Monsters, Mazes, and the Moving Words of a Facebook Fan Group
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The idea behind this scene is simple: a spell cast gone wrong. But Jim Holloway had a special way of painting an encounter like this, adding personality to every character.
A self-portrait by Jim Holloway, imagining what he would look like as a warrior.
Jim Holloway didn’t just do art for tabletop games. This painting inspired by the movie The Thing depicts a Yokai (Japanese demon) shedding its skin and revealing its true form.
My father once told me that everything he loves eventually goes away.
I think he meant it in a half-joking way—you know, the way that people talk about their favorite Taco Bell menu items departing after a brief return to the fast-food spotlight. But I could tell that there was something deeper, an aura of seriousness surrounding the statement. Old friends stop coming around as often, mom-and-pop shops that you frequented as a kid go out of business and your favorite pop-culture icons grow old and pass away. That moment of vulnerability made him feel very human to me—like he wasn’t my dad, but rather a best friend I had just happened to spend my entire life with.
I felt the true weight of those words when my father passed away in 2020. His health had rapidly declined, and my brother and I were faced with the heart-wrenching decision of whether or not to release him from his pain and allow him to peacefully pass. We, as a family, agreed that he wouldn’t truly be happy kept alive by a machine. At the time, I thought about how he was right—everything I love eventually goes away, and the heaviness of that truth shattered my mental health during a year that was already tumultuous for so many other reasons.
The group remains active. Per its about section:
"A site to share and enjoy Jim's work, plain and simple. Feel free to share stories, how Jim's work has inspired you, or enhanced your gaming experiences. Please be nice or evil things will happen to you..."
Sitting in my hotel room mere hours after he had passed, I felt broken and lost. I didn’t really know who to confide in. But there was a group of strangers that I felt deserved to hear the news. I signed onto my laptop, opened Facebook, and began drafting a post in a group titled “The Art of Jim Holloway.” It was started by a fan and eventual friend of my father while he was still living, and had quickly grown to nearly 2,000 members. It’s an impressive number considering my father thought that no one even remembered his name. How very wrong he was.
Jim Holloway was the definition of an artist. Those who were close to him will tell you that his artistry was one of the few things he cared about other than his two sons. For my entire life, he never worked a “real” job. He lived and breathed his craft, staying up all night and abusing caffeine to finish projects. I believe to this day that it’s part of the reason he struggled with his health so much: the ironic tale of being so passionate about something that it kills you.
The group remains active. Per its about section:
"A site to share and enjoy Jim's work, plain and simple. Feel free to share stories, how Jim's work has inspired you, or enhanced your gaming experiences. Please be nice or evil things will happen to you..."
The creator of Dungeons & Dragons, Gary Gygax, has a memorial of his own in Lake Geneva.
In the ‘80s, he began working for a company called TSR based out of Lake Geneva, Wisconsin, the company responsible for the creation of Dungeons & Dragons. He illustrated for Dungeons & Dragons during a hectic period of the roleplaying game’s life—the media was blaming the game for the suicide deaths of two teenagers. You see, long before the alarms raised in response to other fantasy franchises, it purportedly encouraged satanism and witchcraft.
What my father brought to Dungeons & Dragons was an eye for detail and a unique sense of humor. He often paired heroic warriors with clumsy characters ripped straight out of The Three Stooges. His elaborate battle scenes took several viewings to fully take in the events that were transpiring—on a second or third glance, you might notice the intricately designed runes on the handle of a sword, or a character sneakily reaching into the pocket of another to steal his coins. It’s moments like these that define his artwork: he always went above and beyond painting the picture of what a scene called for, because he had so many hilarious and wild ideas running through his head.
The creator of Dungeons & Dragons, Gary Gygax, has a memorial of his own in Lake Geneva.
The idea behind this scene is simple: a spell cast gone wrong. But Jim Holloway had a special way of painting an encounter like this, adding personality to every character.
After I posted the news of his passing into the group, the supportive comments came flooding in. One group member told me that my father was one of the reasons he has a career, attributing the art that my father created for the BattleTech series as the reason he got into tabletop gaming. He eventually became a producer in the industry.
“I only wish I had worked up the chutzpah to tell your dad that,” the group member wrote.
There are over 100 comments like this on that post, each one espousing the unique impact that my father had on these strangers’ lives. These were people I had never met, yet we shared something irreplaceable and truly special—my father’s art and imagination shaped us into the people that we are today. I suddenly had hundreds of “family members” from all across the world mourning with me. This collective grief was still grief, but sharing the feeling made it uplifting as well as mournful.
Members of the group began sharing their favorite art pieces with stories behind them. Tales of my father’s time at TSR were passed around—one member claimed to see him churn out 100 monster illustrations in only a week’s time.
Through the group, I was able to meet up with some of his old coworkers and friends in person. We had drinks and laughed and told stories. I learned about a time when my father was questioned by the police at an absurd hour of the night because he attempted to resolve his over-caffeinated state by burning off some energy, running down the street while swinging a samurai sword.
Apparently, he had also had a disdain for upper management telling him what to do and often rebelled against the higher authority at his jobs. He fought for his creative freedom. It made sense then why he shifted over to freelance work for the rest of his life after TSR, and also why I felt inherently drawn to punk-rock music from my youth onward.
It felt like this legend was being built up around my father, each response from the group continuing to build him into this larger-than-life fantasy illustrator, not dissimilar from the heroic characters he created. It helps me remember him not how he was when I last saw him—hanging onto life in a hospital bed—but rather as I always knew him: funny, incredibly talented, and full of grandiose ideas.
A self-portrait by Jim Holloway, imagining what he would look like as a warrior.
In the end, I guess my father was wrong. I’m thankful that he lives on—not just through his art, but through the impact his creative mind had on so many people. The careers he unknowingly helped start, the timeless memories that Dungeons & Dragons players created with one another through gameplay sessions fueled by the creativity and imagination of his drawings. I only wish he knew how important he was.
I look forward to every notification I get from the “Art of Jim Holloway” online community. It means, for a brief moment, I get to feel like I’m hanging out with my dad again as group members chime in about the artwork being shared. He may not have known how important his work was to the world, but I’m thankful that I get to have that knowledge, thanks to this online community that stays connected through his art.
Jim Holloway didn’t just do art for tabletop games. This painting inspired by the movie The Thing depicts a Yokai (Japanese demon) shedding its skin and revealing its true form.
There’s a question that gets asked constantly in the group: Is there a collection of Jim’s artwork that I can purchase? The overwhelming interest has inspired me to take on the project of writing an art book, compiling all of my father’s artwork that I can get my hands on. My father always encouraged me to do whatever I wanted, and it’s a main reason why I continue to freelance write instead of settling into the predictability of an office job. It’s only appropriate that my first book would also exist thanks to him.
Everything I love will eventually go away, but Jim Holloway is forever.
