Deception, trickery, thievery, and manipulation are often seen as the tools of criminals and ne'er-do-wells, often with good reason. But sometimes, a character skilled in skullduggery chooses to use his talents for the good of others, whether by undermining criminal enterprises from within or going after bad guys directly. Villains and criminals tend to be caught off guard by the Underhanded Hero, as most do-gooders take the more direct approach when confronting evil and would never degrade themselves with such underhanded methods.
A heroic thief or assassin is by definition a Underhanded Hero, but the inverse is not always true. To qualify as an Underhanded Hero, a heroic character needs to be skilled in a combination of thievery, stealth, deception, acrobatics and manipulation.
The Underhanded Hero fulfills a particular fantasy in the minds of audiences. Where the Power Fantasy plays into an audience's desire to see the hero succeed through force, the Underhanded Hero plays to the Underdog Fantasy, in which the hero succeeds in spite of the odds being stacked against him. By being smart, cunning, and crafty and by avoiding danger rather than facing it head on, the Underhanded Hero can take down foes that out-muscle, out-number, or out-gun them by orders of magnitude.
Compare to Shoot the Dog
For characters who use rogue-like skills in defense of king and country, try Spy Fiction.
- The Caped Crusader is the archetypal powerless superhero, and as such, his fighting style relies heavily on misdirection and agility. His other skills include stealth, spying, and hacking, all done in the name of protecting Gotham City.
- The rest of the Bat Family also fit this trope, even wheelchair-bound Oracle.
- In Runaways, Chase Stein's major value to the team is that he's willing to do things that his teammates will not in order to advance the team's goals, like hounding the members of the New Pride to make sure they never reconvene, or making deals with criminals like Pusher-Man and Maneater to acquire things that his team needs but cannot obtain legally.
- Many of the X-Men fit the trope being outlaw heroes. But in particular:
- Gambit was a thief before joining the X-Men. He is incredibly acrobatic and makes extensive use of his Cajun charm.
- Nightcrawler was a circus performer and fashions himself after Errol Flynn, who famously played Robin Hood. In X2: X-Men United, while being mind-controlled, he took out an entire Secret Service squad using nothing but acrobatics, short-ranged teleportation, and healthy dose of misdirection. And he came within a hair's breadth of killing the President.
- The Punisher, in as much as Frank Castle can be considered a "hero". He avoids a fair fight as much as possible, and when an outright armed assault won't work out, he'll blackmail, extort, manipulate, and intimidate his way to his objective.
"When you're on your own behind enemy lines no artillery, no air strikes, no hope of an evac you don't fight dirty. You do things that make dirty look good."
- Wonder Woman:
- Steve Trevor will lie, cheat, steal, flirt and do whatever he needs to ingratiate himself with opponent in order to get an upper hand and learn more about their operations. He's also much more likely to kill an opponent than his more famous girlfriend.
- Wonder Woman (1942): After her HeelFace Turn Paula von Gunther will lie and pretend to still be a villain in order to get close enough to those endangering her new friends to kill them.
Film - Animated
- Shrek 2: Puss in Boots. He is a stealthy and cunning swordsman, who uses his size to his advantage in a fight, and who is more than willing to use his adorable appearance to throw his opponents off guard.
Film - Live Action
- Marvel Cinematic Universe:
Scott Lang: My days of breaking into places and stealing shit are over. What do you want me to do?
- The Avengers (2012): Black Widow fits this trope to a tee. She's an assassin trained by Leviathan, the Russian equivalent of HYDRA, before eventually turning on her comrades and joining SHIELD.
- Ant-Man: Scott Lang is a former burglar, fresh out of prison. He's trying to turn over a new leaf and leave his old life behind, but the skills he perfected as a thief are exactly what Hank Pym, the original Ant-Man, needs to stop a powerful villain.
Hank Pym: I want you to break into a place and steal some shit.
Scott Lang: ...Makes sense.
- Robin Hood: A thief who steals from greedy nobles who outright steal from their citizens or tax them into oblivion. In virtually every incarnation of the character, he does so to get that money back from nobles and give it back to who it truly belongs to.
- The Hobbit: In order to prevent a useless war between potential allies, Bilbo steals the Arkenstone, the crowning jewel of the treasure that the Dwarves seek to reclaim the first place, and hands it over to the Elves so they can bargain for a ceasefire and force Thorin to fullfill his obligations to the Men of Dale.
- Michael Vey: In their efforts to save the world from the villainous Dr. Hatch, the Electroclan has resorted to tactics such as manipulation, blackmail, and threats, which are preferred tactics of Hatch himself. However, they only do these things when necessary, and on a much smaller scale than Hatch does. (It's also worth noting that most of the people that they do this to are working for Hatch.)
- Mistborn: The Original Trilogy: The plot to overthrow the Evil Overlord is basically a combination heist/scam by a talented elite theiving crew with the army only intended to be backup.
- Redwall: Characters' morality is pretty much determined by their species, so while heroic species like otters and mice can be thieves and pirates, they only target vermin.
- The Saint. Simon Templar is a Con Man who has repeatedly taken out criminals by kidnapping them, tricking them into killing each other and even performing Vigilante Executions.
- John Rumford in Victoria doesn't steal much, but certainly practices stealth and manipulation. As an ex-military specialist in irregular warfare, he finds that his subversive skills are of excellent use both on and off the battlefield when tackling the corrupt state government and the organized crime cartels it protects.
- Samuel Vimes of Discworld may be an utterly dedicated guardian of the law and citizenry of Ankh Morpork, but that doesn't mean he fights fair. Physically or mentally. The "Vimes Elbow" is apparently something of a minor legend in the underworld, and he can scheme with the best of them (examples of his cunning across the series would probably fill half the page). He's also, by his own admission, a "professional suspicious bastard", and outright expects villainy until proven otherwise.
- Burn Notice: Michael Westin is a burned spy, dumped in Miami after the CIA disavows him. To make ends meet, he uses the skills he picked up as a spy to deal with bad guys and help the innocent people said bad guys target. This usually involves actually infiltrating said group of bad guys, and running some sort of scam or con that causes them to overextend and get in trouble, mostly with other rival criminal organizations who then wipe out the trouble making group (or both wipe each other out). While Team Westin very rarely directly kills, they have absolutely no problem putting bad people in a position to die easy.
- Game of Thrones: The Faceless Men may qualify, as they seek out evil men to kill at the discretion of their patron, the Many-faced God.
- Marvel Netflix: Daredevil and Jessica Jones both fit this trope.
- Daredevil uses his supersenses to catch bad guys unawares, often taking them out before they even know he is there, and when he does have to engage in direct combat, he makes sure his opponents are at a disadvantage, by taking out the lights or fighting in hallways.
- Despite her incredible strength, Jessica Jones rarely uses her powers in showy ways, preferring to use disguises and deception. And when she does use her strength, it is usually in subtle, creative ways. For example, she pulled apart a padlock instead of the door it held shut, and later, she leapt over an entire battalion of police officers and bent a gate shut to prevent them from following her, rather than engage them in combat.
- On Person of Interest, Finch and Reese operates in this way to save the Numbers (people about to be murdered). Reese is a Combat Pragmatist who likes to shoot bad guys in the knees and regularly assumes fake identities in order to get close to a Number. Finch is a computer genius and hacker who will as a matter of course hack the Number's cellphone and generally invade his/her privacy in order to figure out the source of the threat. They are later joined by the sociopathic Shaw and former Psycho for Hire Root who employ even more questionable methods in order to stop the bad guys.
- Stargate SG-1: Vala Mal Doran, after joining the SGC. A reformed con artist, she uses her knowledge of the galactic criminal underworld to help protect Earth and the galaxy at large. Her piece de resistance is perhaps when she wipes her own memory, in order to give the rest of the team a chance at capturing her daughter Adria, the Crystal Dragon Jesus Big Bad of Season 10.
- Dungeons & Dragons: The rogue class falls into this trope, provided said rogue is being played as a hero.
- In D&D 3.5, rogues are skilled in such things as: Bluff, Forgery, Intimidate, Open Lock, and Sleight of Hand, not skills an honorable hero tends to spend a lot of time practicing. They also possess the Sneak Attack ability, which allows the rogue to do extra damage is they can catch their opponents unawares or at a disadvantage.
- In later editions of D&D, many of these skills are rolled into another broader skill, Thievery.
- The 3E Book of Exalted Deeds introduces the Slayer of Domiel Prestige Class, essentially a good-aligned version of the Assassin and intended for use by Rogues.
- The 3.5 book "Complete Adventurer" had a pair of prestige classes called the Shadowbane Inquisitor and Shadowbane Stalker, both of which require the ability to Sneak Attack and the ability to cast Detect Evil in order to join. This means that players wishing to join must take levels in Rogue and Paladin, the latter of which requires the character to be Lawful Good.
- Starfinder has the Envoy class, which is meant to play like a roguish space captain. Armed with nothing more than basic pistols and blades, the Envoy's sharp tongue and tactical skill can stand toe-to-toe with the Technomancer's magic, the Soldier's weapons, and the Mechanic's tech.
- There's also the Operative class, which plays very much like the rogue/thieves of other systems. They are the only class (besides Soldiers) with proficiency in sniper weapons, and when in close-range combat, they can use their Trick Attack to deal extra damage.
- Assassin's Creed: The titular assassins only slay those who have committed grave crimes against their fellow man.
- City of Heroes: Later in the game's run, all ten archetypes were opened up to both heroes and villains, allowing players to run a Heroic Stalker. All Stalkers started the game with a low-level stealth power. Their offensive power sets were fast, melee attacks, and their defensive power sets were usually agility-based, focusing on dodging damage, rather than tanking or healing it.
- Dishonored: Player character Corvo Attano is framed for the murder of the Empress of the Isles and the disappearance of Princess Emily. He fights to save the princess and clear his name, using his natural stealth and a cadre of supernatural powers, most of which are themed around stealth and nondetection.
- Mass Effect: Kasumi Goto. While she is a thief, every instance of her has her using her skills for the greater good, from protecting the Alliance by recovering her greybox to a casino heist to benefit children.
- Sly Cooper: The titular raccoon only uses his thieving skills to take on bad guys, as there's no honor in taking from honest folk.
- Styx: Master of Shadows: The goblin thief Styx starts the game trying to steal the Heart of the World Tree, one of his world's greatest treasures. By mid-game, however, after been offered enough coin and Amber to care, he starts using his skills as a thief to bring down the corrupt humans who are trying to start a war between men and elves.
- Garrett from the Thief series doesn't like playing hero, but as the games repeatedly force him into that role he is able to use his legendary prowess in stealth and infiltration to take down bad guys who severely outclass him in the raw power department.
Garrett: I've never robbed a god before. It'll be a challenge.
- The Order of the Stick: Haley Starshine, the party's rogue. She's stealthy, greedy, and crafty, but she once she realized the fate of the world was at stake, she decided to turn her efforts to saving it. Probably her best moment was convincing a raging flesh golem to turn on its creator using nothing but the truth, then tricking it into walking into an active volcano.
- Teenage Mutant Ninja Turtles
(After taking Leo by surprise and tripping him)Splinter: Was that fair?Leo: No!Splinter: Did I win?Leo: [Beat] I see your point.Splinter: Seek victory. Not fairness.
- The titular turtles stick to the shadows as much as possible and are not above fighting dirty.
- Teenage Mutant Ninja Turtles (2012): This version of Master Splinter has specifically taught his sons that, since you can lose a fair fight, it is best not to fight fair.