For years, writers have been crafting conventional stories wherein the bad guys lose and the good guys win. It's not a terrible plot line, since everyone loves a happy ending, but that doesn't mean the heroes can't take few lumps on their way towards victory.
In some anime, the good guys don't just lose to the bad guys, they get beaten to to an unrecognizable pulp. Some of the smartest and most underrated anime villains manage to get the drop on their heroic adversaries and kick 'em to the curb. If you're someone who always roots for the protagonist, get ready to have your heart-strings tugged at mercilessly.
The Arrancar named Grimmjow Jaegerjaquez humiliates Ichigo Kurosaki twice in battle during the Arrancar Invasion in Bleach. In their first encounter, Grimmjow impales Ichigo's best friend Rukia Kuchiki with his hand, then toys with the Soul Reaper for the remainder of their bout. While Ichigo does land a successful attack on Grimmjow — which leaves a visible scar on his torso — he fails to overcome his enemy, and is only spared because Kaname Tōsen intervenes and calls off the fight.
Even though Grummjow is missing an arm during their second battle, Ichigo still can't outmatch him. For a while, Ichigo has him on the ropes thanks to his Hollowfication powers, but once it breaks, Grimmjow manages to snatch victory a second time. This time, Ichigo is saved when Rukia temporarily freezes Grimmjow, giving the hero a chance to escape.
The Italianate mob boss of Baroque Works, Crocodile, holds a special spot in One Piece history. He effortlessly defeats the rubber pirate Monkey D. Luffy not once, but twice during the Alabasta arc. What gives Crocodile the upper hand in his fight with Luffy is his Devil Fruit powers: he can turn his body into sand, allowing him to avoid taking physical damage.
Even without his powers, Crocodile would still be a formidable foe. His strategic mind and large poisonous hook are enough to make quick work of anyone who gets in his way. If not for pure luck, Luffy would have died during any of his three encounters with Crocodile. Even in their final bout, Luffy only comes out on top because of good luck. If the blood from Luffy's cut up fist didn't act as a suitable substitute for water, there's no way he could have exploited Crocodile's aversion to H20 to achieve victory.
Spike Spiegel is one of the most bad*ss anime characters around, there's no doubt about it. However, even tough guys like Spike go down every once in a while, and this is especially true if the enemy is a psychic killer clown infused with the cruelty of a child.
In what is perhaps the most terrifying and psychedelic episode of Cowboy Bebop, "Pierrot Le Fou" begins with Spike witnessing Mad Pierrot horrifically murder an official and his bodyguards outside a bar. Spike engages the assailant in a gun fight, but all efforts to fill Pierrot with lead prove futile, as he has a bulletproof forcefield covering his body. Just before Pierrot finishes Spike off for good, a toy cat triggers a painful memory for the killer, which gives the hero time to escape with his life.
The Dark Tournament arc of YuYu Hakusho is crucial to the emotional development of Yusuke Urameshi. For alll his sardonic retorts, Yusuke finds himself speechless once he sees Toguro come back from the dead to reveal his true strength. Toguro faked his death during Yusuke's last mission, so he could collect the riches from a bet he placed against himself. He gives Yusuke an ultimatum: participate in the Dark Tournament, or see all his loved ones die.
In the anime, Toguro intimidates Yusuke by destroying an unfinished building with only 60% of his power. Throughout the tournament, Yusuke struggles to reach a power level high enough to equal Toguro's, but even after a ton of intense training, he struggles to take down the villain (who's still holding back his real power). Yusuke only manages to defeat a fully powered up Togouro after he sees his enemy kill his best friend, Kazuma Kuwabara,