Here's what I think was one of my better pieces from my early days there, art from the first of a two-page feature called "TV Gameshows Through History", written by Rob Weske, and published in the pages of CRACKED back in 1992. All the art and lettering are mine, done with Higgins waterproof black ink in dip pen and brush, plus some fine-point Rapidograph pen.
Like the "mutant artist" banner art at the top of this blog (itself originally done for CRACKED), this was done on Duo Shade board, which was a special, chemically-treated paper that had 'invisible' diagonal hatching and crosshatching lines printed on it, that could be brought out by using two separate chemical solutions with a brush or pen. So, basically, you could draw or paint in a couple of values of grey tone in a black and white illustration, which would show up nicely in reproduction/printing. With the advent of Photoshop tools and high-res computer printers, Duo Shade eventually became both prohibitively expensive and, ultimately, obsolete... but it was an interesting medium to use, at the time.
Here are some detail shots--
I liked to put in old pop culture reference gags, wherever they might fit... so in the arena above, around Kirk Douglas, you can find forgotten 1950s Terrytoons character, "Flebus"; Super Chicken's crime-fighting partner, "Fred"; the lion logo from Random House's old "Step-Up Books" line and, hidden somewhere, the Little Caesar's "Pizza! Pizza!" guy.