Looking at reference photos, I start with a very rough sketch, trying to quickly identify the subject’s most distinctive features. In this case, I noted Roberto Bolaño’s narrow face, round chin, messy hair, and large, circular glasses. It’s not important that everything is right at this stage—I just want to get a quick impression down on paper.

Next, I lay a sheet of tracing paper over my rough sketch and, still looking at reference photos, make a tight pencil drawing. While I’ve tried to clarify his features and proportions, some details still aren’t right—for example, his glasses are crooked. These problems will be easy to fix in the next step, though.

At this point, a real artist would lay down a new sheet of tracing paper and redraw the image with brush and ink. I’m content to cheat however, so I scan the drawing in and recreate the linework digitally. At this point I try to be faithful to the pencil drawing, but I’ve started to make some corrections, including straightening out Bolaño’s glasses. (On the computer, it’s as easy as clicking and dragging them into place.)

Now I just need to refine the drawing, weighting the lines to simulate the drag of a brush and emphasize important features. I’ve also corrected the proportions of his face, which were too tall and narrow before. The line drawing is done, so now I’ll drop it into the cover layout.

The finished cover features flat colors and modern typography, inspired partly by classic Blue Note jazz album covers. A colored background provides structure to the layout and an additional pop of color to make the book stand out on bookstore shelves. Finally, the cover is printed on uncoated stock, which gives the book a slightly worn-in feeling, hopefully imparting to the reader a subtle sense of the long history behind the author’s work.

Next in the series is Jacques Derrida. The distinctive features I noted in my rough sketch include a strong, broad face, high cheekbones, and a shifty look in his eyes.

The tight drawing clarifies these features even if the proportions still aren’t right. Derrida cut a dashing figure, but I felt his portrait should impart his sly sense of humor as well.

Here I’ve scanned the tight drawing and recreated all the linework digitally as before, but something still isn’t quite right…

Giving his head a slight tilt and highlighting the shifty look in his eyes finally captured the subtle humor of his expression.

Although Derrida maintained his youthful good looks into his old age, for the final cover I added some more wrinkles and lines to his face, so it’s a little clearer the book is a conversation from the end of his life. And a bright red background and typography capture his engaging presence.

Last in the series (for now) is Kurt Vonnegut. In my rough sketch, I identified his small face, wild hair, and wise smile. And the moustache, of course.

I refined the features (and dialed down the expression) in my tight pencil drawing. At this point it occurred to me that Vonnegut resembled Mark Twain—a coincidence I feel he may have cultivated.

My first stab at the linework is close…

But I’d made his face a little too tall. The proportions feel a little better here.

Finally, a slightly bluish green captures Vonnegut’s vitality and wit, which, as the book makes clear, was with him right to the very end.