I recently came across the original CD-ROM in which artist Hugh Jamieson delivered the original Shady O'Grady's™ Rising Star cover art. It's dated 9/22/05, which means as of two days ago it's been 20 years since he created this cover art. However, the game itself wasn't released for another year and a half.
Nowadays many people would probably look at this and say it's AI art (I get a lot of that lately - check out the Shrouded Aspect discussions), but this clearly pre-dates AI-generated images. It was done digitally, though I can't confirm what program he used.
I've never actually met Hugh in person. I found him on deviantart.com and sent him a message. He was nice enough to cut me a good deal on this custom work, because he liked the project.
Apparently, Hugh is still at it, creating cool art. Check out Hugh's web site https://hughjamiesonart.com/
