The fifth entry for chess art is probably the most deserving to win an award, although it's unlikely for a number of reasons.
After writing that I discovered the artist's Wikipedia page, Jovan Prokopljevic, which says,
He was awarded the first prize, 'Best Cartoon' category, by the Chess Journalists of America in 2004.
This is confirmed on an archived CJA page, CJA 2004 Journalism Awards (chessjournalism.org; '"Try a Transfusion of Empire Chess" by Jovan Prokopljevic. Empire Chess, Summer 2003'). In my own archive I found an excellent example of Prokopljevic's work, shown below.
The image description, from a 2001 eBay auction, said,
Collection of 13 caricatures of FIDE champions (from Steinitz to Kasparov) published by Chess Informant; illustrated by J. Prokopljevic 1996. All prints on approx. 8.5" x 11" pages in color. Each caricature has name of champ and dates of title reigns. Comes in collection folder with all caricatures on front. Folder autographed by artist on inside pocket.
Several collections of Prokopljevic's cartoons have been published, but I wasn't able to catalog them in the time available for this post. I'll save that for another time, as in Chess Champion Trading Cards (July 2016).
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