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This is a quick wick check of Outside Man, Inside Man. As the trope has under 50 wicks, every one of them will be checked.

    Correct - 5 of 24 (20.8%) 
  1. Civil War: The Marvel Civil War, with heroes supporting a Super Registration Act fighting those who refused to reveal their identities. Intended to be an Outside Man, Inside Man situation, with the pro-reg group trying to head off an even worse situation by co-operating. This also went meta, the resulting Fandom War, pitting the authors of said story arc versus most of the rest of the fandom and their fellow writers.
  2. Snow White and Seven Dwarfs:
    • Outside Man, Inside Man: Outside Man to Ken's Inside Man. A very understanding version, though: Fujimaru knows Ken well enough to not bother with asking him to defect with him and he doesn't hesitate to trust the man with his life, regardless. - some context issues, but I'm confident this is an actual example.
    • Snow White and Seven Dwarfs: Outside Man, Inside Man: The Inside Man to Fujimaru's Outside Man. As noted in Fujimaru's section, they have a much less conflicted version of this: while Ken briefly tries to convince Fujimaru to rejoin the government, it's clear that Ken would never do anything to harm Fujimaru, technically enemies or not. - needs some rewriting, but again, seems like an actual example.
  3. Wings of Fire: Outside Man, Inside Man: In The Lost Continent, the protagonist and his friends end up getting involved in a revolution aiming to overthrow the HiveWings. Blue then encounters his father, Admiral, who is happy with his life being farmed for silk because it puts him in the position to petition the queen for reforms. After seeing how comically little Admiral still managed to accomplish despite decades of work, Blue decides to oppose him and still try to escape and fight back, but Admiral is terrified that Blue's actions will undo everything Admiral has done and get the HiveWings to put them back in chains like it was when Admiral first arrived.
  4. The Last of Us (2023) S1 EP7: "Left Behind": Outside Man, Inside Man: Set up with Ellie and Riley, with both growing up in the same FEDRA military school for orphans, Riley choosing to join the fireflies and Ellie refusing, but instead subverted when Riley ends up infected.
  5. Loki (2021): Outside Man, Inside Man: Loki ("outside man") and Mobius's ("inside man") dynamic in the show follows this pattern. They work for the TVA and find the hiding spot of the Cop Killer together, Loki follows her through the portal while Mobius is left behind, Loki discovers that she was Good All Along and falls in love with her, both of them are captured, Mobius doesn't belive Loki and has him tortured, interrogated and left to be "pruned". Then Mobius finally discovers the truth and the two form an alliance only for both of them to get "pruned".

    Zero Context - 9 of 24 (37.5%) 
  1. Code Geass: Outside Man, Inside Man:
    • Lelouch and Suzaku, although Lelouch had already "left" the empire before Suzaku joined it, and they became friends in the interim. It works more if you look at it from Suzaku's point of view after the events of the first season. - Probably still an example despite all the weasel words.
    • Rakshata and Lloyd might also be an example, considering how they used to work together and Lloyd likely never worked for anyone other than the empire. - Seems speculative
  2. Lessa:
    • Outside Man, Inside Man: She befriended Mindy-Mindy during their time together, and tries to convince her to join her in Season 2. It works, although Mindy-Mindy soon pays the price for her redemption. - I suspect this is misuse, but there's not enough information to know for sure.
    • Lessa: Outside Man, Inside Man: The Inside Man to Lucy's Outside Man. - Completely zero context
  3. The Spectrum Game: Outside Man, Inside Man: The Inside to Iago's Outside, being an Internal Reformist who seeks to change Apex from the inside, while Iago would prefer to destroy the organisation outright. - doesn't establish that Iago was previously a member of Apex (assuming he was. This is misuse if he wasn't)
  4. Civil War (2006): Outside Man, Inside Man: Captain America was Outside, Iron Man was Inside. - Based on other information, I'm reasonably confident that this example would be correct if expanded.
  5. Arc of a Scythe: Outside Man, Inside Man: Rowan is the outside man and Citra is the inside woman to the Scythedom in Thunderhead.
    • Could be taken further, as Greyson is also an Outside Man, possible even further outside than Rowan by virtue of having no insight into the Scythedom's politics or proceedings. - Even outside of the bad example indentation, I suspect this is misuse
  6. Gungrave: Outside Man, Inside Man: Harry and Brandon.
  7. Tactics Ogre: Outside Man, Inside Man: With Denam and Vyce. Your choice at the end of Chapter 1 determines who is the inside and who is the outside man.
  8. Tales of Vesperia: Outside Man, Inside Man: Yuri and Flynn, respectively.
  9. Arkn: Legacy: Outside Man, Inside Man: Timothée is the Outside Man to Malistrade's Inside Man after leaving the Society of the Purple Rose. - doesn't mention a personal connection between the two characters

    Misuse - 2 of 24 (8.3%) 
  1. Rune Factory 5: Outside Man, Inside Man: As an established member of SEED before the game starts, Scarlett is the inside man to the protagonist's outside man.
  2. Tropes H To Y: Outside Man, Inside Man: This is how the Nintendo Direct describes the two different paths. The Hoshido path is fighting the enemy from the outside, while the Nohr path has you fight important leaders and change Nohr as a member of the "evil" team.

    See Also and Indexes - 8 of 24 (33.3%) 
  1. Cop/Criminal Family: "May overlap with"
  2. Inside Job: "generally unrelated to"
  3. Institutional Allegiance Concealment: Link seems slightly misleading.
  4. Internal Reformist: "Compare"
  5. Red Oni, Blue Oni: "Compare"
  6. Stock Characters: Index
  7. Laconic.Outside Man Inside Man: Can safely be ignored
  8. TV Tropes Superhero Team

Analysis of on-page examples:

    Correct - 9 of 34 (26.5%) 
  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.)
  7. 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.
  8. 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.
  9. 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.

    Missing the "moral awakening" - 5 of 34 (14.7%) 
  1. 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.
  2. Fushimi and Yata from ''K" are a semi-example, since neither side is good or bad, and neither side is the protagonist, either. Still, their relationship in the story revolves around how Yata feels betrayed that Fushimi left HOMRA and joined Scepter 4.
  3. 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  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.
  4. 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.
  5. 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.

    Completely misuse - 6 of 34 (17.6%) 
  1. 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. -
  2. 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.)
  3. The Man-Kzin Wars books have two major characters who seem to fit this trope. Claude, Harold, and Ingrid are three friends in a love triangle who join the planetary defense force just before invading Cat-Like Aliens ultimately succeed at conquering their human colony and holding it for a generation. Claude and Harold get left behind by Ingrid during the confusion of the military evacuation; when Ingrid comes back decades later (and still young thanks to time-dilation) as part of a covert operation, she needs to tap them as contacts but both Claude and Harold have long ago abandoned active resistance: Claude has chosen to cooperate with the occupation forces and became their chief of police in the Capitol, while Harold started a nightclub there and became a big player in the criminal underworld. Naturally, they've fallen out with each other to the point of practically being nemeses. Both of them originally sought their positions in the belief that they could 'do good' through them, but by now have become largely corrupt. Both of them are also still very angry at Ingrid for abandoning them, but both of them are tempted by the possibility of regaining their integrity and throwing off their alien masters—who are all too happy to kill and eat suspected 'feral' humans. The resolution is quite tumultuous.
  4. Nicholas Easter and Marlee in the John Grisham legal thriller The Runaway Jury as well as in the movie version. Nicholas got himself planted as a jury member to influence a court decision involving large corporations (in the book it was a tobacco company and in the film it was the firearms industry). Marlee was on the outside interacting with lawyers on both sides of the case. Their motivations and MO differ in the two media.
  5. 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.
  6. 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.

    Zero Context - 14 of 34 (41.2%) 
  1. Basically the whole plot in The Magnificent Kevin comic books, with Kevin just being too damn scared to leave.
  2. Civil War (2006) was this on a large scale, with Captain America leading the Outside faction while Iron Man headed up the Inside. Officially, the pro-regs are Type 3 - trying to blunt Superhuman Registration from within - but there's a lot of Depending on the Writer and Alternate Character Interpretation here.
  3. Repo Men, although given the All Just a Dream Reveal, it's a little hard to reduce to this.
  4. 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.
  5. Train and Creed, Black Cat.
  6. Gaula and Gulen in Kishin Douji Zenki.
  7. 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
  8. Cecil and Kain in Final Fantasy IV.
  9. Celes and Kefka, Final Fantasy VI
  10. Final Fantasy VII:
    • Zack and Sephiroth.
    • Also Angeal and Zack in Crisis Core.
  11. 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. - probably misuse, but not enough context to tell
  12. Tommy and Sam in Mafia: The City of Lost Heaven game (outside and inside, respectively).
  13. Brandon Heat and Harry MacDowell from Gungrave.
  14. 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. - I know enough about the work to know this is an example, but it needs some work.

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