The Story behind the T-shirt: The Freewheelin’ Bob Dylan (Part 2)

Ever since I began to design the stamps for IloveWaterloo T-shirts, I have created a big list of “essential” artists to dedicate a T-shirt. Bob Dylan always had a priviledged position in that list.

I always loved the cover photo of The Freewheelin’ album. When I finally decided to make a T-shirt of Good Ol’ Bob, this was the first image that came to my mind.

To adapt this very famous image, I decided to re-create it my way, and I thought of make a drawing with pencils, watercolors and finepens. I had never used this technique in any of Waterloo’s T-shirts, but this was a character that deserved this kind of challenge. One of things that I most admire from Dylan is his capacity for surprise. That’s why the idea of making a T-shirt with a watercolor drawing seemed to fit perfectly in this case, because it was going to be very different from the others.

To begin with, I printed the image cover in a big size. I put the record on, sticked the printed image in the window of my house and made a trace of the shapes and buildings as a guide. I made the most of a pretty sunny morning to draw with daylight. I finished the strokes with pencil and then I started working with the watercolors.

It was not easy to paint with watercolors, especially for me, because I have never learned how to use them; I always improvised. In musical terms, it could be said that the first take was the best one. I painted and I left the drawing to dry near the window.

By the afternoon, the drawing was dry and I was pretty satisfied with it. I re-marked with a black finepen the pencil strokes to make them stronger.

Then I had to decide what to do with the texts of the cover. I want them to be in the drawing howsoever it may take. I tried to add them with Illustrator, using pre-existing tipographic fonts that were similar to the ones in the album cover. However, the coexistence between computer words and a watercolor drawing was not good, so I decided to adapt the texts too. I drawed the title and I found it pretty good, although I didn’t thought too much about it, I liked it to be something spontaneous.


For the song titles I tested some alternatives without any successful result. So the following day I showed to an old friend from work all what I’ve done so far. She picked the drawing and the album cover and began writing the song titles in a sheet of paper. I liked her writing style and the way it combined with the album title made by myself. That’s how this piece was finalised, after being scanned and has some color adjustments done with Photoshop. This was my graphic tribute to the great Bob Dylan.