally, I don’t do this, but this face was so unhappy—I said, “I don’t think you’re a happy person.” (I’m older now. I wouldn’t have said that when I was younger.) I said, “I don’t really see a happy person.” And she started to get angry, and she took a breath and said, “Well, you’re right.” And I thought, What am I doing? I don’t know this woman from Adam. She’s a guest at a party. But it came up again. She went back, “Well, I’m a very happy person.” And I said, “I don’t think you’re that happy.” She thought she was covering her real emotions and presenting herself as a happy person. So I said, “OK, give me a smile, and I’ll draw you as a happy person.” And she had a horrible smile. I worked on it. I gave her a little smile and softened her features—and she walked away a happy person.

It comes down to the muscles and the fixed expression on the face. The mask. Features get set. And if the features are set, they’re not natural. They’re not real. She sat down with a very set mask on her face. The masks reveal a lot. And that’s what I look at when I’m doing a face reading, all of that information. How is that person sitting down? Are they pleasant? Are they smiling? Are they nervous? All of those things.

Some people have a hard time being photographed.

Yes, it’s the same thing.

But that’s not the essence of the person. That’s the person being uptight about being photographed. How do you get past that?

The same thing happens when I’m going to do a drawing. They react as if they’re going to have their picture taken. Somebody will sit down in front of me, and they’ll smile. They’ve got “the smile.” They can’t hold the smile for five minutes. A smile is a spontaneous moment of happiness. If the smile is held, it gets fixed. It’s not real. So I always say to that person, “You don’t have to hold the smile. Just relax. When I get to the mouth, I’ll ask you for a smile.” Then they relax. When I get to the mouth, I say, “OK, give me that big smile,” and they start laughing, and I can draw a natural smile.

Most artists have some kind of photographic-image ability. All I need is a second. I just need them to flash a smile for a second, and I’ve got a picture of it. It’s like a stop-frame photograph. Every time I look up, I’m taking a picture in my mind. If I look up, and they have a revealing expression on their face, I’ve got that. The fixed expressions that people have reveal their emotions. The natural expressions are spontaneous. In five minutes, I’m drawing, looking, drawing, and looking. Those are snapshots. And that person doesn’t know when I’m coming back to them, so I’m getting a lot of information when they relax, when they’re distracted, when they’re talking to their friends, when they’re looking up. So both the fixed and the natural expressions are being registered—and they are all revealing something about the person.

The Endo Pharmaceuticals group, 2003.

I didn’t realize that you do cartooning, with captions and speech bubbles.

Somehow I got into the world of Wall Street, and they came to me with these group drawings. That’s where I got into creating a little scene, cartoon backgrounds. I don’t do political cartooning. I’ll do the cartoons for the kids, party art, but the more detailed cartooning came into play for the Wall Street companies.

There’s a book about the fall of Lehman Brothers. Vicky Ward wrote it. It’s called The Devil’s Casino [2010]. My caricature is a plate in the center of the book. The publisher came to me. There wasn’t a photograph taken of the inner sanctum with all the top brass at Lehman Brothers. There were some separate photographs, but not one of everybody. And I had done a caricature of the group in the late eighties.

Lehman Brothers had come to me and said, We want a group caricature. We have our lunch meetings in the executive dining room, and we want a group caricature of that. They invited me to Lehman Brothers and set me up in an office. They couldn’t all sit at once, and I couldn’t take a picture. They were very busy, and they were all big shots. So they came in one at a time, and however they sat at the desk across from me, that’s how I drew them. I did the head and shoulders of each one of them separately, then created a composite of the group. Also, they wanted their dining room exactly as it was, what it looked like, what they ate, the plates, the silverware, the setting. They wanted everything to look the way it did every week when they had this lunch meeting together. After I drew each one, they took me into their private dining room. It wasn’t that big, but it had a big oval table. I sat at the head of the table, and I spent the next couple of hours drawing the table, the room. And the staff came in and set the table so I could include the dishes that were typically served. They set the plates and the silverware. And then they brought the food, the exact dishes that the guys would eat at lunch. It was very modest, like tuna salad and egg salad and chicken salad. I did it in color, but in the book, it’s in black and white. I read the book, and it’s the only picture of the group together. So while you’re reading the book and reading the names, you refer back to this caricature.

Do you do the other corporate compositions in a similar way?

No. Most of the Wall Street work is done through photographs. They email them to me. It’s all done on the Internet. We work out a theme—and I know from experience that they’ve all got to have a special place in the drawing. I have to ask, Who goes with whom and where? I’ve run into the problem of doing a complete caricature for a major company, and the CEO was put on the side. Once I did a caricature, a cast of characters, and they were on a yacht, fishing. I didn’t have the CEO of the company as captain. I had to do the entire drawing over.

JPMorgan’s is a good example of how I work these out. The setup is an outer space theme. So I have to piece everything together, all the different scenarios. These three have to go together, and these guys are mission control, and these are the girls in the office. It’s like piecing a puzzle together. I start out with blocking in groups and ideas, and somehow I bunch them together in what looks like a theme, and the drawing has a flow.

The JPMorgan group, 2005.

How do you feel about working from photographs? You’ve described what happens in the live experience. But with these corporate compositions, you’re removed.

Very much removed. I lose a lot by working from a photograph. A lot of these photographs are small snaps of people or their company-ID photos, so a lot is lost. For example, someone from the company will come back to me and say, Well, so-and-so doesn’t look exactly like that. And I have to ask them to get me a better and more recent picture. That’s all I have to go on. I run into that all the time with photographs.

Do you find the live experience more gratifying as an artist?

I prefer to work live. I prefer to go out and do a party. You work up a rhythm. You start out a little bit slow, and then you move into the zone, and the time disappears. Everything disappears, and you’re in this rhythm of drawing. It’s fun and challenging, and interesting things come out of it. I enjoy that the best. When I get one of these group-composition projects, they’re a lot of work. I’ve got to set up the drawing board. I have to work all alone, and I have to be very disciplined. It takes energy and effort to sit down and get the job done. But I get satisfaction out of taking all these pieces and turning them into something coherent. I like the final result.

“Stormin’ Norman” and the Gulf War, 1991.

I noticed on your website that you’ve done a series of political figures. And you send the caricature to the person.

I didn’t do a lot of that, but the few that I did do were really fun. I picked people I had an interest in. The Persian Gulf War in the early nineties was a big deal. It was on TV all the time, and I got hooked watching. It was shocking at the time. I got to know General Norman Schwarzkopf from watching the coverage. I thought I would do the caricature while I was watching the TV. That’s how that evolved. Plus it never hurts to have some samples for my portfolio. Once I did it, I thought, I’ll send it.

Hillary and Bill Clinton, 1993.

And the subjects sent a note back to you.

That was all a surprise. Hillary Clinton, I’ve met. Our paths have crossed on a number of occasions. I did that postcard of Bill and Hillary from a photo. One time I was at an event, and Hillary was giving a talk, and we were sharing the same “dressing room.” (It was an empty ballroom.) I had that postcard in my briefcase, and I gave her the card. My political cartooning is just happenchance.

You worked for Star magazine. What did you do for them?

That was in the eighties. I had a regular feature, and I illustrated a column by Mary Ellen. She did helpful hints. Every week I would do the illustration and put her in it with a saying in a speech bubble. I loved it. It was also a discipline. I had to produce every week. I like that, though. It was challenging, too, to come up with a new idea—here’s the column, and then do something with that.

You call yourself an entertainer. Would you talk about the intersection of your entertainment work and your artwork?

I feel that what I do is entertainment. I feel that’s such an important part of drawing caricatures—making people laugh and having fun with them and keeping the momentum going. You have to be an entertainer as well. You’re hired, and you’re there to make the guests feel comfortable and have fun—and to want to get their caricature done as part of the entertainment of the evening. That’s why, as I got more experienced, I moved away from the grotesque to more middle of the road, where I’ll tend to enhance the features rather than exaggerate them.

Over the years, you’ve become quite an entrepreneur. I have your postcard listing the entertainments you offer. Plus you have a whole team.

The entertainment company came out of the overflow of work. Over the years, as my business expanded, I got into booking other people who do interesting things. First it was other caricaturists. I had a little caricaturists collective. There were four of us, and Steve Brodner was one of them. Then it expanded to include Sam Norkin. So as my business expanded, and people called for me, I would say, I’m not available, but I can get somebody for you. Then that business grew to include a magician, a face painter, a stilt walker. I still have my college clients. The Fashion Institute of Technology is a regular client. They call me to book novelty performers. I’ve also got a henna tattoo artist, a strolling magician, palmists, tarot card readers. I’ve worked with FIT for about twenty years. For Christmas, I hired a Santa for them, a real Santa with a real beard.

A real Santa?

Last year he corrected me because I called him Frank. He changed his name legally to Santa Claus and upped his fee. He bought a cashmere Santa Claus suit. The white trim on his suit is fox. He got a leather maker to make his belt. They love him. He’s a great Santa Claus. I book events for FIT. I bring talent into Fordham. I do a couple of events for them every year. And I do corporate events. In fact, most of my business became corporate—Estée Lauder, Avon, American Express, the Wall Street guys. When the recession hit, they just went under cover. They don’t want to spend money. They don’t want to look like they’re spending money. My whole industry changed. Everything changed. I’m still doing what I do, but it’s different.

I ran into you on the street one day, and you were going to be reading tea leaves at the Tenement Museum.

I do whatever they ask me to. Last night I was doing palm reading.

I remember when you were reading palms and tarot cards for your friends. You’re the best tarot card reader I’ve ever met. Just as you do with your caricatures, you put a positive spin on the readings.

Absolutely. With the caricatures, with the readings, no matter what I’m doing, when people get up from a reading, they feel better than when they sat down. I think that’s a great gift. If I can do that for somebody, I feel really good about it. Even if sometimes I say something that’s not so great, I try to finish on an upbeat note.

All caricatures by Sherry Lane. Courtesy Sherry Lane.
(To see more of Lane’s artwork, go to

Profiles in Art, Copyright 2013 Terry Stoller and Westbeth Artists Residents Council

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