Friday, May 8, 2026

Art of the Fifth Wheel - Jim Holloway!!!

 I'm returning to D&D art, returning to TSR's Pit. The Pit had the Four Greats of fantasy genre oil painting - Elmore, Easley, Parkinson, and Caldwell. Then there was Jim Holloway. He worked at TSR's pit from 1981 to 1983, had a freelance career before and after. For the after, Holloway continued to do commissions for TSR, including Dungeons and Dragons. Somewhere I read Jim Holloway was self trained, self taught. Somewhere I read he was the workhorse of the Pit. He did produce a very large catalog of black and white inks that filled the interiors of many D&D books. That has to be my focus, because that is where I mostly encountered his work. But let it be know that he did interiors and covers for many RPG games, most notable MechWarrior, Battletech, Paranoia, and Tales from the Floating Vagabond, plus covers for Dragon Magazine.  The guy was prolific and adapted to genres ranging from comedy to horror, fantasy to sci-fi. 

Holloway tends to be forgotten or dismissed in the shadows of the Four Greats. Maybe because he did a lot of humor. It took me a little longer to appreciate him as much as Elmore and Parkinson. What do I love about Holloway's D&D art? His work is kinetic. More importantly to me, his work connects to the real world, and to history. As an old member of the Society for Creative Anachronism, I have a great appreciation for Holloway's weapons, armor, and garb connecting to real world history and settings. It also connects to older D&D with David Sutherlands use of historical armor and weapons rooting the game to something more historical, and thus real, gritty. It makes for good fantasy RPG in my opinion. 

One thing stands out in Holloway's style, sets him apart from the Four Greats. He uses hard, black shadow in his black and whites, sometimes blocking out most of a figure as nothing but black silhouette. It may have been his secret to quickly turning out interior pieces for the Pit. True or not, it is very distinctive and often times very effective. I've mentioned his kinetic energy in figures and scenes, true historical references. There's something else that sets him apart - his women tend to look real. They are not models or bombshells. That must be another reason he gets overlooked, shoved to the back. His women have a certain look. Nerds. The girl at the game table. The down to earth classmate. It's refreshing, but not exactly what draws in pre-teen and teenage boys. 


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