Bill Willingham
Ahem... that's "Eisner Award Winner Bill Willingham" to you. Bill's work epitomized "the Moldvay era" to me, from the dungeon party fighting the dragon in the '81 red book, to the picture of the phanatons attacking that dude on the title page of X1. These days, Bill's as much of a writer as an artist, but if you grognards are feeling nostalgic, Jeff over at Jeff's Gameblog has put together a nice mini-gallery of Bill's D&D stuff.
Jim Rosloff
Roslof's owlbear from the title page from B2 will always be THE picture of an owlbear for me. (And from what I've seen around the interweb, I'm not the only one who thinks that.) And, damn, how cool is that picture of Thor playing whack-a-mole with the Midgard Serpent from Deities & Demigods? James at Grognardia did a nice series of posts about Jim earlier this year after his passing (R.I.P, Jim.)
Rodger MacGowan
I can hear it now... the collective, "WHO?!" out there in the blogosphere. And rightly so, as MacGowan is an oddity on this list (and the previous list) for a couple of reasons: 1) while he did illustrate many of the games he worked on, MacGowan is better know as an Art Director/Designer, and 2) art director types don't usually get too much credit, even when they're as prolific as MacGowan--his art and design graced the covers and interiors of an unmatched list of wargames that number around 300 and include the likes of Avalon Hill's Squad Leader and PanzerKrieg, as well as Yaquinto's Swashbuckler. To me, MacGowan's style, particularly his use of high contrast photo-imagery as well as illustrations that mimic that look, defines wargame graphics of the late 1970s/early 1980s. Moreover, as the art director/designer of the work (a luxury most freelance illustrators don't have), he really created a "look" more so than just creating "art" for the games he worked on. MacGowan is now the editor-in-chief of C3i magazine, where you can find a more complete profile of RBM himself.
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