Q:  What advice would you have for someone thinking about getting into live caricature? I’ve been doing them for about 3 years now but still have much to learn. It started out as something I did for fun/practice and lately I have been selling them. The thing is I’m used to having a lot of time, often times days to find a person’s likeness, color, etc, drawing and redrawing until I’m satisfied. Usually in illustrator/photoshop but also paper on occasion.  How do I know when I’m ready to go live? Is there a way to get my feet wet first before diving in head first?

A: Unfortunately the only way to learn to do live caricatures is to do it. No amount of reading or practicing from photos will really prepare you for drawing live. It’s a catch 22 because you can’t get the hang of live work without drawing live, and you can’t (or rather shouldn’t) start drawing live as a professional until you get the hang of it. It’s something you have to develop an eye and instinct for, and no amount of studying will accomplish that.

With new artists that work with us at our theme park operations, I or one of my artist/managers spend about two days working with them, teaching them theory, techniques and that kind of thing. They get to draw the other new artists for practice and to try out the things they have learned. Then they spend the next week or so doing practice live drawings from volunteer theme park visitors who are willing to sit for 10 minutes or so knowing the drawing is just for practice (they don’t get to keep the drawing unless they want to pay for it, however). I estimate they have to do about 100 live caricatures over 4-5 days before their lines and the confidence in them gets to the point where they are doing a “sellable” drawing. Then they can start doing them for money and continue to develop their abilities as they move forward.

It’s easy at the theme park, because there are always people coming by who are willing to be a guinea pig for a rookie caricaturist, so there is a constant flow of volunteers for practice. On your own it’s not so easy. My suggestion is to volunteer to draw at charity events about town, at local schools at their homecoming or other events, or just set up in conjunction with some festival or fair… anywhere there is going to be a crowd of people. Even at the local park or mall will work, but it’s best to align yourself with some specific event or charity so you have an excuse for giving them away. Then get as many drawings under your belt as you can, drawing them in the way you want to do your live work. After half a dozen of these events, you will get comfortable and confident, and your instincts and eye will begin to develop.

If you want to know the absolutely best way to learn to do live caricatures, get a summer job at the nearest theme park caricature operation. As long as the owner actually spends time preparing you to draw live, you’ll have a chance to learn a few things and then 3 months of boot camp-like constant drawing develops your skills like no other experience does. By the end of a summer of theme park caricatures, your drawings will be light-years ahead of where they were at the beginning. Not everyone can just drop their lives and do something like that, but it is an ideal way to do it.

Thanks to Kyle Maloney for the question. If you have a question you want answered for the mailbag about cartooning, illustration, MAD Magazine, caricature or similar, e-mail me and I’ll try and answer it here!

Q: Hey, Tom, I’m a daily reader of your blog and would like to hear you talk about getting started, i.e. your first steps into the cartooning field.

A: I can certainly tell the story of how I got started in cartoning but it wouldn’t apply much to today’s market. Circumstances change with time and what was true then is no longer true now, just as breaking into the cartooning field in the 60′s was different than it was when I did it in the late 80′s.

I went to college at a small art school called the School of Associated Arts in St. Paul, MN, where there was zero cartooning in the curriculum. I was on my own when it came to learning cartooning or incorporating it into my career plans. What made an eventual cartooning career possible for me was getting a summer job doing caricatures at a theme park near Chicago, IL. I worked with some very talented cartoonists and artists, including illustrator Gary Fasen, current DC Comic’s superstar Doug Mahnke, WB animator and children’s book illustrator Dave Kamish and many others who went on to have successful art and cartooning careers. I learned a lot about cartooning, caricature and humorous illustration working with those artists and applied what I’d learned to my schooling where and when I could. My first freelance cartooning job was doing caricatures for a morning radio show advertisement that I did for one of my college professors who had a design firm.

In 1989 went on to manage a caricature art concession at Six Flags, Atlanta for Fasen Arts, and while there I “broke” into cartooning via a comic book company called NOW Comics. One of my fellow caricaturists, Chuck Senties, had gotten a job drawing a title called Ralph Snart for NOW, and had let me know they were looking for an artist to draw another title for them called Married… With Children. I sent them some sample pages and became the penciler on the book.

That was really my first big break in the field, but it was a combination of luck and circumstance. The luck was hearing about it and applying at a time they were looking for an artist capable of humorous comic book work and caricature. The circumstances which made it possible were several. First, in 1989-90 the comic book field was in a golden age where comic books sold by the millions of copies and almost anybody who could breathe and draw even a little bit could get a job in comics. Second, NOW Comics had a bad reputation for not paying or paying late, and no one with any real experience wanted to work for them. Third, in the meantime I opened up my own caricature concession operation at Underground Atlanta and had that and my Six Flags jobs to pay my bills so I did not care much about that second point.

Anna and I, and our baby daughter, moved back to Minnesota in 1990 and I opened up another caricature concession at a small theme park called Valleyfair. I was still doing Married… with Children and did a miniseries for Marvel called The Coneheads as well, and I also started to pursue other freelance work by showing my portfolio around the Twin Cities and talking to other illustrators. I got a few local jobs for publications like Minneapolis/ St. Paul and Twin Cities Business magazines, but quickly realized the local market was too small for me to make a go of it with freelance. I started advertising in a source book called the Directory of Illustration, a nationally distributed illustration ad book. I didn’t get many clients from that ad, but I did get a few that gave me a lot of work, chiefly among them Business and Legal Reports where I did several comic book style booklets for school distribution on anti-smoking/drinking/drugs and similar themes. This client wanted digital files so I was forced to learn to use the computer for my work, something I had not ever done before. That would prove important.

Each year I continued to build my freelance clientèle slowly, adding a few new clients each year and gradually building my income from freelance up over time. I also added caricature operations in Missouri, Louisiana and Massachusetts along the way. A few jobs doing the images for some humorous CD-ROM games from Parotty Interactive and Hasbro got me deeper into the computer illustration end of things. Some more high-profile clients like Time Digital, National Geographic World, Detour, General Mills, Broadcasting and Cable and several pro sports team magazines helped increase my visibility. Continued advertisement in the DOI source book would get me a few new jobs and one or two new clients a year.

Eventually I got serious about working for MAD, and pursued that for about a year before they acquiesced and gave me a few assignments. It’s hard to believe but it was eight years ago next month I got my first MAD assignment. Since then MAD has been a steady client (among others) and many other clients have come and gone. Freelancing is both a blessing and a curse.

Two things were crucial in giving me the means and tools to eventually make a living as a freelance cartoonist / illustrator.

The first was the caricature art concession businesses I at first worked for and then my own that I started up and ran. That experience at first exposed me to some talented and knowledgeable cartoonists from whom I learned a great deal and through that job I developed my caricature and cartooning skills far more than I would have in art school. Opening my own businesses doing caricatures allowed me the financial freedom to pursue my freelance career at my own pace, not having to worry about house or car payments, or buying shoes for my kids. Without that, I’d have had to resort to a “day job” and likely would never have been able to keep at the freelance thing long enough to make a go of it.

The second element was my being forced to incorporate the computer into my work. Fortunately I was fascinated enough with the computer to take the time and put the thought into how to make the computer work for me in order to accomplish what I needed to with my commercial work. There is no question that the coloring techniques and digital delivery that is a part of most of my work today got me more than a few jobs over the years.

Thanks to Philip Wiley or the question. If you have a question you want answered for the mailbag about cartooning, illustration, MAD Magazine, caricature or similar, e-mail me and I’ll try and answer it here.