"That's not what a 'sick burn' is, you jerk!"
It takes a special kind of villain to commit unforgivable acts in what is, on the surface, a series about capturing and befriending colorful and diverse creatures.Pokémon: The Series
- Damian, the former trainer of Ash's Charmander, crossed it when he refused to come back to Charmander (simply because he considered it to be weak) when it began to rain and Brock told him that rain would make Charmander's tail flame go out and it would die. He crosses it even further when it's revealed he couldn't care less about putting in the effort of training Charmander himself, outright saying that raising a Pokémon is a boring waste of time.
- Pokémon Hunter J, in the "Pokémon Ranger and the Kidnapped Riolu" two-parter, really shows her cruelty when she tries to kill Ash (a 10-year-old boy) several times. First she orders her Salamence to burn the surrounding forest and fire Hyper Beam directly at him, then has her Drapion squeeze him tightly, and finally ejects him from her ship at great height. She also says that she wanted to punish Ash personally and took pleasure in trying to kill him and everytime she attacks Ash she is shown with a Slasher Smile.
- Cyrus from the Diamond and Pearl arc of the Pokémon anime crosses this line when he orders Mars to blow up Iron Island, which is full of Pokémon and people living there - sporting a Slasher Smile whilst giving that order.
- Kodai from Pokémon: Zoroark: Master of Illusions crosses this when he electrocutes the baby Zorua right in front of its mother Zoroark. Unlike the other horrific things he did, this is really the first time he's shown doing something terrible that didn't have anything to do with his plan, as Zoroark stopped attacking the moment she saw he had Zorua. He even comes right out and says he enjoyed it directly after that.
- Lord Ghetsis of Team Plasma in the Episode N arc crossed the line when he ordered a mind-controlled Reshiram to incinerate everyone currently at the White Ruins...which included several members of his own team! Team Rocket even calls this out as being self-centered and deplorable.
- Lysandre crosses it when after Z2 was freed and his weapon dismantled, he opts for a contingency plan to have a Zygarde-shaped Megalith rock, powered by Mairin's infected Chespin (coldly subverting Lysandre's previous Pet the Dog moment where he agreed to look after it and keep it alive) act as his new weapon and have it eat up all the power of the Anistar Sundial so that it would unleash energy that would eradicate all life on the planet, and he's willing to do this solely out of spite and resentment for the world and the people who obstructed his genocidal plans.
- Viren from Sun and Moon proves himself to be an irredeemable scumbag when he orders his Electivire to launch a Thunder attack on Mimo, Kiawe's little sister, for protesting against turning their family's ranch into a resort hotel. Turtonator blocked the attack and was KNOCKED OUT.note If it could KO a Pokémon that's resistant to Electric-type attacks, imagine what kind of damage it could have done to a frail, little human girl.
- Dr. Zed from Pokémon: Secrets of the Jungle crosses it when he causes the car accident that kills Koko's parents after they tried to hide the research of the Spring of Healing.
Pokémon Adventures
- While the Elite Four's plan for human genocide is horrific, Agatha's part in it puts her over the line because she lacks the others sympathetic motives for it - she simply desires greatness and to prove the supremacy of strong Pokémon trained by elite trainers in order to spite Professor Oak. She also gleefully expresses her desire to see both Oak and his grandson Blue dead.
- Sird had her Darkrai turn the four Kanto trainers plus Silver into stone and left them there for dead.
- Charon and Giratina nearly killing Dia, with Charon having the gall to laugh in a devastated Pearl's face over it.
- Ghetsis's original Moral Event Horizon crossing plans from the games are still here, but on top of that he has six Unova Gym Leaders captured, beaten up/tortured, and hung up on crosses in order to make a statement of Team Plasma's superiority, and then tries to have his Hydregion kill Black with fire on the spot. When normal trainers interfere and stand up to Team Plasma, he orders for them to be killed too. And of course, there's him trapping Black inside the Light Stone for two whole years out of spite.
- Colress' crossed it with his part in in Team Plasma freezing Castelia City and many other cities in Unova, as Kyurem is tortured inside of his machine and put under Mind Control thanks to his science, and he's positively gleeful at the results of the freezing and is excited at the possibility of freezing more targeted locations.
- Even putting his plan aside, Lysandre certainly crossed it by locking Emma's expansion suit and forcing her to fight 'til it almost gets her killed.
- Branch Chief Faba having pushed Mohn into a Ultra Worm hole so that he'd be out of the way and Lusamine, driven into despair, might fall into his arms instead.
Pokémon: Diamond and Pearl Adventure!
- Charon accomplishes this before he even shows up, by ordering some of his mooks to suicide bomb the Pokémon League tournament.
Video Games
- Cyrus from Pokémon Diamond and Pearl, whose plan was literally to control the powers of time/space and use them to wipe out the entire universe and all life in it so that he could then become a deity and recreate reality as he saw fit, which would be a reality without spirit, meaning all living creatures would now exist with no emotions, free thought, or free will. Granted he believed this to be in humanity's best interest, but it's still a sick and horrifying goal that he wanted to force on others. The lengths he took in the name of this goal were not pretty either, especially his plan with the Galactic Bomb and the torture of the three lake Pokémon in order to create the Red Chain.
- Mad Scientist Charon, who was in charge of making the Red Chain, shares in that last one. And he had his own terrible plan to use Heatran's destructive powers to terrorize entire civilizations in order to extort money from them that thankfully never took off thanks to the player character's interference.
- Pokémon Black and White: Ghetsis, Ghetsis, Ghetsis... Let's see, he neglected his own boy, left him among abused Pokémon to ruin his perception of the world, raised him to believe Pokémon should be separated from humans, and gave him control over a group that only knew of his ideal. But that he has the audacity to abandon the kid after his failure to perform, call him a blasphemy upon mankind for the very way he raised him, and go against everything he ever taught him just for self-profit? Yeah Ghetsis, you can rot in jail for the rest of your life. Black 2/White 2 reveal that N is not even Ghetsis' biological son. He's just some orphan/runaway that Ghetsis found one day and decided might be useful to him in some way.
- In Ultra Sun/Ultra Moon, Lysandre has the ultimate weapon constructed within Aether Paradise and threatens to use it to annihilate everyone unless you defeat him in battle, following a Sadistic Choice that makes you activate it.
- Faba, a Child Hater and Smug Snake in his own right, soars across the line in Ultra Sun and Ultra Moon when he sells out the Aether Foundation to join Team Rainbow Rocket just because he wanted to further his own career.
- Pokémon Legends: Arceus: Volo crossed it when he told Giratina to kill the player. And after his defeat, his reaction makes it clear that he's still unrepentant over it. It's completely a wonder why he receives no comeuppance from anything or anyone, especially in a franchise known for gleefully punishing other villains of similar magnitude with Fates Worse Than Death.
- Pokémon Scarlet and Violet: While it's left ambiguous whether Professor Sada/Turo was evil, the Paradise Protection Protocol AI they designed definitely shows the depths of their obsession by locking the heroes' Pokéballs and sending out a feral Koraidon/Miraidon to attack them.
- Most members of Cipher from Pokémon Colosseum and Pokémon XD: Gale of Darkness has crossed it in one point or another just by Mind Raping Pokémon and turning them into killing machines, committing all sorts of violent, petty and underhanded acts unparalleled by any other villain in the video games (yes, including Ghetsis) and their de facto leader Greevil eventually wanting to use these violent and unstable Pokémon for global domination. And then there's Ardos, one of Greevil's grandsons, who crossed it when he asked Greevil to blow up Citadark Isle to kill the protagonist and every other Cipher member within the facility so they can run.
- Then there's Purple Eyes from Pokémon Ranger Guardian Signs. Before we even learn he exists, he's beaten Rand within an inch of his life and kidnapped both his wife and daughter. Later, he beats the daughter up, too! He kept getting worse up until he thought it would be a good idea to bark orders at Arceus—at which point he dearly paid for it.
- From Pokémon Mystery Dungeon: Explorers: In the endgame, Darkrai crosses it by trying to trick the player into committing suicide and manipulating Palkia to kill them by trapping him too in a nightmare while impersonating his Good Counterpart. Afterwards, he reveals that he's the one responsible for the game's cataclysm.
- In Detective Pikachu, Roger Clifford crossed it by wanting to send the Pokémon Carnival into chaos by poisoning the Pokémon in Ryme City with R and trying to kill Tim Goodman in the final chapter of the game.
