Of all the artists who made their debut during the Golden Age of D&D -- his first TSR work was in 1981 -- I think it's Jim Holloway who catches the most undeserved flak. Perhaps it's because he's so closely associated with West End's Paranoia, the darkly humorous science fiction RPG, for which he provided the illustrations. As much as the text itself, Holloway's artwork defined what that game was about and, for many gamers of a certain vintage, it also defined Holloway himself as a "jokey" artist -- highly inappropriate for old school D&D.
I myself think that impression is mistaken. There's no doubt that, especially after he'd done his Paranoia illustrations, Holloway's art tended to include more humorous elements than they had before, but those elements were always present; it's just that Paranoia afforded him the opportunity to cut loose in a way he hadn't before. Of course, that's no defense of the man in the eyes of many, whose conception of D&D leaves no room for humor, even the gallows humor Holloway frequently incorporated into his artwork.
I've always found such criticisms to be odd, since old school D&D, with its fragile PCs and mechanical randomness, is in my experience of playing it filled with moments of black humor, not to mention outright slapstick. Far from being contrary to the old school spirit, I find Holloway's illustrations to look like "photographs" from many an adventure I've run, with the party tripping over themselves in flight from a deadly monster or finding themselves in a sticky situation that'd be funny if it didn't spell their likely doom.
And while his style is very different, Holloway comes closest in my opinion to capturing the grubbiness of the adventuring life that Dave Trampier illustrated so well. Holloway's people aren't nakedly beautiful and heroic like those of Elmore or the other "fantastic realist" artists of the Silver Age. More often than not, they're lumpy-faced, gap-toothed ruffians with five o'clock shadow and distinctly unheroic demeanors. They're not runway models at the Ren Faire, that's for sure, but that's frankly the appeal of Holloway's art. He nicely evokes the dingy, hardscrabble existence an old school D&D character lives if he has a referee who clings to the Old Ways without apology.
Far from being contrary to the old school spirit, much of Holloway's art is a superb exemplar of it, as his recent contribution to Knockspell shows quite well, I think. I hope he'll get the chance to do more old school products in the coming weeks and months. Holloway's work provides a nice counterpoint, both esthetically and thematically, to over the top style so in favor in much of contemporary fantasy gaming, making it one of several artistic guideposts for what old school gaming is about. Goodness knows we could use some more of that.