The game that sticks the most with me is the Veritable Conglomeration of Badasses. Technically this was just one game. One of the early games Wirty, Chad, and I had involved my first D&D character, Will, meeting Wirty's prismatic dragon (created using Council of Wyrms). Both had flying ships and worked together. We had other characters that we played, but it always came back to those characters and their ships. New characters would be created and they would end up joining up with the crew. There were humans, dwarves, drow, saurials, and even Storath's adopted son, my thri-kreen Karn. At some point, we started referring to the group as the Veritable Conglomeration of Badasses. Eventually Storath ascended to godhood and we went into the next generation. My favorite character from that time was Ulic Razorwing, Will's son. Ulic is one of my all-time favorite D&D characters and was the inspiration for the Wandering Nephil. Below is some Ulic artwork. The first two pieces were done by my little brother, Devan. The last was done by one of my dearest friends, Amber.
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