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.

The Story behind the T-shirt: The Freewheelin’ Bob Dylan (Part 1)

One of our T-shirts is dedicated to the great genius of Bob Dylan and one of his masterpieces, The Freewheelin’, his second album, which was also his big breakthrough, with songs like “Masters Of War” “A Hard Rain’s A-Gonna Fall” and, of course, “Blowin’ In The Wind”. The album cover is one of the best in rock history and our T-shirt stamp is an adaptation of the cover, a drawing painted with watercolors and finepens. But… what’s the story behind the album cover?

To begin with, the cover picture -taken by CBS staff photographer Don Hunstein- presents a young Dylan (he was only 22) walking through a corridor of parked cars and tallish buildings laced with fire escapes along with her girlfriend of those days, Suze Rotolo. The photo was taken in Greenwich Village, in the corner of Jones Street and West 4th Street, just a few steps from the apartment they shared. They are both walking to the camera; Bob looks shy and nervous, and gazes at his shoes, while Suze, attractive and thoughtful looking, smiles and looks to the camera. They look like a happy couple; they were, in fact, deeply in love around those days, and it is said that some of the love songs Dylan wrote for this album (“Don’t Think Twice, It’s Alright”, “Down The Highway”) were inspired by this relationship. However, they have met some months ago (when Bob was 20 and Suze 17), and they would separate soon; this photo was taken after Suze’s six-month trip to Italy. Bob was affected by her sudden absence and, when she returned, things would never be the same: he would soon leave her and fall into Joan Baez’s arms. Nevertheless, this photo captures the instant moment of a man who was about to become a legend, and is one of rock`s best album covers.

The circumstances behind the shoot are described by Rotolo in a book that was recently published: A Freewheelin' Time: A Memoir of Greenwich Village in the Sixties. The cover of the book is, not surprisingly, this famous photo too.

Coming soon: the next post, Part 2, will feature a detailed description of how our Freewheelin’ Bob Dylan T-shirt was created.