Drawing Cyndi Lauper: A Visual Blog

Drawing Cyndi Lauper

Illustrations © Susy Pilgrim Waters

"Can you draw a portrait of Cyndi Lauper in your ‘Susy way’?” asked Live Happy Creative Director Kathryn Finney. I would love to, was my immediate response.

But I only had a short window to do it in as I was off to London. The quick deadline did not turn out to be a problem, however. Kathryn and I have worked together many times before. She knows my work well, and she understands that when I get an assignment I’m excited about, I attack it with relish—like a dog with a bone!

Kathryn sent me some pictures of Cyndi for reference and I started to do research. I listened to her new album, Detour, and I began to connect some dots.

My visual impression was she still loves black with plenty of full-bodied reds and pinks. I would use a monochromatic or limited color palette. I could draw her head-on or full body….She certainly still looks great. One thing I knew for sure—I would focus on her joie de vivre.

Below are some visual sketches I made that will give you a sense of my thought process. To see the final illustrations and read the feature on Cyndi, pick up the latest issue of Live Happy magazine at a newsstand near you, or come back to Livehappy.com in a couple of weeks.


Susy Pilgrim Waters is a highly accomplished illustrator, painter and graphic designer. She grew up in England and has done work for clients all over the world.

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