Villains becoming sympathetic - done well, done poorly, general discussion

He flip-flops too frequently to qualify, even if he is easily the most charismatic when he’s allied with the heroes in the RPGs, he still tried to rewrite the universe and kill Mario as an infant via time travel afterwards.

Donkey Kong and Wario are better examples (though, the former may not be the original).

Then there’s King Dedede and Meta Knight from Kirby.

I’m really not going to bother listing video game characters; this trope is very prevalent in Japanese media. Can’t really think of any Western examples, though.

This has also happened to Pete in Disney - went from being the villain in the original shorts, to Goofy’s rival & neighbour, to one of the peripheral cast in Mickey Mouse Clubhouse today - he’s portrayed as a bit of a pain but still gets to go to the parties.

I always wished the whole show - Xena: Warrior Princess - had been less camp. Although even if it had I suspect it would not have worked…

Anyhow. The character of Xena was introduced in Hercules: The Legendary Journeys as a pretty good villain of the week. Then had a dignified and reasonably justified conversion to troubled heroine and her own spin off show.

TCMF-2L

Ooh! Best Disney expample: Experiment 626 aka “Stitch”! Rotten little monster tamed by equally troubled little girl.

I don’t know though; not that I disagree with what you say about Hank vs. Walt, but rather that Hank never had a Heel/Face turn. He didn’t really change in terms of being a good person with a clear moral center; it was revealed through the series. Similarly, Walt wasn’t ever good, which was revealed.

By comparison, G’Kar on Babylon 5 did clearly change over the course of the series. He was a venal, obnoxious minor asshole at the beginning, almost became a real villain, and then underwent a sort of metamorphosis that caused him to be a holy Narn of sorts.

I kind of think (and correct me if I’m wrong) that the OP is looking for more examples of the G’Kar sort, not the second sort.

And I don’t think I’d include the “disaffected minor bad guys (who aren’t really bad) who finally have an option not to serve the big bad guys” trope either, a-la Teal’c and Bra’tac of Stargate SG-1.
Expanse spoilers ahoy!

So far, in the Expanse books, Clarissa Mao is a pretty good example of a well done villain to sympathetic. Originally she was entirely villainous and kind of unsympathetic in “Abbadon’s Gate”, but by explaining her motivations and the effects of her choices, they were able to write her into being much more sympathetic by the end of “Nemesis Games” and through “Babylon’s Ashes”. They do a surprisingly good job showing that this heel/face turn hasn’t exactly gone over terribly well with everyone in the crew, particularly Holden.

Ohh, good one.

Okay, okay, we are going with video game characters, we are going with other cartoon characters, I’m going to have to say it. Starlight Glimmer. (And somewhere out there, Calico Jack is feeling a disturbance in the force.)

Harmony? You have to be kidding. She went from being an obnoxious and manipulative human to being an obnoxious and manipulative vampire, and a traitor to boot.

Now Anya I’ll give you.

G’Kar’s transition is a pretty good one because there’s a strong character reason for it. At a moment when he was about to do something truly awful, he had a Road to Damascus conversion due to a vision of G’Quan, which set him on another, better path (okay, it was really Kosh he saw, but G’Kar doesn’t know that).

Another reason Jaime Lannister works well is because the reader/watcher gets to see things from his point of view, and learn that a lot of stuff that he gets flak for is misunderstood. Everyone hates him for being the “Kingslayer” for example, but that was actually a heroic action (killing Aerys before he could blow up the city).

One very interesting villain-turned-good guy recently: Megatron in the IDW Transformers comics, renouncing Decepticonism and becoming an Autobot. There are parts of it that have been very well done - Megatron himself struggles with his change in character, Decepticons are split between feeling he’s a traitor or feeling like it’s part of some secret master plan, and Autobots are split in how far they trust him. Some of the Autobots become a bit too accepting/buddy-buddy with him (which actually does feel a bit forced by the writer), and it leads to a mutiny by other Autobots.

Continuing with Transformers, I’d say in Beast Wars that Dinobot was a well-done example, whereas Blackarachnia was a poorly done example (as the switch basically ended up taking her personality along with it).

This is out of date, actually. There’s a Venom, now, a villain again. And Eddie’s been bonded with Toxin for a while.

Put me in for another vote for that c*cksucker Al Swearingen. I found him far and away the most interesting, textured character in the series and, as the OP stated, he emerged as the heart and soul of Deadwood.

Eh… much as I love Buffy, and as entertaining a character as Spike was, I think the transition was a bit clumsy. If nothing else, the fact that it depended on a techno-magical chip meant that it never really felt like actual character development.

He also suffered from another cliche early in his time on the show, namely, “oh come ON how does he keep getting away”. When two mortal enemies supposedly as powerful and effective as Buffy and Spike are repeatedly trying to kill each other dead, and both of them always manage to survive, it kind of diminishes the threat level going forward.

This is a great answer, and certainly fits at least the spirit of the thread if not the letter. Hank starts out as a boorish annoyance and ends up being a truly virtuous character.

I see what you’re saying… although I think that a character who switches over the course of a single self-contained work is very different than one who switches over multiple TV seasons or multiple films. It’s obviously not the case that Dr Seuss originally intended for The Grinch to be a traditional villain, and then only changed his mind after seeing the fan response, or anything along those lines.

I wonder who was the earliest fictional such reformed character?

You could probably stretch both Gilgamesh and Enkidu to fit the category.

I’d nominate Lestat for the worst conversion from villain to hero. He’s an amoral killer all throughout Interview with the Vampire and then in the next book and for the rest of the series it turns out that he’s just misunderstood, man. Then he becomes Anne Rice’s fictional boyfriend and things get weird.

I think that should go for all vampires of the “sure, I killed countless thousands of people over the centuries of my life, but I don’t do that anymore so I’m okay now” category.

Enkidu did cross my mind but Enkidu isn’t bad; he’s an opponent. And he’s encountered and becomes Gilgamesh’s friend early on.