Though Denis Loubet is widely recognized for creating the art the graced the cover and manual for Ultima Underworld, the actual concept for the box art came from Warren Spector, who submitted numerous ideas and sketches to Paul Neurath (the game’s designer) and Richard Garriott for approval. Here are a few of those submissions:
There are also a couple of scanned facsimilie cover sheets, addressed from Warren Spector to Paul Neurath, asking for comment and approval on the sketches. Some of the sketches also have penciled-in comments, probably from Paul Neurath, asking questions about (or suggesting changes to) different designs. For example, on one sketch — depicting the Slasher of Veils and the wizard Tyball looming over a cowering (and sexily-posed/scantily-clad) Arial, Neurath comments that: “the girl’s pose should probably change (maybe more clothes…)”.
And of course, something very similar to the final cover design appears in the set as well. Although at some point, Spector’s initial sketch (depicitng the Avatar holding a torch at the top of a stairwell) changed a bit (with the Avatar’s pose becoming more combat-ready, and with the torch being replaced by a shield).
Image Credits: Joe Garrity/Origin Museum, and Steve Emond for forwarding.