- There Will Be Brawl: There is no good or evil. The 'good guys' are drug dealers, strippers, or Fallen Heroes, the 'bad guys' actually have a plan to improve the quality of life in the Mushroom Kingdom, and the cops are corrupt and trying to usurp the throne. The only one with a clear designation is Kirby...who is a psychotic cannibal, a la Hannibal Lecter.
- There's also Red, the only character who is truly good. Which makes it all the more sad (and fitting) when he dies by Pikmin bomb
- Red vs. Blue. The default characterization seems to be 'incompetent jerk', with variations lying mostly in the type and degree of incompetence and/or jerkassery.
- The gray becomes even more clear when the Freelancer backstory starts to be brought out in seasons 6 through 10. On one hand, you want to root for the Freelancers. On the other, they're doing a lot of morally questionable things. Even those who are clearly "bad guys" (Sigma, the Director, CT, etc.) have a lot of nuance once you learn why they do the horrible things they do, and in the end, it's hard to say who's really good or bad.
- Dark Dream Chronicle. One side has the Laughing Clown and Darkness as two of its primary members. The other is trying to warp humanity for their Cause and are more than willing to use violence to get there. Oh, and it's led by the Slender Man.
- "Champions of Meridell" in Neopets is the first war between Meridell and the Darigan Citadel, after the greedy king Skarl stole the orb of prosperity from the originally Perfect Pacifist People of Darigan for his own glory and power, causing them much misery and pain and mutating them into vengeful monsters who try to destroy Meridell. There are both good and evil on both sides, with the heroic Jeran serving the villainous Skarl, and the anti-villain Darigan seeking to return the orb to his people.
- In Pokegirls, humankind survives entirely due to a system of raping and brainwashing the eponymous female subspecies... which are themselves notorious for rape and murder.
- Neither side in The Abridged Series Sonic the Other Movie is clean. Sonic only fights evil because it's fun, and villain Dr. Robotnik's evil plans to kill Sonic are simply to remove the obstacle preventing him from taking over the world and turning into a utopia.
- While Doug's writings of the anniversaries are a bit blacker, The Nostalgia Critic's show runs on this. Critic's a Psychopathic Manchild but tries to be a decent human being, Sage-as-Satan is much less scary than he is as his normal self in other series, Big Good Santa Christ can hold a mean grudge and even major troll Douchey manages to show a bit of heart when he feels pity for Critic at the end of the third fuck-up list.
- Dead Fantasy. Sort of. Monty Oum always said right from the start that the series isn't about which side wins, or which is better, or which is good or bad, and that everyone should just focus on the fighting.
- Comes up in RWBY, and Played for Drama. What happens when you take two people who are supposed to be friends and colleagues and have circumstances beyond their control place them on opposite sides of a conflict like this? Just ask Weiss and Blake. Weiss is the heiress of the Schnee Dust Company, and Blake is a former member of the White Fang terrorist group. Weiss and her family have been targeted by members of the White Fang for as long as she can remember, and it's also implied that her ill-tempered father took his frustrations out on her, but where Weiss is wrong is that her personal prejudices cross the boundaries onto all Faunus in general. While it is true that Blake was a member of the White Fang, she left because they began terrorising and killing innocent people, which she objected to. Despite this, she still feels compelled to defend their cause and their actions. Of the two, Blake is perhaps the more sympathetic, but Weiss remains a Tragic Bigot.
- The story's main overarching conflict at first averted this, being pretty much Black and White Morality. However, later on the story becomes much more nuanced, with the villains being revealed to have sympathetic qualities and the Big Good having a shady past, and morally complex characters like Raven Branwen (who is basically a Byronic Anti-Villain).
- In Space Janitors, a parody of the Star Wars universe, rebels are portrayed as egotistical adrenaline junkies. Meanwhile, imperial citizen are portrayed as very happy to completely buy into the propaganda of the empire.
- Doctor Locklear argues about this with police officer Bernadette in Mindgames. Yes, he tortures and kills people, but considering his victims are released convicts or people ruled not guilty by the flawed legal system, and that the one time he saved a criminal he lost his wife and unborn child, Locklear sees what he does as completely justified. He convinces Bernadette enough that she refuses to shoot him after she gets her gun back and ends up resigning instead of telling the other police she found him, which was what she set out to do in the first place.
- Backstroke of the West: For all their heroism, the Hopeless Situation Warriors perform some rather unsavory actions for the sake of their goals, and the villains are either Well Intentioned Extremists at best, like The D, or have redeeming qualities, like how Space General is a Benevolent Boss.
Grey And Gray Morality / Web Original