I am sure I had some memorable characters from my middleschool/high school days, but most of those are a haze to me. I think the first memorable character I made, the one that makes you give a chefs kiss and want to use them again somewhere else, is my frequent dnd character I play: Durge Blackboot. Originally, I called him Dirk (I was on a biiiiiig Homestuck rage during my senior year of high school) I picked durge just because I thought Dirge sounded cooler but just happened to spell it wrong. Backstory is always the same: A half-orc raised by the blackboot tribe, Orcs from a sort of wetland/swamp, usually in the north. They get greedy and attack a nearby road until people retaliate and nearly wipe them out. Durge is out trying to make money for his family. They've relocated and are licking their wounds. It's a fairly standard character, all things considered, but it's delightfully fun to play. I always felt his orc family could be some moral complexity to the character, too. His people are raiders. Is it right for him to help them? I originally played him as a weird multiclass build, trying to fish for big crits. It was baaaaad, and so was that game. I later played him as Durge v1, now as a battlemaster fighter, which is ironic because this version of him kept getting his but kicked by a wandering duelist. Last time I played him he was a paladin, which, while I enjoy paladins, he simply did not act like one. He was always missing teeth, had a screwed-up nose from breaking it so often, covered in scars. Big burly guy, but just on the taller end of humans, closer to 6'5 ot so. He always had long, shaggy hair that really needed to be cleaned/combed. He was a pretty rugged guy, but kind overall, if a bit simple. As a guy who writes all the time, I kept using big words, which had people in character asking 'where did you learn that?' or 'wow, wasn't expecting that' so I started making him smarter than he acts. Not that he's some genius but he purposefully plays a little dumb to seem less dangerous to the people he would probably eat if he got hungry enough. Overall, I liked playing him because he was a tough enough guy to see him fail. More often than not, his sheer endurance was what made him stand out. A Dirk, he beat Domn, a paladin with some lucky crits, and he always just completely floundered in his rivalry with that duelist, and as a paladin, he all but single-handedly took on a veritable army of goblins while the other players didn't engage.