Although Pretty Cure makes it a point to give villains a chance, they still have those who don't get any.
- In Futari wa Pretty Cure, Gekidrago trying to kill Cure Black's little brother in front of her, and Poisony not only mind-controlling Those Two Guys into believing they are the Cures, but also into either attacking the real Cures or deliberately putting themelves in danger so Honoka and Nagisa would get distracted in battle trying to save them. Both of these are not very impressive in scale compared to later MEH's in the franchise, but it was the first especially despicable act of villainy the franchise ever saw, and the former is especially notable in that it resulted in Cure Black killing Gekidrago.
- In Futari wa Pretty Cure Splash★Star, Lord Akudaikahn condemning Michiru and Kaoru to a Fate Worse than Death. Gohyaan got his when he captured and tortured Flappy and Choppy, or when he betrays his master, revealing himself to be the main villain.
- Yes! Pretty Cure 5 (and Go Go):
- Girinma crosses it when he turns Urara's memento of her deceased mom into a Kowaina. Considering the importance of dreams in this series, though, it's possible that he crossed it even earlier—in the very first episode, even!—by mocking Coco's dream in a most callous fashion.
- Kawarino goes over the line when he backstabs his former superior Bloody just because he 'served his purpose' of seeing the Dream Collet completed and sends him to the depths of Hell. He gets his comeuppance when Bloody ends up dragging him down with him. Another potential point one can point at is when he forces Hadenya to wear a black mask, despite her trying to tell him she doesn’t need it.
- Shadow crosses it when he/she/whatever call Dark Dream useless and dying like a dirty traitor after she takes a hit meant for Cure Dream.
- Fresh Pretty Cure!:
- Klein crosses it by killing Setsuna just because she ultimately saw Love as a true friend. Also, Northa backflips over it shouting "Woohoo!" in her attempt to brainwash Setsuna back into Labyrinth so Pretty Cure will be one member short. No doubt Cure Peach is not going to stand for it.
- Moebius crosses it for sure when he orders the deletion of Soular and Westar, two of his most loyal servants, along with Cures Passion and Berry just because he felt they were no longer useful to him. Love must've been quite a saint that she still thinks that after all those, Moebius still deserve to 'find his own happiness'. He does, and he decided that his happiness is dead Precures.
- HeartCatch Pretty Cure!:
- Dune crosses this when he kills the Heart Tree, causing a worldwide near-apocalypse.
- If Dark Precure didn't cross the line by Murdering Cologne and depowering Cure Moonlight by stealing half of her Heart Seed, no doubt it was by ransoming Chypre and Coffret over the Heart Seeds. And that was just her debut.
- Smile Pretty Cure!/Glitter Force: Joker/Rascal is already far over the line and cements it by inflicting the Ball of Neglect/Dream Ball on Candy and eventually the Cures/Glitter Force. And that's not going into how, in brainwashing them and Akaoni/Brute, he was behind Wolfrun/Ulric's vendetta against Akane/Kelsey and everything she cared about, including the destruction of her charm and the subsequent attempt on Miyuki/Emily's life, and Majorina/Brooha's attempted yet very seemingly murder of two of Nao/April's siblings.
- Doki Doki! PreCure/Glitter Force Doki Doki
- Regina's involvement in the destruction of Trump Kingdom/Splendorius may not count after all, but Bel is revealed in episode 46 to have tried to corrupt Marie-Ange, which ultimately caused her to split in two and become Aguri/Natalie and Regina.
- Also, Marmo steals Sebastian's morpher and was willing to throw someone off a building and making it look like she's saving her.
- Not to mention that Leva and Gula send evil seeds around the city to turn people into Jikochuus/Disdains, and after their Fusion Dance, destroys the Lovely Mirror Pad.
- HappinessCharge Pretty Cure!:
- Hosshiiwa: Wounded Gazelle Gambit against the Cures in her debut battle.
- Phantom: Capturing Cure Tender. After all it's in his job description.
- Queen Mirage: Brainwashing Cure Tender.
- Turns out Deep Mirror was behind everything, which makes him pretty much responsible for everything.
- Speaking of non-redeemed villains, the Non-Serial Movie villain Black Mask goes over the line by using a Delicate and Sickly girl as a pawn in his game against Pretty Cure.
- Go! Princess Pretty Cure:
- Close crosses it by turning the Noble Academy house of dreams into a Zetsuborg.
- Dyspear's moment comes either when she:
- was revealed to have not just brainwashed Princess Towa into becoming Twilight but also attempted to murder her by using the Black Perfume to drain her life energy. In case you didn’t know, Twilight/Towa is thirteen years old!
- psychologically tortures Towa by saying she lost her dream when she entered the forest.
- threatens to put the Cures in the cage of Despair. Cure Scarlet was absolutely not amused at that.
- decides to attack Noble Academy instead of Hope Kingdom and turns Lock’s corpse into an undead puppet.
- The aforementioned Lock crossed the line by capturing Kuroro.
- Also the Non-Serial Movie villain Warp seals away Pumplulu and erases her parents' memory of her.
- Maho Girls Pretty Cure!:
- Orba crossed the line by blackmailling Chikurun to spy on the Cures, and after this is exposed Shakince was willing to hurt the cures even though Chikurun was promised that it would not happen.
- Benigyo was willing to attack children for something as petty as imagining her as Santa.
- Deusmast crosses this territory by merging Mahoukai and Nashimahoukai.
- KiraKira★Pretty Cure à la Mode:
- If it wasn't his manipulating of Julio and Bibury, Noir crossed it with his attempt on Ciel's life but hits Pikario instead. Keep in mind that although deaths have occurred in the world of Pretty Cure and Pikario gets better, this is so far the closest the franchise had for a Hero Killer (not to mention the hero is a minor).
- Elisio crosses it in Episode 46 and 47 when he captures Noir and Lumiere. and uses their powers to turn the whole place into his own police state and burn every sweet as garbage.
- Also the Non-Serial Movie villain Cook exploits Jean-Pierre Zylberstein in her evil plan to turn Earth into a sweets planet.
- Star★Twinkle Pretty Cure: The Notraiders might be a little more silly than previous villains, but their members have done some atrocious things thus far:
- Tenjou is willing to turn children into giant Notraiders, just see the first ep where she does that.
- Kappard's MEH is firing water against a Planet Plasma person, knowing it would destroy him. In short, attempted murder.
- While only a minor character, it's still worth noting that Don Octo crosses this in #36 by setting up Blue Cat and Mary Ann, a cop, to be incinerated by lava.
- If it wasn't destroying Garuoga's planet and luring him and the others into the Notraiders, Darknest crossed this by revealing herself as the Ophiuchus Princess and abducting the other twelve Princesses and Fuwa after laying waste to the Star Princess Palace.
- Healin' Good♡Pretty Cure:
- Batetemoda crosses it when he tries to kill Latte, all with a gleeful smile on his face. Perhaps unsurprisingly, he is killed in the episode after that.
- Daruizen crosses it by stabbing Nodoka with a Mega Part, summoning Kedary.
- Shindoine crosses it when she chooses to infect a child with a Nano Byo-gen. This was after she injected herself with a Mega Part to power herself up in an attempt to impress King Byo-gen.
- Guaiwaru crosses it when he comes up with a scheme to become the new King Byo-gen and infects all of the city by summoning an army of Megabyo-gens. Sadly for Guaiwaru, he doesn’t get to keep the power long as the King returns and absorbs him to regain his power.
- Tropical-Rouge! Pretty Cure: Butler crosses it when he turns Chongire into a Yaraneeda against his will. If he didn’t cross it then, he crosses it when he decides to continue the plan to try to open the Fool's Casket, even after the Witch is convinced to reform.
- Delicious Party♡Pretty Cure:
- Narcistoru crosses it when he shuts down Spiritoru after his third failure to beat the Cures.
- Godatz crosses it after his reveal that he's actually Fennel when he beats the Cures out of their forms and attempts to murder them with a cold expression on his face.
