Boris Vallejo is one of my favourite "joke people", largely because of Hyborian Gates:
But also because really, even when not making magnificent catastrophes in game form, the dude could not resist doing art like that anyway. Severely 80's-coiffed women riding chrome animals was actually a very common theme of his clearly a fetish of his.
I was at a card and comic book show when I was a teenager and Hyborean Gates boxes were on sale for 4 dollars a booster box. Also, Wyvern the Collectable Card Game.
I am sad to say the only two games I have ever had a complete set of were Hyborean Gates and Wyvern.
Words really cannot express how fucking
bad Hyborean Gates was. Not just the art, but the gameplay mechanics. The booster packs would come with little cards that had cut-out things you'd assemble into little papercraft markers to put on cards. The rules were completely incomprehensible. I spent hours reading that little manual that came iwth the starter decks and was NEVER able to figure it out.
Wyvern on the other hand was honestly pretty good, but nobody played it and the art was miserable.