"Artist Bob Stake used Photoshop 3.0 on Mac OS 7 to create this cover for The New Yorker recently. I guess you use what you know… The video above shows Bob progressing through the design, it’s a nice glimpse into another artist’s process. The whole story and more details are here. Via Gizmodo" -iso50
i tried my hand at bob's style. took about 20 minutes to come up with my version. not spot on, but this was my first time. the video helped a bit to understand his technique. i watched the twice before hand and then had at my attempt without further help from the video. i only referenced the final product to try and understand the shapes he used.
definitely something worth dabbling in. give it a shot.
plenty more videos of bob at work. that guy is a mad man.
[video 1] [video2] [video3]