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Outside Man, Inside Man

 Outside Man, Inside Man
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This is a two-character dynamic that frequently shows up in fiction.
Somewhere in the Backstory, two male friends are making their way in the world as a pair of henchmen, keeping up the Masquerade for the Ancient Conspiracy, going to war for The Empire or doing hits for The Syndicate.
One day, orders come down from the top to Shoot the Dog. The "Outside" man pulls a Heel–Face Turn and refuses to go along with it. They may have fallen In Love with the Mark, had his training wear off, or decided Even Evil Has Standards.
This moral awakening will prompt him to announce that he's leaving and ask for his companion to come with him. The "Inside" man will refuse, and his reason why will be reflected in his role in the series:
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 Outside Man, Inside Man / int_1367cea0
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Worm has the relationship between Number Man and Jack Slash. Both were kept under the thumb of King, the original leader of the Slaughterhouse Nine, until they worked together to kill him. While Jack hated King he chose to rebuild the Nine so he could change the world via killing. Number Man chose to take a separate path, eventually joining Cauldron and working through them to change the world.
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Denam and Vyce, at the end of chapter 1 in Tactics Ogre. If you refuse your orders, he goes off to follow them "because it's the only way to win the war", leaving the other troops to kill you while he does so, and you fight him later. If you obey your orders (for the same reason), you become the Inside Man, and you'll have to fight Vyce later under different circumstances.
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Variation: Akira Hojo and Chiaki Asami from the manga Sanctuary deliberately embrace this trope. Their plan to remake Japanese society calls for Hojo to rise to power as a Yakuza, providing under-the-table funding and "moral support" to Asami's career as a politician. (They played Janken to decide who would be who.)
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Inverted with Sasuke and the titular character of Naruto. Sasuke abandoned Konoha to join the villainous Orochimaru while Naruto continued to serve their home village. At the end of the manga the trope is played straight when Sasuke resolves to kill the Kages to purge the system of the corruption they represent while Naruto defends them despite the problems of the villages.
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In Nikita this is the dynamic between Nikita and Michael. Nikita rebels against Division when it kills her fiance while Micheal stays loyal as Percy's Dragon. To a lesser extant this also happens between Nikita and Birkhoff. They are good friends and Nikita wants him to join her in the fight against Division but Birkhoff is too scared of Percy. In season two they both join her, though Nikita's pupil Alex then takes over this dynamic.
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Inversion: Knives and Vash, Trigun The 'organization' in this scenario is the human race and Knives evidently honestly believes himself to be the good guy. He puts together a more typical evil organization later on.
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In Tales of Vesperia Yuri used to serve as Imperial Knight alongside his friend Flynn, but left after events, described in The First Strike. As a result, he sees Knights as an inept organisation, that serves as nothing more than a tool for corrupt elites, while Flynn tries to fix the problem from within. Ultimately, Flynn manages to reach the position of the Commander, and starts to change the Knights for the better, but not before Yuri has to murder several high-ranked criminals, who would have avoided justice otherwise.
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Spike and Vicious in Cowboy Bebop were originally both low level enforcers for the Red Dragon Syndicate. At some point after falling in love with Julia, Spike decided to leave the organization only for Vicious to find out and try to kill him. Since then Spike has wandered the solar system as a bounty hunter while Vicious rose through the ranks of the Syndicate, eventually launching a coup to take control.
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 Outside Man, Inside Man / int_49a88435
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Outside Man, Inside Man
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Judges Drace and Gabranth in Final Fantasy XII. Not played straight though, as Gabranth only stays the inside man because Drace urges him to after her attempt to become an outside man ends in tragedy.
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 Outside Man, Inside Man / int_4fc1c922
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Outside Man, Inside Man
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In Wicked, Galinda and Elphaba become this trope. They become good friends at school, but after they see the Wizard, Elphaba decides to work against him, and Galinda decides to work for him. At the end, they forgive each other and (sort of) reconcile their friendship before Elphaba has to fake her death and leave Oz forever. (In the book, she actually dies, and doesn't see Glinda so soon before it either, and the emotions are much murkier, less clear, and more mixed with bitterness on all sides.)
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Right-Eye and Redcloak, from the Order of the Stick prequel book "Start of Darkness". Right-Eye leaves after deciding their leader Xykon is too dangerous to continue serving, while Redcloak believes he's already invested too much in The Plan to quit now.
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 Outside Man, Inside Man / int_57ad0c07
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Wesker and Birkin in Resident Evil, though they remained friends and comrades. A slight variation on the usual trope since Wesker is, if anything, the more evil of the two, and his reasons for leaving Umbrella were entirely selfish and not based on any moral objections to the company's actions. Still, the scene where Wesker tries to convince Birkin to leave Umbrella plays a lot like this trope.
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In a Good Cause— starts its main narrative on Earth, at the tail end of a discussion that has turned the old friends Richard Altmayer and Geoffrey Stock into this, with Stock willing to set his Federalistnote in the context of the story, Federalists are people who believe that humanity should unite into a single federation ideals aside and obey the draft for the war against the fellow human world of Santanni, while Altmayer refuses to fight against fellow humans. Stock then spends the rest of the story gradually rising in Earth's government in every timeskip, while Altmayer keeps getting himself arrested for various (attempted) stunts. The end of the story reveals Stock never actually gave up on Federalism, and has been working for years within, and later at the head of, Earth's government to set up the right situation for the establishment of a United Worlds of humanity.
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 Outside Man, Inside Man / int_68959735
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Somewhat inverted in Suikoden II, where both the main characters essentially start out as outside men, with one slowly working their way into the system to subvert it from within. The trope follows from there, though, as there are multiple points where the outside man begs the inside man to leave the evil empire, the inside man eventually overthrows the original leader and becomes the one in charge, and the entire scenario ends with a Redemption Equals Death outcome. Well, unless you get the best ending, anyway.
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D&D 4th edition used this trope for their alignment system. Good characters are willing to overthrow corrupt governments, while Lawful Good characters prefer to change things from within.
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Pulp Fiction: the impetus for the change here is not the job itself, but the fact that the two guys escape being repeatedly shot at at near range. Jules, the outside man, takes this as a miracle and repents, deciding to give up the business and Walk the Earth. Vincent stays in, and is later killed by Butch. Since the film is in Anachronic Order, the moment of Jules' decision is treated as the finale though the "miracle" is at the beginning, and Vincent is killed in between.
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Mello and Near in Death Note were both proteges of L. After his death they set out to avenge him by taking down Kira. While Near followed the same approach of allying with law enforcement as L, Mello followed a more vigilante route.
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On Lost, Jacob and Smoke-Monster play out something like this after Smokey discovers the woman that raised them had actually killed their real mother
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Adora and Catra in She-Ra and the Princesses of Power, respectively. Catra is a pretty textbook Type 2, knowing full well the Horde is using them but wanting to use it right back to gain more power for herself. She succeeds at the end of season 1, supplanting Shadow-Weaver as The Dragon to Lord Hordak.
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The Secular Missionary arrives in Fallen London asking the player's help finding her husband, the Revolutionary Firebrand. The two of them were searching for the Cave of the Nadir together - a chamber beneath the Fifth City that glows with the colour of forgetfulness, full of lost archaeological secrets - but turned on each other after he learned she intends to sell it to the highest bidder rather than use it as the revolutionaries' ultimate secret base. Unfortunately, neither of them trust each other any more, but only he knows where to find it and only she has figured out how to get in.
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Basically the whole plot in The Magnificent Kevin comic books, with Kevin just being too damn scared to leave.
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Most movies that feature this are probably looking back to Logan's Run. Interestingly, in the book the inside man was secretly running La Résistance, which was why he couldn't afford to go AWOL. In the movie he just flips out and eventually gets dead.
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