About Ray Drea

Creating art is a gift and passion that I’ve had since about six years old. That’s when I first started to get the encouragement and affirmation of others.

I was number 7 of 8 kids. Ma Drea had her hands full. She redirected all our energy to sit us down at the kitchen table for a time-out. (I spent a lot of time there as a kid.) With a box of crayons, the time flew by, and that was the beginning of my “disciplined” art training!

My automotive/motorcycle custom painting career began at 12 years old. My curiosity and perseverance in this profession opened my eyes to various mixed media and skills: airbrush, pinstriping, lettering, gold leaf, spray painting candy and pearl over entire cars and brushing acrylics for detailed murals.

After graduating from high school, I set my sights on teaching myself graphic design. This was before computers when everything was hand-drawn. I grew quite a business creating everything from elaborate t-shirt designs for the hot rod industry to compelling corporate brand identity for major brands in the US.

While still in high school some of my design work caught the eye of Willie G. Davidson, head of Styling for Harley-Davidson. I did a lot of graphic design for Willie and in 1993 he asked me to join the Motor Company. I worked in Styling the entire time and later took over when he retired.

I learned so much about art & design living in the corporate world for so many years. I got to live my dream of being a steward of this respected brand that I first fell in love with as a little kid on the back of my oldest brother’s Harley while getting a ride around the block.

In 2020 I retired from H-D, leaving the corporate world to get back to my independent roots.

My reward for working at H-D was the scalability of producing art. When you designed something special you were putting smiles on thousands of faces around the world – an awesome feeling!

I missed creating one piece of art for one person at a time. Making that personal connection through the collaborative process of commissioned art, and knowing you hit a bullseye by witnessing their joy, is really what sharing my gift is all about.

Feeling fortunate because of the great opportunities I’ve had in the profession/medium of pinstriping particularly, I wanted to give back. In 2003 I co-founded Pinstripe Legends to increase the awareness of pinstriping as a fine art form. This is an organization of pinstriping artists from around the world that travel to Milwaukee each year to paint work to be auctioned off for an entire weekend. To date, the group has raised just shy of one million dollars for Children’s Hospital of Wisconsin. At the show, we honor one artist each year with a lifetime achievement award.

I’m currently in Delafield, WI with the girl of my dreams of 27 years – my wife Mary. We live in a beautiful Lake Country area that provides the space and inspiration for this artist to get lost in his work. We have two adult sons, John and Will, that stop by to check on us and provide an update on their latest creative endeavors. Really, I think they are just coming by to see how our family dog Ginger is doing.

I am very blessed to be surrounded by many people in my life that saw my raw talent and gave me opportunities to demonstrate and hone my talent while also giving something back to the viewer. I would call that a win-win!…and that is what continues to motivate me every day and fuel my soul.

Thank you to Michael Lichter Photography for the cool pictures of me and my art!