“Jim brought a playfulness to TSR’s in-house stable of artists. His fine linework and natural humanoid poses were informed by an inner chuckle. You could tell this was a man who saw humor with every glance. As an artist, he brought that humor to the surface. Every battle, every monster, every spell: just beneath the surface—and occasionally right on top of it—there was a joke waiting to happen.”Here is his famous cover illustration for B4, The Lost City (now rereleased as part of Goodman Games’ “Original Adventures Reincarnated” series):
Deep within the Lost City dwells the Lovecraftian horror "Zargon":
Holloway’s work for D&D, AD&D, and Paranoia are well-known. The interior art of Gary Gygax’s Monster Manual 2 was entirely by Holloway. He also did some work for ICE’s Middle-earth line. Below are some pictures from the Pirates of Pelargir module.