Ambiguously Evil

These are the characters whose moral standing is kept in the dark. Maybe they work for the Big Bad, but don't do anything really evil themselves. Perhaps they are Wild Cards who use the Heel Face Revolving Door constantly. Or maybe they are Evil Overlords who can seriously claim to be Reasonable Authority Figures. But one thing is certain: until they do something truly heroic or heinous, placing them somewhere in the Character Alignment is a wasted effort. Sometimes, the writers will deliberately leave it to the audience to decide what their true colors are.

Compare with Byronic Hero, Wild Card, and Noble Demon. Contrast Hidden Agenda Villain, whose motives and goals are kept in the dark but whose morality is never uncertain; also contrast with the less subtle characters who are unambiguously evil. Often a trait of the Mysterious Backer and the Enigmatic Minion.

Anime and Manga

 * In Neon Genesis Evangelion, we have Gendo Ikari, who, at the start, keeps it unclear whether he does care about his son, Shinji, and the world's safety or not. In the end, we learn
 * That's debatable - While he doubtlessly  the way he justifies his actions in episode 25 suggest that he genuinely believes that his version of the   is the only way for humanity to survive, his   make it pretty clear that he , and he still opposes the actual villains of the show with the goal of doing what he thinks is  , ultimately making him more of a
 * ...We think.
 * from Panty and Stocking With Garterbelt claims to be a demon, but could be under mind control.
 * Schneizel is, for most of the show's run, foreshadowed as an Evil Counterpart for Lelouch. But for the most part, he comes across as an Anti-Villain or even a Hero Antagonist.
 * Lelouch fits this trope to a T. How sympathetic and selfish are his goals? And does his goals justify his means of trying to achieve them?

Comic Books

 * This is the whole premise of V from V for Vendetta. Hero or terrorist? Or both?
 * In Watchmen, it's left largely up to the reader to decide whether master plan was truly the right thing to do.
 * Same with Rorschach. He is deliberately left morally ambiguous to let the readers decide whether his extreme methods of fighting evil were necessary or not.
 * The Punisher.

Film

 * The Old Man who is the boss of Omnitech in the RoboCop movies. Even more so in the TV series.
 * Bludworth, the enigmatic coroner who somehow always seems to know what is going on, in the Final Destination series.
 * Medusa, in both versions of Clash of the Titans. Sure, she was a nasty-looking monster who brutally killed the four Red Shirts Perseus brought with them, but then, they were trespassing in her home with the intent to kill her and take her head, so it was hardly unwarranted.

Literature

 * Discworld's Lord Vetinari is a Magnificent Bastard par none, who keeps Ankh-Morporkh's nobles in check through manipulation and intimidation. He is also a former Professional Killer to boot. Apparently, he got into his position thanks to a few well-thought-out assassinations and a firm belief that Humans Are the Real Monsters. He's also the most competent and benevolent patrician the city has ever had.
 * Severus Snape of Harry Potter fame is the poster boy for this trope. His true allegiance is revealed only after
 * Varys from A Song of Ice and Fire. When most of the characters are busy grabbing as much power for themselves as possible, Varys seems to be the only one who actually cares about the realm and it's subjects. While he hates the selfish and power hungry nobles, he is also willing to throw good...well, goodish characters to the wolves. What he wants and why is yet to be revealed.
 * . However, even though this seems as close to a Motive Rant as he's ever going to give us, there is still the possibility that he was lying in some way.
 * Tyrion also qualifies. Has been referred to by the producer of the TV show as "Our Good Bad Guy or Bad Good Guy."
 * Youko Tsukimori from the lightnovel Gekkou. The driving question of the novel is whether or not she's a killer.
 * Most of Tej's family in Captain Vorpatril's Alliance are like this. They are ruthless about defending their patrimony and talk about murder with a creepy casualness. But their Family Business is a comparatively honest one for Jackson's Whole being the management of a space station with sidelines in information brokering and hostage negotiation. The father though was a pirate in his younger days. The Grandma apparently took part in war crimes though that seems to have been mostly record-keeping. On the whole they are a likable bunch who have a certain charm despite their misdeeds.

Live Action TV

 * Mad Men's Bert Cooper is not afraid to resort to blackmail to get his way, and has threatened to lock someone who disagreed with one of his schemes in a closet for a weekend if he didn't comply. Another character believes that he has arranged for someone to be killed before. However, it is never made clear if he intended to follow through with his threats or if he really had that person killed. He always comes off as a kindly, albeit eccentric, old man.
 * Dexter. Season 2 is one long Lampshade Hanging.

Video Games

 * Pokémon Black and White's Team Plasma is this for roughly five minutes. Ghetsis' speech does make sense, but they are the shady organization in a Pokémon game. Then we see one of their grunts kicking a Munna. N does keep his ambiguous status till the end when we learn that
 * First Enchanter Orsino from Dragon Age II.
 * Flemeth from both games. She dismisses rumors without confirmation or denial, and there hasn't been a witness to or onscreen demonstration of her villainy. She's done more to assist the heroes, and her battle with the Warden was only in self-defense. Her power is said to come from demonic possession, yet neither her motives nor methods match any other examples. Morrigan discovers a ritual that supposedly permits her to possess others, but the reasons and results for using it have been cast in question.
 * Her daughter does follow in her footsteps. Despite sticking with the Warden for the entire game
 * Also, the only one who reads the book where the ritual to possess others is mentioned is Morrigan. Who also seems concerned if you had read it before, and is just as morally ambiguous as her mother, which makes the whole thing rather suspicious.
 * Ulysses from Fallout: New Vegas is pretty much this. He seems destined to end up fighting The Courier in some sort of legendary battle. Joshua Graham implies that he . He carries the flag of the Old World on his back, which has connotations, and Old World Blues hints pretty strongly that he wants to . Though audio files from the same add-on detail him rescuing  from the Big Empty and nursing them back to health.
 * Eventually, he's revealed to be a
 * The Spathi of Star Control 2 are a textbook example. They fight for the Ur-Quan and don't seem terribly upset about being party to the enslavement of all intelligent life, but while spineless and shifty they never come close to doing anything evil.
 * The Arilou are a somewhat more benevolent version. They clearly care about humanity, though their reasons for doing so are left ambiguous. They are also The Greys, and have done experiments on us throughout our history, again for purposes they are reticent to discuss. And while they joined the Alliance, they abandoned it as soon as it became clear that the human race was "safe" (i.e., safely enslaved), and were unconcerned with the fate of their other allies.
 * The Orz. Weird Starfish Aliens whose language we can't properly translate. They are quite friendly, and will gladly ally with humanity...but there's something a little bit sinister about them. You meet them in Androsynth (evil cloned human) space, with no sign of the Androsynth anywhere. Demanding answers from the Orz as to what happened is their Berserk Button, and they will attack if you keep bringing it up. The Arilou (see above) insist they are dangerous, and vaguely dole out Eldritch Abomination / Cosmic Horror Story implications. It's all surprisingly creepy.
 * Star Control 3 resolves this question: the Arilou are arrogant and narcissistic but not outright evil, while the Orz are Les Collaborateurs for the game's Big Bad. Of course, Star Control 3 in its entirety is Fan Discontinuity.

Visual Novels

 * Multiple characters in Shikkoku no Sharnoth, including M, Heinz, Arthur, and.
 * Most of the witches in Umineko no Naku Koro ni fall into this category as suits their whims, leaving it quite difficult to tell which if any of them is evil, good or simply in it for shits and giggles.

Web Comics

 * Of the six members of Order of the Stick, Vaarsuvius is the most morally ambiguous. Vaarsuvius is condescending and arrogant and doesn't really care much about saving the world; s/he just joined the Order in pursuit of Arcane knowledge and power, and is trigger happy in his/her use of magic. But s/he genuinely cares for the rest of the Order, and is appalled by Belkar's psychopathy.  There is much debate over hir Character Alignment.
 * Not to mention V had recently shown to be quite... abusive, towards a dominated foe. Though it is a bad guy under V's control, if there were laws on how a dominated enemy can be treated, V would've broken more than a few of them in just two strips.
 * On the other hand, V seems to be drifting more towards the "Good" end of the spectrum lately, courtesy of several My God, What Have I Done? moments.
 * In Girl Genius, it's more about who's all the way barking crazy and who keep themselves in check.
 * Baron Klaus Wulfenbach starts out as a villain who has conquered most of Europe. The reason he did this was to keep in check his fellow mad scientists, who were mostly waging an everyone-against-everyone war on ruins of a halfway-happened Zombie Apocalypse when he crashed the party.
 * Jägers are mostly considered nightmarish monsters outside of their masters' land—where they are, conversely, mostly considered heroes. The sorts of people who chose the transformation and indefinite active military service are obviously dangerous, but "good sports" and honorable in their own strange way. Most are not actively malevolent—one turned out to be, but he "iz no longer a Jäger" (due to breaking his fealty and turning on the masters). Still, their word for a Heterodyne who choose good over evil is "boring".
 * The brothers were "boring" mostly because they insisted Jägers stay at home and don't accompany them on the adventures. Jägers themselves understand that they have quite a reputation and this is a way to avoid scaring people, but didn't like it. Then again, brothers left them behind not only when they saved yet another Damsel in Distress (which perhaps is a good idea), but also when they were in heavy fighting, with a particularly dangerous enemy while Europa was in flames (which obviously isn't). And this indeed didn't end too well, given that only one of the brothers was seen after this in hiding, Europa was still in flames until another guy raised a proper army, and their enemy came back later. This also led to Dimo fishing for reassurance that the incumbent Heterodyne needs him and "boyz" by pretending to shirk his responsibilities.
 * King Radical. His actions could easily label him as a Anti-Villain or even an outright hero. Dr. McNinja, on the other hand, is certain that he's a Villain with Good Publicity, and it's strongly implied that he's planning something big.
 * He is most definitely planning something big. His future self even admitted that he had been. Just what he's planning, and where it stands morally, though, has yet to be said.

Web Original

 * Jhudora from Neopets. Everyone thinks she's evil, but no one has ever been able to prove it.

Western Animation

 * On Galtar and the Golden Lance, Rak and his son, Tuk, are mercenaries who serve either Galtar or Tormack, depending on the circumstances.
 * Zuko from Avatar: The Last Airbender starts out this way. He is the first antagonist, but is given enough sympathy points through out the first season that it is more than a bit hazy on which side of the fence he'll wind up..
 * Its sequel series, The Legend of Korra, follows the tradition but alters the execution - the masked and compelling Amon has a sympathetic backstory told by himself, a number of legitimate points, a mysterious and horrifying ability that he's thus far only used on the deserving and a meticulous, effortless brand of manipulation that throws everything he says and all his motives into question.
 * On Adventure Time, Marceline was this trope in at least her first few appearances, where it was sort of unclear if she was actually going to start killing people or was just messing with Finn and Jake. More recent episodes portray her as basically good, if somewhat mischievous and perhaps capable of true nastiness.
 * Penny from The Mighty B!. Being a Bitch in Sheep's Clothing, she teams up with Portisa and Gwen to make Bessie eat Zukini.
 * Principal Pixiefrog from My Gym Partner's a Monkey.
 * Nester's Mother, Momma from Scaredy Squirrel.
 * MacBeth in Gargoyles. He's quite ruthless about achieving his goals but his main goal is to destroy Big Bad Demona (and thus himself) and he has his share of Pet the Dog moments.

Other

 * Shockwave, in the Transformers: TransTech/Transformers Animated script-reading play, "Bee in the City". He describes himself as "morally ambiguous".
 * In Warhammer 40,000 this is the Alpha Legion's hat, down to the last man. While they sided with Horus during the Horus Heresy, they were apparently attempting to fulfill a prophecy in which Chaos would be destroyed permanently (at the cost of the human race albeit). After the Heresy, they're the only legion not present in the eye of terror, and are generally planning something...