Harkan Kirthak on A Moment in Tyme. He started out as your typical high school "my character died, let me introduce his brother," character and ended up with such a rich and tragic history. Sure, a lot of that history was insane, but in my defense, I was pretty young at the time. So he started out as an Andoran-noble-born Child of the Light (sorry, Whitecloak). A junior officer. He connected with another Child of the Light, an Inquisitor, only for her to be killed by an Arch Inquisitor. Thus started Harkan's feud with the Inquisitors. He also intercepted a courier delivering a heron-mark sword to a new Blademaster, and when the man used the sword to defend himself, took it for himself, believing that he had defeated a Blademaster. He eventually gained proof that the Arch Inquisitor had killed the Inquisitor over false accusations (I don't even remember how), and so when he killed the Arch Inquisitor, he had political cover, although he was forced to leave the Children of the Light. He fought along the Blightborder for a while, married a Cairhienin, helped her fail to take the Cairhienin throne (she died in the attempt), went back to the Blightborder, and then joined the Queen's Guard at 36 (after I had played him for... 10ish years at this point?). He eventually became a Captain, then was forced into retirement when Gaebril took power in Caemlyn, and came out of retirement to become Captain-General for Elayne. I eventually killed him off at age 50, having played him for 15 RL years and 31 IC years across four timeline reboots. He gathered a fascinating crew of NPC guards over the years, and in all that time, never once told an outright lie. He just wouldn't do it.
Volkare Previn was a Zabrak Sith Trooper on Knights of the Old Republic. He fought as a teenage guerrilla when the Mandalorians invaded Iridonia, and then enlisted in the Revanchist's forces immediately upon the planet being liberated. His fall to the Dark Side was a slow one, as reasonable, violent actions piled up, and more violent actions became more reasonable. His fall was spurred on by his beginning a relationship with a Sith Acolyte (he originally slept with her because a) she offered, and b) he thought it would help his career, but they eventually became a very effective partnership), and being around her and her madclaw Wookiee Sith Master. Said Wookiee ripped off one of Volkare's arms to show how little he thought of the relationship (he got a cybernetic replacement), but eventually the devious violence of Volkare's plans impressed the Wookiee, who became a (grudging) second patron. Volkare became an officer, murdered his boss's boss in cold blood to secure his boss's advancement and his own (and to have something to hold over his boss if necessary), learned to use a lightsaber (not particularly well), and generally made life good for his subordinates and hard for the Old Republic. The fact that the Sith Acolyte's player became my wife years later, of course, has absolutely nothing to do with how fondly I remembered playing Volkare.