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.
What do I love about Holloway's D&D art? His work is often 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 Sutherland's use of historical armor and weapons rooting old school RPGs to history, and thus real, gritty. It makes for good fantasy RPGs in my opinion.
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.
Holloway (generic goblinoids, but always more interesting than those of the 4 Gs) 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.
(Holloway girl, Dragon Magazine #88 published Aug 1984)
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)(Principle interior art piece laying out the the opening of the adventure. Brilliant!)
(There's the fantastic intruding on realism)
(Who knows why, but this one gave me nightmares and I stopped playing D&D for several years)
(Holloway's humor on display.)
(Perhaps Holloway's most famous creation, Zargon, at the bottom of the Lost City.)
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.
(Cover illustration to Frank Metzer's To the Aid of Falx, published for the RGPA in 1982.)
(Unknown source and title. Holoway did a series of dwarven battle scenes like this one.)
(Unknown source and title. There is a lot of action and tension packed in here.)
(Unknown title, but this cover to Nov 1987 Dragon Magazine #127 deserves to be seen in its own right.) Moving to to Japanese samurai and ninja themes, I've read that Holloway was part Japanese. One half, one quarter, I do not know. Regardless Holloway did a series of cover paintings for AD&D's Oriental Adventures and Eastern Realms source books and adventures. He was TSR's go to artist for these settings. He also di several Dragon magazine covers with Japanese themes. Here are two of my favorites from the genre.
(David "Zeb" Cook's 1987 Blood of the Yakuza. Ninjas and such were huge in 1980s America)
(Jeff Grub's 1988 MM vs. the DC. This one-on-one duel was perhaps unique in TSR cover art.)
Here I'll return to Holloway's kinetic dynamism, which sets him apart for the Four Greats. You see it above with Mad Monkey, and below with one of my favorite Dragon Magazine cover paintings.
(Holloway's cover to Sep 1990 Dragon magazine #161)
There is much, much more to Holloway's artistic repertoire, but this post mostly represents his working under the the shadow of the Four Greats. I wonder if that was a motivator for him leaving the Pit? I'll add these three paintings to close. The bulk of Holloway's work post TSR material I will save for another time.
(David James Ritchie's 1982 adventure Ballots and Bullets. I think Holloway depicted Pit artists in the faces. Easley is certainly present in the front right, Elmore likely on horse in rear left.)
(Holloway's cover painting to Feb 1992 Dragon magazine #178. Nobody at TSR could do dwarves as well as Holloway., which remain a staple of Tolkien inspired fantasy.)(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.)