I used an Apple Macintosh Power PC 32MB of RAM and an A3 serial port Wacom tablet, pretty cutting edge stuff at the time . And I painted it in Photoshop 3. You couldn't scale brushes on the fly then you just had to have lots of different size brushes:)
These were some of the first concepts for Herdy Gerdy PS2 Core Design Eidos. They got me the job at Core and set me on the game industry path I'm still on today.
Its a pity I don't have the .PSDs but eh . They're Houses in Foxtown by the way and did kind of make it into the final game. The original designs were done by Steve Maher
Fiddler's Green concept for a Pirates of the Caribbean game.