Blast from the past!

Caricature T-shirt for my high school basketball team’s fundraiser.

I think I did 7–10 of these when I was in high school.

Becoming a caricature artist

Back in the day (~20+ years ago), I was a caricature artist. I lived near the Cedar Point theme park in Sandusky, Ohio and one day Kaman’s Art Shoppe that runs probably most of the caricature/portrait booths at major theme parks, came recruiting at my high school for more artists. I was a freshman at the time and I was really familiar with caricatures at Cedar Point as my family had a season pass most years. I remember the year before when I was in junior high (so probably 13 years old) I brought in my portfolio to show the artists there and asked for tips on how to get a job there. I was big into Marvel comics/art and portraits at the time and they said I had potential. So when they came recruiting at my high school I immediately requested an interview!

I was 14 years old so Mom had to drive me to my interview. LOL :) I had to draw a caricature and a portrait and pretend to sell a pencil to them so they could see if I had any sales skills. Lucky for me they accepted me and I got to attend a little boot camp. My boss and mentor (I can’t remember his name!!) was incredible and patient with me as I was so young. He gave me exercises to do and drills to practice. He explained how to use the materials and what to focus on when looking at different people’s features and also things to pick up from their demeanor. It was a pretty incredible experience when I think back on it. I was only 14 but I was tall for my age, 5’ 7”, so as long as I tried to act mature I don’t think anyone discounted me for being so young.

Going freelance

So after a summer of working at Cedar Point, my enterprising Mom convinced me that perhaps I should just go my own way and not work the grueling hours at the park. Park hours are LONG and you stand all day on blacktop in the heat in the middle of summer, sometimes not under a tent. I was also into tennis at the time so being a freelance artist allowed for me to take more tennis lessons as I would then have a flexible schedule. I still didn’t have my drivers license so Mom dedicated her summer to driving me to different places to set up shop and chaperone me. I drew at the Toledo Mall near the food court, at local bars (which was hilarious as some of my teachers were there drinking), at birthday parties, etc. I was also approached by my high school to draw sports team fundraiser caricature T-shirts which I’ll focus on now. :)

Caricature fundraiser T-shirts

The group that approached me was called DECA. It’s a high school organization focusing on business skills and entrepreneurialism. They crafted an idea to raise money for the school and I think they also “competed” on the idea within the DECA organization. They said, “We want you to draw the varsity boys basketball team and we’ll put the image on a T-shirt. We’ll give you two bucks per shirt.” Which was sweet! Just make one picture and put it on some merchandise and sell it. Jumping ahead, I think I ended up doing 7–10? projects like this with them throughout my time in high school. The projects raised over $18,000 for them (our town’s newspaper did an article on it at the time). I don’t remember how much I got for my cut in total but it was pretty good for high school money.

Challenges of creating the shirts

So ultimately creating these fundraiser shirts was a big hit but creating them had it’s challenges.

  • Getting pictures of who you are drawing. Luckily the DECA group organized the accumulation of all the pictures of the players and their numbers and all that but I do remember that was a constant struggle. You really need someone dedicated to making sure you know how many people you are drawing (all the coaches? select members of the jv team? someone on the bench that helps with stats?) before you even get started so you can then space everyone within the picture.

    • Ways around this issue: These days with digital art, you could technically draw each person individually and then place them in a pleasing composition in the picture but that wasn’t an option for me at the time. Also, as I prefer the look of traditional artwork this will still continue to be a challenge if I ever work on a project like this again.

  • Fonts. Fonts, who knew?? Text on your picture brings its own set of challenges. Did you know that the fancy fonts require licenses and working on joint projects you need special licenses (and $$) to achieve a certain look?

    • Ways around this issue: I started to opt for hand-drawn words over time.

  • Approvals. Luckily, I didn’t really have to deal with people approving my artwork. For the most part people trusted that I would get a good resemblance. However, there were a few times as a caricature artist at the park where someone would request that you redraw them or make edits. As you need to draw with dark ink for a good print this causes an issue when working as ink is not erasable and drawing the picture gets more and more stressful toward the end of the project; if you mess up on someone you don’t want to redraw everyone again!

    • Ways around this issue: Consider working digitally so you can erase the ink, or at least hand ink each person individually so if one person doesn’t like their picture you don’t have to redraw everyone else too. Or, explore using white gouache to “white-out” over a bad ink job.

  • Weird financials from working with a nonprofit like a PTA (parent teacher association) or basketball team. Luckily I didn’t have to deal with any of that, DECA took care of the money/tax aspects and just paid me a chunk of each shirt.

    • Ways around this issue: Go see a real accountant and pay up :-o

  • Lower margins from too much color. In retrospect, I probably didn’t need to color in everyone in the picture as when you are silk screening, each new color you introduce into the picture costs extra money. I think all my pictures were four color images… black/red/brown/yellow/and possibly a blend of those colors for tan (although I never inquired too much about what the print shop was actually doing to achieve the colors). Yes, coloring in skin and hair can help you identify the members of the team from each other quicker, but if you have a good resemblance of facial features, hair, and their jersey number you should be fine.

    • Ways around this issue: Consider NOT coloring the people, showing their jersey number, and consider black and white illustrations on a colored T-shirt. Or, if you do color the people, perhaps consider using one color for everything and just using different values for a monotone look.

In conclusion…

You can probably tell I’m musing over doing this again… but it’s been 20(!!!) years since I did it so if anybody else reads this I’d say go for it: it’s really enjoyable but with a few different issues you have to work through to make the project a success.

But I consider it a really unique fundraiser:

  • It’s a custom keepsake and time capsule. Who doesn’t want a momento of their kid: a drawing of them with the year it was drawn and different kids they were hanging out with at the time?

  • This fundraising item lasts. It’s also apparel unlike some other fundraisers like cookie dough which you eat (or don’t) and it’s gone forever.

  • You can raise a decent amount of money with it.

  • You can support your local T-shirt print shop and local artist.

:)

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