It's Type Moon and Kinoko Nasu. With the Crapsack World (or crapsack alternate world) set in, you are sure to find utterly despicable characters that make you grind your teeth in anger and hatred when they make an appearance.
- Fate/stay night features a great number of villains, but nearly all have some sympathetic quality, even Kirei and Gilgamesh (or at least something that makes them undeniably cool villains). These three do not:
- Shinji Matou, pictured here, is Sakura Matou's abusive brother who is unpleasant on a personal level. A smug braggart, Shinji also mistreats his own servant, Rider, and cares nothing for her well-being, and he desires to force Rin Tohsaka to bow to him and satisfy his lust towards her. In the Heaven's Feel route, he's also revealed to be a rapist who primarily targets his sister, already a very sympathetic character. Arrogant and sexist, Shinji Matou lacks the interesting qualities of his rivals, instead being a pathetic loser who always gets outwitted. It says something that, in nearly two decades of vile villains in the Nasuverse, this one high school kid still manages to be the most near-unanimously hated character. It's even lampshaded in Carnival Phantasm where Sakura outright says that his only positive quality is making everyone around him look good.
- Zouken Matou is Shinji and Sakura's abusive grandfather and the antagonist of the Heaven's Feel route. Being directly responsible for molding Shinji into an abuser for his own purposes, Zouken continually mentions how little he cares for him, while committing all kinds of atrocities for the sake of keeping his immortality. He afflicts Sakura, his own granddaughter, with sexual violations via his own magic worms, making her a broken shell of a girl, and orchestrates the deaths of his rivals in the most sadistic manners possible. In Fate/Zero, he torments Kariya, his own son, out of pure sadism. Zouken may have once been a well-intentioned man, but he has now become a monster worse than even Kirei.
- The 2014 Fate/stay night [Unlimited Blade Works] TV adaptation gives an expanded character to Caster's summoner and first Master, who in the VN is supposed to have been a boring coward, but is nameless and never appears onscreen. Atrum Galliasta is Adaptational Villainy personified, with zero redeeming qualities and even less sympathetic than Shinji, if that's possible. He sacrifices orphans/kidnapped children for mana and doesn't like that Caster can gather much more mana without killing anyone because it shows that she's a better mage than him—and possibly because her method doesn't involve killing anyone—he hits and insults his far more powerful Servant and uses poorly-thought-out methods to enforce her obedience, and he's a Straw Misogynist on top of everything else, keeping a literal harem and using only girls for his mana sacrifices. He's present mainly to make Caster look like a saint.
- Fate/Apocrypha: Celenike Icecolle Yggdmillenia is the vilest member of her family. A sadistic Master who delights in torturing whoever she comes across, she loves taking the noble qualities of a Servant and then violating said nobleness; and in comparison to her other Yggdmillenia clan members, she's the only one who really doesn't have any redeeming qualities, to the point that no tears are shed for her when Mordred lops her head off.
- Fate/Grand Order, with various Alternate Universe shenanigans, you will find despicable characters, and by the gacha nature of the game, some of them may even find a way to your roster.
- Christopher Columbus, known as the Rider of the Resistance that debuted in the Agartha Singularity. Unlike other Servants, Columbus instead got an overblown Historical Villain Upgrade, having the negative rumors and traits about him flanderized: He's a two-faced self-serving bastard that masks his own dark, selfish desires with positive traits such as being an inspiring Determinator, while also holding high values that usually disgusts normal people (for example: Slavery should be promoted because it's much more profitable, even if the age of slavery has been long gone). While he is summonable, the game and narrative makes no excuse that Columbus is an utter bastard you're supposed to dislike. Being portrayed as an old man instead of having a Gender Flip like other Servants might help push this trope further too, and while he doesn't promote slavery as often, he still does everything in the name of profit thus most of his actions tend to leer into another unsavory role of a Con Man.
- When it comes to non-Servant, there's also the Demon God Pillar Flauros, though you know him more as Professor Lev Lainur. What differentiates him from other Demon God Pillars are that he begins the game by gruesomely killing Olga Marie Animusphere to non-existence, all while taunting how pitiful she is, and he spent the rest of his time being a supreme Smug Snake, always babbling about how doomed you, the players, are in the face of him and the other Demon God Pillars; and makes unpleasant Slasher Smile too while he's at it. And when eventually his master, Goetia, developed his own character and other Demon Pillars gain their own quirks, Flauros basically stays in square one forever, still the same Smug Snake as ever. This results in fans cheering when Altera butts into the Septem Singularity to kill him, and it's considered one of the few good things of the Singularity when it's considered problematic. And additionally, in the Solomon Singularity, after the fans were done farming with Barbatos, they went straight to obliterate Flauros with full intent of making him pay for the gruesome murder of Olga Marie and for being a smug ass to the end.
- The Caster of Limbo (a.k.a. Ashiya Douman) revels in being a Smug Snake supreme, making the lives of everyone in the Shimousa Sub-Singularity miserable and takes extra delight in the suffering of Katou Danzou as his 'puppet'. Even his fellow Swordsman of Carnage, Saber Empireo/Yagyu Munenori, doesn't have high opinions on him and killed him when he tried to enact his revenge on Musashi, but he lived and revealed that all his servitude was an act, his true loyalty was to the Alien God and the whole thing was just a prelude he prepared for the Lostbelts. He then gleefully made some peaceful Lostbelts into hell on Earth (the Yuga-Kurukeshtra, especially) and gives a MUCH more revelling towards the sufferings he caused, and in his last stand at Part 2 Chapter 5.5: Heian-Kyo, it turns out that he does all those for the sole reason of surpassing his eternal rival Abe no Seimei and satiating his pride, which Seimei used to the heroes' advantage by not appearing in physical form, allowing him to be beaten for good. After being summonable, he might have claimed himself to be free from the Alien God's link, but all of those petty and despicable actions are still on his own volition.
- God Arjuna is easily the least sympathetic Lostbelt King as while is far from being the most violent or ruthless Lostbelt King, he is almost completely without sentimentality and is utterly disinterested in ruling his world directly. This allows him to coldly eliminate scores of his citizenry for the most minor of infractions or blemishes, including superficial injuries in his pursuit of perfection. It's telling that he doesn't fight his climactic battle for the sake of his timeline like all the other Lostbelt Kings before him, but out of hatred and bitterness towards his old rival Karna.
- The Lostbelt versions of the Dioscuri twins are easily the least sympathetic villains in the Atlantic Lostbelt. Due to humanity (inadvertently) weakening Pollux's Divinity and removing Castor's Divinity, they decide to vent their frustrations by murdering humans. This gets quickly called out as Disproportionate Retribution by many of the characters. While their playable selves avert this as the playable version of Pollux is a Nice Girl, and she acts as a Morality Pet to the playable version of Castor, Pollux's Lostbelt self acts as a Yes-Man towards Castor's Lostbelt self that fully supports Lostbelt Castor's murderous tendencies; allowing them to lack any sympathy from the players.
- After the conclusion of the British Lostbelt, Aurora makes herself to be one of the most despicable characters within the Lostbelt, and that is saying a lot since the other faeries aren't very beneficent themselves. Originally presented herself as a Reasonable Authority Figure but turns out to be a Bitch in Sheep's Clothing who just wants to be the most beautiful and brilliant faerie of them all, and wants everybody to love her even though she loves nobody but herself. She went on to mastermind the deaths of Morgan and Cnoc na Riabh as she sees them as threats to her beauty and her brilliance, and when her trusted assistant Coral starts questioning Aurora about everything she did, Aurora simply turns Coral into a bug and squishes her for questioning her. Also, while she ends up giving Tam Lin Lancelot/Mélusine sentience when Mélusine is supposed to become a mindless engine of destruction, she's also very manipulative of the Tam Lin, and her giving sentience to Mélusine was not out of pure intentions but to keep her impression of “being perfect” going on. All in all, she is a character that had her death in hands of Mélusine coming for her.
- While Aurora's presence and Hate Sink-ness largely overshadow his, the conclusion of the Lostbelt also finally cement everybody's least favorite Crypter, Beryl Gut, as a definitive one, which is after he had Kirschtaria Wodime, after revealing his more noble intention for humanity, killed because he didn't find his idea of new world 'fun enough' for him. While he kept up an Affably Evil aura beforehand, turns out that he's only in Team A and getting his Lostbelt because it fits his view that he can keep doing his hobby of murdering people. He also tricked Baobhan Sith to use a life-costing curse for him, which adds up to her descent to madness. And the Lostbelt also revealed just how much of a deplorable Sadist he is: He took an interest on Mash and snuck into her room and tried to break her fingers just to see if she'll emote, no wonder Dr. Romani was so furious. In the end, Beryl had a completely agonizing (and satisfying) Rasputinian Death with a little help from fellow Crypter Peperoncino and Mash flat out said that no one is gonna understand his twisted meaning of love. All of those should confirm that yes, he doesn't REALLY have a sad backstory unlike what most Nasuverse antagonist had, you can hate him to your heart's content.
