My friend Bob Staake posted a video that shows how he illustrated the cover of the latest New Yorker. He still uses Photoshop 3.0 and Macintosh OS 7!
I suppose I have a pretty unusual way of working -- at least that's what my illustrator friends are always telling me. I start by creating the most basic shapes and then refine with details as I go. To me the process feels completely normal. I look at that stark white space in front of me and can see the entire fully completed image in my head. Maybe I'm just lucky that way.The making of Bob Staake's New Yorker cover