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Anime and Manga
- Yu-Gi-Oh!: While many lesser villains are cheaters, the various Big Bads tend to avoid breaking the rules, since they have to defeat Yugi fairly in order to win the Millennium Puzzle from him. This doesn't stop them from exploiting various gaps in the rules, or from using Shadow magic to gain an advantage of course; Dark Marik is particularly sadistic when it comes to devising headgames to distract Yugi from the game at hand.
- Grimmjow toward Ichigo in Bleach. After killing Loly and Menoly and saving Orihime, he drags her to where Ulquiorra's left Ichigo for dead and demands she heal him so they can have a proper battle. He even turns on Ulquiorra when the latter appears and demands to know why he's having Ichigo revived. In truth, Grimmjow was doing it more for the sake of his own pride, rather than fair play. He wanted Ichigo at his best, before crushing him, to pay him back for scarring him.
- Then there's Ginjo, who deliberately placed a flaw in his own plan to give Ichigo a chance to thwart it. In his case, he did so in the opinion that allowing a small risk of failure was more fun.
- In Sword Art Online, the main villain Kayaba Akihiko traps ten thousand players in a virtual reality video game, and promises to let them out when the defeat the 100th floor boss. The game is fairly balanced, and so on, which starts to show this, but the real point comes when Kirito defeats the final boss (Kayaba, it turns out) on the 75th floor. Kayaba keeps his word and lets everyone out.
- Subverted by Heathcliff, his alter ego who has an exceptionally powerful unique skill that even people in-universe consider broken. He also is immortal after taking a certain amount of damage and explicitly cheats during his first duel with Kirito. The game may have been fair, but his place in it sure as hell wasn't.
- In The Seven Deadly Sins tournament arc hosted by two ancient demons, those who made it through their maze of death were divided into teams of two at random. When not enough passed to make an equal 16 team bracket, they just made golems of themselves to fill the open spots, instead of just killing them until the numbers fit an 8-team bracket setup.
- The modus operandi for Batman villain Two-Face, who believes that chance (specifically, a coin toss) is the only fair thing in the world, and will flip a coin to make any major decisions. How "fair" this is can become skewed, such as flipping a coin to decide whether or not he should honor an agreement when the other party already held up their end of the bargain or doing multiple coin flips for every petty little thing.
- Sometimes anti-heroine/sometimes villainess Lady Shiva is a Blood Knight martial artist who is constantly seeking a Worthy Opponent to defeat and kill her in hand-to-hand combat. During one battle against Richard Dragon, Richard had technically defeated her and was ready to deliver a killing blow when one of Shiva's minions interrupted the fight to save her life. An angry Shiva killed the minion for interfering and restarted the fight with Richard. However, this time, she won.
- On a different occasion, Lady Shiva battled against Batgirl (later revealed to be her own daughter, Cassandra Cain) and "killed" her by stopping her heart for a length of time and then reviving her. Batgirl, as a former Child Assassin that became The Atoner, was a Death Seeker just like Shiva, which is something Shiva didn't find particularly sporting, so she killed and resurrected her enemy just to give Batgirl a taste of death that would ease her guilty conscience. It worked, and Batgirl went on to win their duel.
- Marvel has Arcade, whose M.O. was trapping heroes in carnival-themed death traps and getting his kicks on seeing them try to escape. He claims that his Murderworlds are designed so that the heroes all have a chance to escape. A small chance, but a chance nonetheless.
- In the The Legend of Spyro fic The Legend of Spyro: A New Dawn, Deadlock makes sure that Spyro and Cynder have a fair chance of saving the dragon eggs she has captured to sacrifice because years ago she was denied that same chance and can't bring herself to force it on anyone else.
- In the Sakura Wars fic Price For Power, Tenkai confronts the Flower Division with an entire army of demons, though the demons are only meant to ensure that they don't escape and he intends to fight them himself because, even though he wants to destroy Tokyo, he wants to give Sakura and co. a fair chance to stop him... only to shrug off all of their attacks and wipe the floor with every single one of them.
Film — Live Action
- The vital part of Jigsaw's games is that all his victims have a chance to prove their desire to live and free themselves from his traps. This usually involves self-mutilation and/or psychological torture.
- Subverted in Saw III: Amanda's traps are designed without any actual chance of escape, which Jigsaw acknowledges as proof that Amanda is too unstable to carry on his legacy.
- Carpe Jugulum by Terry Pratchett introduces the old Count Magpyr, the traditionalist vampire who litters his castle with weapons that can be used to take him down - instructions and diagrams included! After all, taking a stake through the heart is one thing; looking like Swiss cheese because the average peasant can't find your heart is quite another. For him, this is also Pragmatic Villainy: if he can be overthrown by anybody with a lot of guts and a little luck, the villagers will generally be satisfied with 'killing' him (something a vampire can eventually recover from) rather than being so horrified that they'll take extreme measures to make sure he's Deader Than Dead.
- The Duke of Ch'in in Bridge of Birds has elaborate mazes and death traps that always give the heroes just enough of a chance to escape. Master Li eventually figures out that this is because the Duke is like a child who protects himself with things straight out of fairy tales and believes it just wouldn't be as much fun if his victims had no chance of winning.
- Luxord of the Kingdom Hearts series teleports Sora's allies away to fight him as a Duel Boss, making the battle a Timed Mission where they have to attack each other to deplete a time gauge.
- In the same series, Hades mostly tries to defeat Hercules by sticking to the tournament format of the Coliseum and pitting him against powerful opponents. The second game shows he's grown tired of this though, and during his Villainous Breakdown decides he's had enough playing by the rules and promptly cheats.
- Tomb Raider (2013): During the Co-Dragons' Extreme Melee Revenge on Lara for her murder of their brother, Mathias steps in and stops them from killing her outright.
- Akuma of Street Fighter fame is a Blood Knight who seeks someone with the raw skills to defeat him. He will openly mock any character that obtains power by artificial methods (Seth and Bison) or that utilizes weaponry (Vega and Crimson Viper). By contrast, he rejects any opponent too weak to pose a challenge.
- In Final Fantasy IV, Rubicante is a Noble Demon who heals your party before the battle, even announcing that he wants a fair fight. He does it again when the Four Fiends all come at you at once, and gives your party a final farewell before he dies.
- In Pokémon, everything is settled by a battle between trainers. Adult villains far older and stronger will concede the day to a small child once you knock out their Pokemon.
- In Jedi Knight: Jedi Academy, Jaden Korr is captured in one mission and given the chance to fight his/her way out, because the captor wants the chance to hunt a Jedi. However once Jaden starts looking like they'll genuinely escape the captor throws the rules out of the window and goes all out.
- Kusanagi (dark magical doppelganger of series protagonist Kyo) isn't evil per se (although he definitely looks the part; in his defense, Chizuru was Brainwashed and Crazy when she created him), but he's equal parts Blood Knight and Arrogant Kung-Fu Guy and is something of a crass and vulgar loudmouth. In 2002, he has a special intro against characters who fight with weapons, such as Choi, Chang, Billy, and Whip. This also doubles as a Shout-Out to a similar line delivered to Tetsuo by Kaneda, as both Kaneda and Kusanagi are voiced by Mitsuo Iwata.
Kusanagi: "Temee! Sude de shoubu shiagare!" ("You [bastard]! Fight me with your bare hands!")
- The Legend of Zelda: During the various boss fights with Ganondorf, whenever he knocks Link down after an attack, he always waits for Link to get back up before continuing the fight.
- Then there's Demise, the final boss of The Legend of Zelda: Skyward Sword. He's so fascinated and impressed that Link is not only unafraid of him, but willing to fight him directly, that he agrees to a final duel with Link before he moves on to the Triforce. He even waits for Link to get prepared and come to him.
- Senor Senior, Sr., a villain from Kim Possible, became an arch-villain not for good or evil purposes but because he's a billionaire seeking amusement. He has studied the failures of genre-blind villains and regards them as important traditions. Lampshaded in one episode, when Senor Senior, Jr. asks why they're leaving the room while a Conveyor Belt of Doom finishes off the heroes. Sr. Senior, Sr. explains that leaving the room to allow Kim a chance to escape is what a "proper villain" would do.