Circling Monologue

While a foe is Monologuing, they'll be circling the hero like a wolf circles a lamb, hoping to ensnare the hero with their arguments and offers like a python hugs its victims. Spiraling ever inwards as their seductive yet Creepy Monotone reaches deeper and deeper to the core of the hero's motivation. The hero will usually have the facial expression of a deer in the headlights of an eighteen wheeler, or seem deeply conflicted, confused, or about to have a nervous breakdown. This is made all the creepier when the hero is bound and can't turn to face the villain, as they go behind the hero, trivializing how easily they could backstab the hero and kill them, or will if it's a Just Between You and Me moment.

It's rare, but sometimes the hero will do this. In this case, the hero usually isn't the ideological predator, but a flexible thinker, offering a Last Second Chance while The Stoic Evil Overlord remains dead set in their ways, immovable and proud before their impending fall. Some examples are both of these at once, where the hero and villain circle each other while trying to convert each other.

Often a source of Foe Yay.

Anime

 * In the very first episode of the animated adaption of Fate Zero, both Tohsaka Tokiomi and Kotomine Risei circle Kirei while they explain their Xanatos Gambit to him in an effort to convince him to join them. See here for an example.

Films
"Syndrome: You sly dog, you had me monologuing!"
 * Grendel's mother in the 2007 movie of Beowulf does this to the eponymous hero. She promises the trifecta of Sex, Money, and Power, strumming every chord of this flawed hero's heart and pride as she circled him. Too bad the original version is a much more straightforward, violent, bloody and gory physical battle. (They Changed It, Now It Sucks, say some.)
 * In Star Wars: Revenge of the Sith there's an example of a heroic, well, Anti-heroic circle. Anakin rounds Palpatine as the latter calmly and matter-of-factly lays out his motivations and plans, doing his best to convince Anakin that it's best for Padme.
 * The same happens between Anakin and Obi-Wan before their fight on Mustafar. And, in Attack of the Clones, Count Dooku was circling and tempting a captive Obi-Wan. The Star Wars prequels love this.
 * Done in the Dungeons & Dragons movie.
 * The climax of Big Fat Liar.
 * Scar does this to Simba on The Lion King as he confronts him for being responsible for Mufasa's death.
 * Earlier, the hyenas briefly surround Simba, Nala, and Zazu.
 * Also done in The Lion King II, in an odd example, Zira is talking to Simba, but circling Kovu.
 * Adria when talking to Vala in The Ark of Truth.
 * Wormtongue does this to Eowyn in The Two Towers, during his "Who knows what you've spoken to the darkness..." speech.
 * When the titular Corpse Bride finally confronts her murderer.
 * In The Princess and The Frog, Dr. Facilier does this to  This scene also doubles as Fetish Fuel.
 * The Prince of Egypt has this where Rameses' two priests circle Moses during their Villain Song
 * In the climax of Labyrinth, Jareth circles Sarah in this manner as he explains how, while he is capable of cruelty, he has been "generous" to her all along. Her response is the heroine's speech from the play that inspired her adventure in the first place, and a battle of wills ensues.
 * Jim does the heroic version in Treasure Planet, but it's mainly to tell Silver that he won't be fooled a second time, condemning him for what Jim thought was a bastardly speech, and letting him know that he won't let Silver ever get ahold of the treasure which serves as both characters' motivation.
 * Frollo in the Disney version of The Hunchback of Notre Dame offers
 * This is Mother Gothel's favorite choreography in Tangled. She circles Rapunzel semi-affectionately at the start of her Villain Song, "Mother Knows Best." However, in the reprise of this song, she takes it Up to Eleven, not only circling Rapunzel affectionately, but with mockery, derision, and she even does a semi-circle that has a seductive twist. Just watch for yourself.
 * Rock a Doodle has the scene where the evil owl and his henchowls are shown threatening the farm animals as the barn starts to fill up with water by singing "No Batteries!" (which for some reason contained the lyrics "Twiddly-dee, twiddly-dee") while marching around them in a circle.
 * The Singing Cat Gang actually do this to Tom and Jerry during the Big Lipped Alligator Moment from Tom and Jerry The Movie.
 * Parodied in Cloudy With a Chance of Meatballs: The mayor is trying to convince Flint to make more food fall from the sky, and uses Offscreen Teleportation to great and hilarious effect. First he whispers in one ear, then the other, then somehow from above. While driving a Rascal scooter.
 * Syndrome starts this when confronting Mr. Incredible after the Time Skip, but is interrupted by a thrown tree trunk to the face.


 * In The Dark Knight Saga at a party scene The Joker circles around Rachel and appears to sniff her while calling her "beautiful."
 * In The Matrix Reloaded, this trope is subverted, Agent Smith clones surround Neo and each one of them speaks part of the monologue while the camera pans around giving the impression he's circling Neo, when in fact the clones are mostly just standing still or walking towards Neo.


 * Teatime does this to Susan in the movie version of Hogfather.

Literature

 * Harry and Voldemort's final battle in Harry Potter and The Deathly Hallows starts with them circling each other, debating who will triumph. Harry is level-headed, assured that he has the upper hand, while Voldemort is arrogant and dismissive, refusing to believe he can be beaten.
 * In Who's Afraid of Beowulf? by Tom Holt, the last viking king, Hrolf Earthstar circles the evil Sorcerer King before battle, determined to break his attempt to rule the world. Unusually, the mighty but doomed villain accepts the Last Second Chance given by the hero. After all, someone could have got killed.
 * This happens at least twice in Madeleine L Engle's books -- A Wind in The Door and Many Waters, to be precise (although this is more of forcible-possession than monologuing, in both cases). In the latter, it's called the Circle of Extinction, giving this trope its former name.
 * A hero-to-villain example occurs in The Vor Game. Magnificent Bitch Cavilo is in a suit of Power Armor that has been depowered and acts as a Tailor-Made Prison, leaving only her head able to move. As Miles and Gregor pressure her for information, Miles repeatedly paces behind her because he can see it makes her nervous.

Live Action TV

 * In Dallas, episode "The Family Ewing" (first of the "Dream Season"), Sue Ellen comes home the night Bobby Ewing, having been out all day with Dusty Farlow. Her chipper attitude was all J.R., who was openly (as much as a proud Texan man could) mourning the death of Bobby, could take. He circles her, berating her for not (never) being there, before driving her off.
 * Doctor Who has had this, particularily with the Doctor and The Master. In Survival, the part-cheetah Master stalks around the Doctor. The scene at the beginning of part two of The End of Time has even more stalking, but it's the Doctor doing the pleading.
 * The new series Doctor Who episode "Dalek" had something like this, but with the Doctor (good guy) circling the titular Dalek instead of the other way around.
 * A strange case as
 * Buffy the Vampire Slayer has an excellent example in the first episode of the seventh season when the Big Bad delivers a Hannibal Lecture to Spike while circling him... and while shifting forms between the Big Bad of each earlier season and, at the end, Buffy herself.
 * A different use of circling than usual, but Dr Cox from Scrubs has a tendency to circle people during his rants. In one memorable scene he and J.D. actually take turns on who is playing what role.
 * In Babylon 5, in the climatic three-way showdown between Vorlons, Shadows and the Army of Light each one of the former two pick a general of the Army and try to reason him/her into following them. Shadows do this with Delenn by having impersonations of her friends and even of herself circle around her while setting forth the Shadows' doctrines. Meanwhile, the Vorlon representative manifests as a woman frozen inside a block of ice, and Sheridan circles her while she argues the Vorlon point of view.
 * In a Season Three episode of Alias, Mc Kenas Cole pulls this on Sark. However, Sark makes it a point to keep shifting so Cole is never given the opportunity to stab him in the back.

Video Games

 * Mass Effect has both Shepard and Saren trying to convert one another to the other's side at the end of the Virmire mission.
 * And again, at the very end.
 * The second instance can be a
 * But it doesn't stop Sovereign from doing just that for the final boss battle.
 * The main character can try to convince the villain to abandon his plan in Arcanum. At the same time, the villain will be trying to convince the main character of joining him to destroy the world.
 * The Fallout games love this trope, allowing the protagonist to use this on several enemies and even sometimes on the Big Bad. And at times succeed.
 * Ditto in Planescape Torment.
 * Done in Neverwinter Nights 2 both with The Dragon and the Big Bad. The verbal duel with the Dragon is important both for plot and gameplay reasons. (Basically it's a CMOA of the developers.)
 * Used by a race of Scary Dogmatic Aliens in Homeworld. With a spaceship. Circling another spaceship.
 * Used in Batman Arkham City during the battle with

Western Animation

 * The Teen Titans do this to Terra after she betrays them for the last time. Not to give her another chance, but to clarify that they will not be giving her any more chances.
 * Played with in Avatar: The Last Airbender, as Ozai circles Zuko while extolling his accomplishments in Ba Sing Se. Zuko still seems very nervous to be there, especially when he finds out that

Web Comics

 * This Sinfest comic.
 * And this Order of the Stick comic.