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 (passed away June 28, 2020). 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; Battletech, Paranoia, and Tales from the Floating Vagabond, plus covers for Dragon Magazine and Dungeon. The guy was prolific and adapted to genres ranging from comedy to horror, fantasy to sci-fi, ninjas to westerns with spies and gangsters in between.
Holloway tends to be forgotten or dismissed in the shadows of the Four Greats. Maybe because he did a lot of humor. Maybe because he started with interiors, just black and white, and then moved to painting primarily after leaving the Pit. It took me a little longer to appreciate him as much as Elmore and Parkinson, but he should be appreciated.
You get an excellent sense referencing historical armor and weaponry in the two black and white interiors below. I'm not sure where Holloway's piece comes from, but Sutherlands is from the original D&D Holmes Basic boxed set, happily stamped onto into brain from age 5 or 6. I have to wonder if Sutherland was an early influence on Holloway's TSR artwork.
Sutherland (pig faced orcs!, from Holmes' Basic Dungeons and Dragons, 1977)
The first thing stands out in Holloway's style, sets him apart from the Four Greats, is his use of 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. It's also present in Sutherand's art. I've mentioned Holloway's kinetic energy already in figures and scenes, and his use of true historical references. There's something else that sets obviously him apart from the Four Greats - his women look real. They are not models or bombshells. That must be another reason he gets shoved to the back. His women have a certain look. Nerds. The girl at the game table. The goofy classmate. It's refreshing, but not exactly what draws in pre-teen and teenage boys. Finally, Holloway at least has the feel of someone who played RPGs. Many of his scenes show a playfulness that reflects the interactions of the players running the characters in the games.
(Interior from Kim Mohan's 1986 Wilderness Survival Guide; all of Holloway's style elements in one.)Below is one of Holloway's earlier Dragon Magazine cover paintings with a typical female figure. Again you get an immediate feel for grounded realism despite the goblinoid s below the tree. On a side note, it is very difficult to find online libraries of Holloway's paintings. There are almost always seen as cover art. He didn't have his own website or online store. This again sets him apart from the Four Greats.
I first encountered Jim Holloway's work at age six, when my cousin Eric passed us the over-used copy of his Holmes Basic D&D set missing many pages, along with a battered but still complete D&D adventure, Tom Moldvay's The Lost City, a true classic of RPG writing. The Lost City may have been Holloway's first color painting cover for TSR. We tried running the adventure several times but never got very far as youngsters. I'd like to give it another go as an adult. The art work, however, was completely adsorbing for me. Again, Holloway seems to have studied his subject, maybe from several Osprey military books illustrating period uniforms and equipment. Everything fits. You can almost place it as 11th to 12th century Mediterranean with a bedouin Arab mixed into the group. Holloway takes that historical approach and turns it on its head, shocks, with the addition of the fantastical. It's also a joy to see the same character's used throughout. I love, love, love it! Here are some highlights:
(Holloway's cover for Tom Moldvay's The Lost City, published in 1982)A few more items of note on Holloway's composition to which I will attach some of his art: his ability to do battle scenes, and his connection to Japan and the orient. I'll tackle battle scenes first. He did a cover for an RPGA adventure while at the Pit which hinted at his ability to tackle complex scenes packed with characters and action. He followed that up as a freelance artist some mouth watering illustrations plus one evocative cover for Dragon Magazine.
(Holloway's cover for Jordan Wiseman's 1986 Tales of the Black Widow Company for FAFSA's Battletech RPG. It's pretty much a stand out classic in the genre and shows a little of what Holloway was able to do when he got out of the Pit.)


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