I have a "Workshop" feature in the current issue (in the U.S.) of Imagine FX #80 titled "How to Draw and Paint a Poster with Type." Over 4 pages, I outline how the above illustration was created in a number of annotated process-based steps. I cover my thoughts on draftsmanship, type design, reference photography, value, etc. Also, in the back of the issue you can find a CD containing all my working .psd files from this project that you can download and explore!
Thanks to Claire, and all the fine folks at ImagineFX!