A Midwest Caricaturist in King Alfred’s Court

August 15th, 2013 | Posted in Freelancing

…or “A Theme Park Caricaturist’s Long Journey Down a Freelance Path”

The following is an article I wrote for the latest issue of the International Society of Caricature Artist‘s quarterly magazine Exaggerated Features. It is one of a series they call “A Master Piece”, meaning articles written by past winners of their highest honor, “Caricaturist of the Year” aka the “Golden Nosey” (which I won in 1998 and 1999). Its focus is advice on ways a live caricaturist can branch out into a career in freelance illustration:

I’ll never forget my first summer drawing caricatures. It was 1985 and I was a new artist for Fasen Arts at Six Flags Great America in Gurnee, IL. Madonna was the newest pop star, Arnold Schwarzenegger was a budding action movie hero and people would immediately recognize a sample of Grace Jones hanging on the wall. I had just turned 19, and was getting paid to draw. Paid. Real money (sort of). I spent that summer thinking, in my best stereotypical Italian cartoon voice, “Thees eesa da life!”

I enjoyed doing live caricature. I must have…I did it full time for over 20 years. I found it challenging in its unique dynamic which demanded a combination of speed, accuracy, and interaction with the subject, all the while in front of an audience. After a while, however, I got a little tired of watching all my work being carried away in a rolled up tube bag or a cheap frame destined for the wall of someone’s basement rec room, or on a refrigerator via a magnet shaped like an ear of corn, or some dusty junk drawer. I knew live caricature was always going to be some part of my career as an artist, but I also wanted to branch out and see if I could become an illustrator doing comics, cartoons, advertising, magazine illustration . . . wherever “humorous illustration” was needed. I wanted to be a freelance illustrator…I just needed to know where to begin.

I get a kick out of people who seem to think you get “discovered” as an illustrator and that overnight you go from doing art for your local church social to TIME magazine covers. That happens to no one. A freelance career is something you have to develop over the course of many years, slowly building a client base while tirelessly pursuing jobs. Developing that freelance career takes a combination of hard work, perseverance, determination, fearlessness in the face of failure, and a bit of luck. By the way, that last one isn’t totally out of your control…luck is something you make for yourself. Luck in freelancing is simply having your work on the desk of an art director right at a time when they are thinking they need an illustrator with your set of skills for a job. The previous four elements of building that freelance career set up that fifth one… you make the luck.

The most valuable piece of advice I ever got about freelancing came from the great caricature illustrator David Levine, and he told it to me in that timeless repository of all wisdom and great thoughts: the restroom. It was 2000 and I was then president of the NCN (the former name of ISCA) and had organized a mini-con around a panel presentation on caricature taking place in Minneapolis as part of the American Association of Editorial Cartoonists convention. In addition to David, the panel also contained Philip Burke, David Cowles and Steve Brodner (I think Steve was there, although he might have not made it), moderated by Bob Staake. About 20 NCN members were in the audience thanks to a special fee that local host and editorial cartoonist Steve Sack got for us just for the panel. It was enlightening, not surprising given the talent on the stage.

After the program I was in the hotel lobby bathroom when Mr. Levine entered and came up to the urinal next to me. We were observing the male ritual of staring straight ahead into the tiles while engaging in small talk as we relieved ourselves. He told me he noticed I had asked several good questions on freelancing.

“Do you want to know the real secret to a successful career in freelance illustration?” He asked.

“Uh…. yes!” I replied.

“People,” He said. “That’s the key to making a living and being successful as a freelance illustrator. It’s all about people and building relationships with people.” He went on to say that doing good work was what got you your first few jobs, but continuing jobs was about building relationships of trust and respect with art directors, because they invariably moved on to other art director jobs and passed your name on to other ADs, who would give you jobs and then you’d build a relationship with them, eventually creating a large web of contacts and people who know you were a professional who did not only good work but who did it in the professional manner they appreciated. That was some great advice and I have built my career around it.

As we were flushing and zipping up, he commented: “Shithouse wisdom… it’s the best kind.” I agree.

Not that just “knowing people” alone will get you very far. The ability to do good, eye-catching work that has an appeal to art directors is the first order of business. Many live caricaturists are great at doing a single caricature of a subject, but their comfort level stops at the neck. Caricature is one of those skills that is “evergreen” in the world of illustration, meaning it does not go out of style. When you get right down to in, most stories, articles, books, shows and other media are about people, and caricature is a unique and entertaining way to depict people that is much more than just photography. As a result, caricatures are something that work for almost any facet of media communication at some time or another, and are always in demand. The popularity of styles come and go, but caricature as an element of illustration is here to stay. That means illustrators that can do good caricature can always find outlets for their work.

Notice I said “illustrators that can do caricature” as opposed to just “caricaturists”. That’s because when you are talking about illustration, it’s more than just from the neck up. You have to go beyond doing just a caricature of your subject’s face . . . you have to caricature the whole universe. One of the greatest humorous illustrators of all time, Jack Davis, is a prefect example of this. Jack’s caricatures and drawings of people are instantly recognizable…but so are his drawings of everything else. A Jack Davis fire hydrant is unmistakable as his work. Likewise a Jack Davis chair, or fishing boat, or telephone, or ham sandwich . . . Jack’s art shows us the universe thorough his eyes, all aspects of it. Virtually all great humorous illustrators share this talent: Mort Drucker, Arnold Roth, Jules Fieffer, Sergio Aragon?¬©s, the list goes on and on. That is one lesson I learned early on, that caricature is only a single element in an illustration, and other elements need the same amount of attention as I would give the caricature.

My freelance path reads like a textbook guide for how to start small and slowly build a career doing illustration. I started when I was still in college in the late 1980’s, doing a few small jobs for some of the professors at my school who were also art directors for ad agencies and design firms, and local art like kids menus for area restaurants. In 1990 I got work from a small comic book company called NOW Comics doing a title called “Married… with Children”, which eventually led to a mini series for Marvel called “The Coneheads” in 1994. I did my first magazine illustration for a local publication called MPLS ST. PAUL magazine in 1991, which led to my doing work for the Minnesota Twins when that art director moved over to do the Twins magazine (the Levine Principal in action). In 1993 I did some of my first advertising work when I picked up the ball from another artist who was not getting the job done on a promotional anti-drugs comic book for kids for a company called Business and Legal Reports. I ended up doing 6 more comic book projects for them that were messages about the inadvisability of smoking, drinking, bullying, etc for grade school aged kids. That work led to work for kids magazines like Scholastic, and National Geographic for Kids magazines. In 1997 I did art for a series of CD-ROM parody games for a small company called Parotty Interactive, which led to a big job doing a game for Hasbro called “Super Scattergories”. In 1999 I started doing work for Cracked Magazine, a now-defunct MAD rip-off, doing TV and movie parodies. In 2000, I was in my first issue of MAD. My work in MAD has led to many opportunities over the last 13 years. My “overnight success” took 15 years or hard work and building, and it’s still ongoing after 28 years.

I’ve been lucky, but there have been many, many more unlucky moments overcome than lucky ones taken advantage of. During that first 15 years I sent out innumerable postcards and tear sheet promos, invested in ad pages in Sourcebooks like the Directory of Illustration, and scoured the news stands looking at what kind of artwork different publications were using and which might be most interested in my style of illustration, then adding them to my mailing list. One key ingredient: I used the financial bedrock of my live caricature work to pay the bills when I was struggling to find steady freelance work. Most illustrators have to have a “day job” for a long while until they get that client base built up, I was lucky my day job was still being an artist. That gave me not only time to find and develop those client relationships that David Levine later advised me about, but to develop my skills as well and become a better illustrator. Without my live caricature work and experience, I’d not have ever made it as a freelancer.

Today’s world of publication may be shrinking, but it’s far from dead. There is plenty of work out there, especially for illustrators who are adept at caricature. So far no one has written a computer program that can create a caricature…you still need and artist to do that. While some of the larger magazines are struggling, there are still hundreds and hundreds of niche publications out there with small to medium circulations that need illustrations for their articles. It’s the dirty little secret of freelance illustrators that no one earns a living doing TIME covers. Most illustrators, even the big names like Payne, Brodner, Burke, etc. make a living doing work for magazines you’ve probably never heard of like Snow Country (winter sports), Detour (fashion/pop culture), Broadcasting and Cable (TV/cable industry), UTNE Reader (politics/opinion), Financial Planning (accounting industry) or Contingencies (actuary industry). . . I’ve worked for all those and many more you would not recognize. They pay decently and there are a lot more of them than there are TIME, People or MAD. TV/film, advertising, products and the internet aren’t going anywhere, and there are clients in those areas of media who need illustration as well, especially caricatures.

For those who want to branch out into publication illustration, tomorrow is never as good a time to do so than today. Put together a nice collection of your most appealing work, start looking around your area for companies and potential clients who might be looking for artwork, and start pounding the pavement. The children’s menu you design and illustrate for the corner family diner is the first step on a path that might lead to that fabled TIME cover. You’ll never know until you step onto the path.


  1. Pearls of wisdom in this piece – must-reading for any brave
    soul willing to attempt this weird business of ‘drawlin’ funny
    pichars’ for a living… I forget who said this to me, but I
    thought I’d share it – it’s a supposed actual conversation between
    a wanna be and an experienced cartoonist, possibly a gag
    cartoonist, it goes something like this, circa 1978 I think: Young
    Newbie – “So, can I actually make a living drawing cartoons?”
    Grizzled Veteran – “No, not really, not like in the old days…”
    Young Newbie – “Could I make like, 50, maybe $70,000? Is that
    possible?” Grizzled Veteran – “Oh, you can make $70,000 EASY!
    Anyone can do that…”


New profile pic courtesy of my self-caricature for the Scott Maiko penned article “Gotcha! Mug Shots of Common (but Despicable) Criminals” from MAD 550

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