Part of the issue is that if you start at level 1, that sort of limits how much villainy you can get up to before you got that level. Plenty of my characters were criminals, but pre-level 1 crime is sort of at the subsistence level.
Probably the most "hard turn away from villainy" character I had was a waker may changeling (used to incubate the souls of night hags while they metamorphose into more powerful dreamthief hags) who escaped the coven responsible for corrupting her, figured there was something fundamentally wrong with her, then went and read enough books to learn what's going on, and subsequently became a Paladin. But since her soul is fundamentally evil, all of her instincts regarding right and wrong were backwards, so she had to mediate "first impressions on what to do" with book learning regarding moral philosophy. It's a fun RP challenge to play a character who must not do evil, but whose first impulse is always to do things that are petty, selfish, and cruel.
I had an idea for a redeemed villain character when I was still playing 3.0. I didn't get to play him until I'd been playing pathfinder for awhile. Pathfinder mechanics mean that it wouldn't quite work the same way but my DM let me keep the backstory since he liked the concept.
Anyway, the original idea for the character was that he was a Rogue/Executioner/Anti-paladin. He had a horrible encounter with something that level drained him back to level 1 before he escaped. The experience was so horrible that he sought atonement, destroyed/donated most of his gear except for his now non-magical sword. Which he kept as a reminder of what he once was. He would then start leveling as a paladin. I think I had some way to re-qualify as executioner again but I don't really remember the details now. I also had the idea that his sword would slowly regain it's powers in an attempt to tempt him into using it and falling back into his old ways.
The pathfinder version of this character was a Rogue 1/Paladin(X). His patron deity was Korada. So, I took the feat improved unarmed strike and the trait heirloom weapon - Rhoka.
When fights broke out he would try to deal with things just using unarmed strikes, but he had the option to pull his old sword (the Rhoka), when things got bad. He had a high enough str that at low levels he was able to get away with it. But more and more fights he was having to pull the sword. It also meant that he approached even obviously evil enemies at least initially as being possibly redeemable. After all, he himself was pretty terrible and was able to be redeemed.
At one point We encountered a demon in the middle of a wrecked village. My character really wanted to attack the demon, but was forced to ask questions first. It turned out the demon wasn't responsible and never said anything that gave my character an excuse to attack him. In the end I had to let him teleport away since he wasn't "doing anything wrong" at the moment.
The game was supposed to be more roleplay centric then what our DM typically ran and was started in response to a player that had joined the group and essentially complained that things weren't "realistic" enough. He quit the group and so the DM went back to his normal sandbox game. Meaning I only got to play the character for a handful of sessions.
He was fun and was played very sub-optimally for roleplaying reasons.
I can only think of one character who had been a straight up bad guy in the past. He was a priest of an evil god of the ocean and storms and he used his powers to help pirates wreck ships, and to subdue port towns and such. The captain messed up and picked a target that was too big and the crew had to quit and go into hiding. The storm priest went high into the mountains living as a hermit and acted as a respectable healer for a small mining village. The priest's powers were stripped from him for having forsaken the sea and denying his god a life, but some unknown diety continued to grant him healing powers. After years of pretending to be a decent person, he couldn't remember who he had been before and just kept up the act.
My last paladin was technically an ex-mobster (Sczarni), but he never really took to the family business anyway. His brother the oracle, on the other hand, . . . Shame I never got to play him. Dude was not very good at the whole "not conning people" thing even when his fortune-telling accidentally started to work.
Part of the issue is that if you start at level 1, that sort of limits how much villainy you can get up to before you got that level. Plenty of my characters were criminals, but pre-level 1 crime is sort of at the subsistence level.
Obvious answer to this is to not start at level 1. I feel that games where the PC's have some level of pre-existing accomplishment and ability make for more interesting narratives, though this is about as YMMV as it gets.
That being said... I don't think I've ever actually played a reformed villain. I've played a few characters who grew up in a situation that made them a criminal, though those have been "good person doing what she must to survive" types. Might be something to consider for my next character!
Have you ever played a character who used to be a bad guy, Like a bandit or something, But through one way or another found redemption and became a good guy?
Sheesh, I thought everybody did this!
If so, What did your redeemed bad guy do before he found redemption? How did he find his redemption? And what did he become after?
I've had former assassins, religious fanatics, a reformed graverobber.
Past crimes have ranged from the petty to the obscene, and reformation has ranged from the, "eh, I'll keep doing the same things because they're all I know how to do, but now I try to do it to people like I used to be" to "goodbye to all of that, I'm a pacifist monk now."
I most certainly have, but probably in a more unique way than some others. See, I was playing Hell's Vengeance (an adventure path for EVIL characters) with a Life Mystery male Tiefling Oracle that worshiped Asmodeus, dabbled in playing a courtesan for the nobles, paid lip service to Callistra, and enjoyed bringing pain for a purpose (torture). He was the "I hate to waste a tool" kind of evil and was quite reluctant to simply kill people in order to accomplish his goals, though he wouldn't shed a tear if it came to it. So, Neutral Evil (Legalistic Curse).
How did he become Good? Divine intervention, actually. One of their minions managed to get inside his head and make him start doubting his chosen course. He was created with particular character flaws that allowed for such manipulations to take place and it was always my intent that the forces of Good could win him over, in the end.
His redemption was a rocky path of learning that the pain of others was not a toy, and even if he enjoyed pain (as a source of pleasure), others were very unlikely to feel the same way about it. His idea that people were tools morphed into viewing them as real people as unique as himself and that was why they had value, not just because of what they could do for him.
He eventually became an NPC under the control of the DM because I could not very well play a character that would eventually turn on the party and actively stand against their agenda. Well, I COULD have done it, but I firmly believe that the DM needs to the architect of that kind of opposition to the players.
For certain values of "reformed." My first Pathfinder character (about a decade ago, using the PF1 playtest rules) was a CE tiefling rogue. I joined while they were most of the way through Savage Tide, so the GM handed me an NPC that was convinced to change sides previously by an absurdly high diplomacy check. He was a pirate, demon cultist who was stuck on an island to oversee part of the evil plan. I also decided he was a cannibal, and a lecher. Mostly I played him for camp value. Although I never did garnish the mermaid ranger like I planned (the plan was she'd wake up with parsley behind her ears and lemon wedges around her). He did turn a monster's head into a hand-puppet.
Also had a fun moment where we were rescuing our patron from a prison in the Abyss. While the rest of the party was dealing with her, he wandered over to a cage hanging over a lava pit with an ice devil in it. The devil tried to get him to release it. He asked if it would pay him. It answered poorly by saying "no". So he responded "Ok, then eat lava." and pulled a pin and dropped the cage. There was a discussion after the fact of whether that was an evil act or not. "It was a devil he killed. Killing those isn't evil." "Yeah, but he tried to shake it down for money first. That's pretty evil."
Much of the party was very hostile to him, and tried to restrict him with magic or even chain him up, except ironically the group's Paladin. The paladin stated simply that he was free to do what he wanted, but if he acted evilly, they'd just kill him and be done with it. My character appreciated that. Both the understanding of the importance of freedom, but also the honest harshness if you abused that freedom. The paladin became the closest thing to a friend he had. Eventually he went CN, ditched demon worship and decided that privateering was even better than piracy. You just attack bad people, then it's ok to take their stuff! Still an unpleasant and disgusting guy who enjoys making others uncomfortable, just not actively evil (he still occasionally sneaks a snack of someone already dead. Waste not, want not.)
Normally I tend towards more heroic characters. So not a lot of bad actions in their backgrounds. I did once do a grave robber, but he wasn't really bad, just neutral and taking advantage of access to graveyards (he was a headstone carver) to get extra money to fund his research. Even my recent thief character was more of a Robin Hood style thief. Maybe I should put some darker stuff into some upcoming characters backgrounds to change things up a bit.