There are times when the heroes can't come out on top—and moments where the villains must have their day in the sun. There are countless examples of these amazing endings across the many medians of storytelling, whether it be Thanos, who achieved his goal in the MCU, or any form of animated Berserk series.
The same holds of shojo anime as well. There are times where the villain should win to help create a better story. In some cases, series did that, and in others, they didn't pull the trigger when they should have.
10 Villain Won: Kyubey Still Gets What It Wants From Madoka (Puella Magi☆Madoka Magica)
The best example of a villain winning in a shojo anime is Puella Magi☆Madoka Magica with Kyubey. After everything that Madoka goes through to try to break the creation of the magical girls, none of it matters because Kyubey still gets exactly what it wanted in the end.
It got Madoka to sign the contract and continues to stave off the greater threat to its species. It's one of the most downer endings in an anime.
9 Villain Should Have Won: Su-Won Should Remain King Of Kouka (Yona Of The Dawn)
As a villain, Su-Won is an interesting one. He committed an awful act by killing Yona's father to become the king of Kouka in Yona of the Dawn, but he's not that bad of a person despite this. He still holds feelings for Yona and Hak, not wanting either of them to be harmed.
He even purposely hides the fact that Yona is still alive from his followers, so they don't look for her. Beyond just that, he's also been a good influence on Kouka as king, allowing it to maintain prosperity.
8 Villain Won: Rue Gains The Love She Always Wished For (Princess Tutu)
As a villain, Rue was more than a little sympathetic. She wasn't out to conqueror the world or bring pain and suffering to anyone. She was a character who only wanted one thing, and that was the love of Prince Mytho.
The way she goes about it is poor, especially helping her false father, but in the end, she manages to gain the love of her prince. It's a villain victory that surprisingly feels good, leading to a heartwarming ending.
7 Villain Should Have Won: Shizuka Hio Should Have Got Some Measure Of Revenge On Rido (Vampire Knight)
Shizuka Hio wasn't Vampire Knight's main villain and acted more as the first antagonist of the series. She's the one who slaughtered Zero's family, leading him to hate pureblooded vampires. In reality, she was a victim of manipulation by both Kaname and the main antagonist Rido Kuran.
Kaname released her from prison so she'd kill Zero's family. Rido purposely had Shizuka's lover murdered if any villain deserved some matter of victory, even if playing a small role in defeating Rido, Shizuka.
6 Villain Won: There Is No Love To Be Found In The Story (Angel Beats!)
Love is at the core of Angel Beats!—both from the villain perspective and the protagonists. They are all trying to find a way out of limbo, to find a level of peace with themselves. Slowly, all of the members begin to pass on, leaving behind Kanade and Otonashi as the final two.
Otonashi wants to stay behind as a guardian to those that arrive and wants Kanade to stay behind since he loves her. As that declaration gets made, she starts to pass on as she's finally at peace, ending the anime in a very bittersweet fashion.
5 Villain Should Have Won: Akura-Ou Should Have Rekindled A Relationship With Tomoe (Kamisama Kiss)
The goals Akura-Ou has in Kamisama Kiss are murky at best, as for most of it. He seems to want to understand better love and why Tomoe would choose a human over him.
His growing feelings for Nanami are the main plot point and make his eventual sacrifice to save a human rather touching. That said, it would have been nice if he'd managed to rekindle his relationship with Tomoe before then, further cementing the change he underwent as a character.
4 Villain Won: Love Frees Takkao From The Clutches Of Villainy (Pretear)
Pretear is a magical girl series that centers around love, as many do. Himeno and Hayate slowly become closer throughout the series, causing the ire of Takkao, who always desired to be with Hayate. This jealousy and anger morph her into the Princess of Disaster, the antagonist of the series.
While she does a few villainous things, she's always been driven by love, and by the end, that's exactly what she receives by way of Sasame's feelings for her.
3 Villain Should Have Won: Sho Being The Bigger Celebrity Would Get Kyoko To Focus On Her Feelings For Ren (Skip Beat!)
The premise of Skip Beat! is both great and uniquely executed as a series. Kyoko is deadset on getting her revenge on childhood friend Sho, who saw her as nothing more than a servant rather than a friend. She's determined to become a bigger star than he is, thus taking away the one thing he valued more.
While that would be great, it's consumed her life, and failing at it would allow her to realize her feelings for Ren, giving everyone a good ending.
2 Villain Won: The Aliens Go Home With The Mew Aqua (Tokyo Mew Mew)
Through most of the series, the aliens were at odds with the Tokyo Mew Mews. They were trying to retake the earth from them, viewing it as their birthright and true home.
Through continued battles, the core three of Quiche, Pie, and Tart come to respect the Mew Mews, even teaming with them to defeat Deep Blue in the end. As the series ended, the Mew Mews granted them a Mew Aqua, allowing them to make their home planet as beautiful as earth.
1 Villain Should Have Won: Sailor Moon Never Should Have Stood A Chance Against Sailor Galaxia (Sailor Moon)
In most cases, the villain winning would bring about a better ending, but that wouldn't be the case with Sailor Galaxia's victory. It would have been a bleak end to an otherwise uplifting series.
The issue is that Galaxia was built up so much in her season that there should have been no way she should have been beaten by Sailor Moon alone. The fight was far better explained and handled in the manga than it was in the anime.
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