Fair Play Villain

A Fair Play Villain is a villain who, when the hero is at their mercy, gives the hero a Hope Spot. If the villain traps the hero in their prison, they'll allow them an escape chance. If they get the hero into their deadly arena, they promise to let them go if the hero can beat the monster. This type of villain suffers from Bond Villain Stupidity -- he could just kill the hero now, but where's the sport in that?

The defining characteristic of the Fair Play Villain is that this act is sincere. He's not lying or deceiving the hero, he's genuinely giving them a chance to win, and will probably (though not always) hold up his end of the bargain if they prevail. He might hope the hero fails, or bend the rules a bit, but ultimately he still gives the hero the opportunity to beat him.

The villain's interest may be in proving to the hero how helpless they are by kicking them while they're down, giving them a second chance so they can fail again. Perhaps the villain is interested in what the hero's capabilities are, or wants to see him prove himself. The villain may be Nigh Invulnerable and believes Victory Is Boring, and finds more challenge in giving the hero a fair shot. The villain may be an Anti Villain who wishes to best the hero in a fair contest.

Compare Why Don't Ya Just Shoot Him, the logical question that this trope answers. May overlap with Let's Fight Like Gentlemen, Just Toying With Them, Hunting the Most Dangerous Game, and Mercy Lead. See also the Spirited Competitor and Worthy Opponent. Can be related to the Sadistic Choice.

Has absolutely nothing to do with Jonny Fairplay from Survivor.

Anime

 * Yu-Gi-Oh, this is standard operation for most villains, since conflicts are almost universally settled by a duel. Particularly notable is Marik, who will lure Yugi into a Death Trap then allow him to duel for his freedom.
 * Grimmjow toward Ichigo in Bleach. After  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

Film -- Live Action

 * In Saw, 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.

Literature

 * Carpe Jugulum by Terry Pratchett, the traditionalist vampire who litters his castle with weapons that can be used to take him down - instructions included! It's also a clever survival tactic, since the would-be hunters aren't pressured to find more permanent ways to kill him.
 * 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.

Comics

 * 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. Of course, 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.

Video Games
"Kusanagi: "Temee! Sude de shoubu shiagare!" ("You [bastard]! Fight me with your bare hands!")"
 * 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.
 * 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 battle.
 * In Pokémon, everything is settled by a battle between trainers. (This also applies to the TV show.)
 * In Jedi Knight: Jedi Academy, Jaden Korr is captured in one mission and given the chance to fight his way out. As Jedi are perfectly capable of combat even without a lightsaber, it doesn't end well for his captor.
 * 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 It Good. 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.

Western Animation

 * In Kim Possible, Senior Senior, Sr., Lampshades this. When Senior Senior, Jr., asks Why Don't Ya Just Shoot Him, he explains that leaving the room to allow Kim a chance to escape is what a "proper villain" would do.