So, the villain has taken a hostage, and to make sure the hero understands that this is serious, the villain is holding the hostage off a roof, or over some other height. Usually, in this case, the villain just has one simple, quick request: they want the code, or the MacGuffin, or the hero's surrender. The hero gives in to the demand. And then says something along the lines of "Now let him/her go!".
Poor choice of words, it turns out, because just this once, the villain is going to comply. Immediately and literally. They let go, and the hostage goes plummeting towards whatever they were being held over.
This happens so reliably that asking a villain to let a dangling hostage go, without being very specific, probably qualifies you as Genre Blind. Even so, this trope is almost always played completely straight. We can only conclude that the sight of a hostage held in the air is the hero's cue to grab the Idiot Ball. Typically, the hostage will survive, but it may require a very well timed Big Damn Heroes moment, or just plain luck.
Variations can occur, as particularly cunning villains may find other, less obvious ways to turn a demand that a hostage be released into a request to kill them. Antiheroes have their own special variation, where they hold a bad guy over a ledge to get information, and then, when the bad guy demands he be let go... well, you know the rest. Sometimes someone's plea to let them go starts at a survivable drop and quickly turns negatory once they get higher up.
This can be a type of Literal Cliffhanger. For pretty much the exact opposite trope, see Take My Hand. The extremely literal version of a villain complying with You Said You Would Let Them Go. And the extremely literal version of this would be An Arm and a Leg.
See Also: High-Altitude Interrogation
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Done by Creed in the Black Cat manga. When Chronos came to destroy the Apostles of the Stars and rescue Rinslet, Creed took her hostage and told Naizer to face the Werewolf alone. Naizer requested that Creed let her go if he wins, to which Creed agrees. After Naizer defeats the Werewolf, he tells Creed to keep his promise. Creed keeps his promise, literally, and drops Rinslet off of the tower.
Also done in the original series, in a much more straightforward way. When Piccolo is confronting the king of East City on his airplane, he grabs the king's first mate and holds him over the edge. The king demands that Piccolo let him go, and Piccolo does just that, letting the man fall to his death.
Played with by Doctor Doom in the "Unthinkable" arc of Fantastic Four. Doom is holding Franklin hostage in hell, and holding the arm of Valeria. He promises to let Sue's child go if she'll do what he wants, and when she acquiesces, he releases Valeria's arm. She's in no immediate danger, though. The current authorwas deconstructing Doom's Noble Demon habits.
Molly from Runaways shows an awareness of this trope. When a giant is holding one of her friends she follows the demand that the giant put the friend down with "And not, like, down your throat."
In one issue of Suicide Squad, Amanda Waller sent Deadshot to stop the other villain Rick Flag from killing a Senator, with the orders that "Rick Flagg must never be allowed to kill the Senator, by any means". Deadshot made sure he'd never be able to kill the Senator - he killed him himself. I guess that teaches you not to give vital jobs to the Axe CrazyPsycho for Hire...
The Dark Knight: The Joker does this with Rachel. Luckily it wasn't a sheer drop he was holding her over, so Batman has time to save her.
"You want down? I'm good at down! I'm really good at down!!!"
Hancock, right before slamming some criminals' car into the Capitol Records Building.
In Pirates of the Caribbean: The Curse of the Black Pearl, Will demands of Barbossa that he release Elizabeth. However, he "failed to specify when or where" to quote Barbossa, resulting in her being forced to walk the plank. They were near a deserted island though, so she didn't drown.
In Analyze That, Paul Viti and his bodyguard, Jelly, are interrogating a snitch, which leads to this exchange after they get their information.
Paul: "Alright, pull him up."
Jelly drops him.
Paul: "What're you doin'? I said pull him up."
Jelly: "No, you said drop him."
Paul: "No... I said pull him up!"
Jelly: "I specifically heard you say drop him!"
Paul: "No, you heard what you wanted to hear."
Jelly: "... you got me there."
This happens near the end of Enchanted, while Robert attempts to protect Giselle from dragon-form Queen Narissa:
Robert: Over my dead body!
Narissa: ...OK. I'm flexible.
Freddy pulls this one in A Nightmare on Elm Street 3: Dream Warriors. When the heroes show up to save Joey, who's tied up over a fiery pit, Nancy (who, having fought Freddy before, should reallyknow better) shouts "let him go, Krueger!" Of course, Freddy replies, with a sarcastic bow, "your wish is my command": Joey's sent plummeting into the pit, and is only narrowly saved by the rest of the group.
This happens in the Disney/Walden Media movie version of The Chronicles of Narnia: Prince Caspian. When some Telmarines are about to dump Trumpkin, bound and gagged, into the river, Susan shoots an arrow and orders them to "drop him". They do so - unsurprisingly, into the river, and the boys jump in to save the dwarf while Susan dispatches the soldiers. Trumpkin is suitably unimpressed, and treats Susan to a bit of snark once they're all back on dry land.
In a movie about the Dutch occupation of Indonesia, some soldiers have a prisoner tied upside down and are torturing him. An officer orders them to let the man go, so they cut the rope so he falls on his head and breaks his neck.
Semi-heroic example in Max Keeble's Big Move: when Max tells the nerds to "let the bullies go" after threatening to throw them in a dumpster, they comply... by dropping them in the dumpster.
In The Toxic Avenger, when Toxie confronts the hit-and-run driver Bozo in Bozo's car, the youngster tells Toxie to "give him the wheel" so he can drive straight. Well, Toxie dislocates the steering wheel and hands it over. Cue Oh Crap look on the driver's face - and a collision-induced explosion.
In Underworld: Rise of the Lycans, Viktor seizes a dissenting (Human) silver mine owner by the throat. The man croaks "Let me go." Viktor complies, hurling him headfirst into a massive stone pillar and splattering his brains.
Underworld: Awakening has a heroic (put loosely) version of this. Selene is using a High-Altitude Interrogation on a mook that let her escape from the facility so they could use her to find Subject 2. After the mook explains this and tries to get some mercy by saying he "let her go", Selene quips "now we're even" and drops him.
A variation in the film of A Series of Unfortunate Events occurs when Count Olaf has Sunny hanging in a cage. Violet tell him to let her go... that's the exact order he relays to his underling. Needless to say, the children had him hold that order in a hurry.
In Wishmaster 2, the Djinn traps Father Gregory in his hellish home, suffering at the cross like Jesus. When Morgana wishes for the Djinn to release him, the Djinn drops Gregory's tortured body to the floor. Morgana protests that he didn't fulfill the wish, and the Djinn responds by releasing Gregory from his life.
In The Lone Ranger, Butch Cavendish grabs Rebecca as a hostage during the final battle. When the Ranger orders him to let her go, Cavendish threatens to drop her off the side of the moving train. Subverted when the Ranger tells him to do it as she always seems to land on her feet. And then the trope turns out to be invoked: when Cavendish tosses her off, she lands right on Silver.
Blofeld: Put me down! Put me down! Bond: Oh, do you want to get off? [pushes Blofeld to his death]
The Amazing Spider-Man 2 has Peter making this mistake when Green Goblin takes Gwen and holds her over the roof of the clock tower. This starts the chain of events that ultimately leads to Peter's I Let Gwen Stacy Die moment.
A variation in The Arctic Incident. When Briar Cudgeon has Artemis as a hostage, and is told to put Artemis down, he responds by cocking his gun and sneering 'I'll put him down alright.'
In one episode of Babylon 5, Delenn demands that the Streibs release their prisoners, and they do: into outer space.
Played for humor on an episode of Get Smart. The Chief yells, "Drop that Control agent!" to some henchgirls holding Max out a window; Max later points out that his words could have multiple interpretations.
Whenever Stephanie is kidnapped by the "evil dude" in LazyTown, this command is used, one of which had Hulk Hogan forcing the "evil dude" to let her go.
Combined with Literal Genie, the GURPS manual has a spell to animate a machine or vehicle, but warns you it takes you commands literally. Saying "Drop me off there." to an animated helicopter is specifically mentioned.
In Star Wars: Bounty Hunter, Jango Fett is holding a senator over the edge of the balcony of his penthouse apartment. A police ship appears and orders Jango to release the senator. Jango complies.
In Batman: Arkham Asylum, Batman confronts the Joker; they are separated by a pool of water. Joker's holding a guard hostage, and Batman orders Mistah J to let the guard go, which the Joker does. After he kicks a generator in the water and moves the guard over the water. If you sequence break by cutting power to the pool before heading to it, the guard's already dead.
In Forever's End, the Black Demon is holding Hyuuga over a cliffedge, and Epoch tells it to let him go. Splat.
Sonic Lost World: In the opening cutscene, Sonic and Tails are chasing Eggman as he's making off with a capsule filled with innocent animals, and Sonic orders him to "Drop the critters!" Eggman replies, "If you insist," and proceeds to do just that.
Tails: "Whoa! That's harsh!"
In Nightmares from the Deep 3: Davy Jones the title villain promised not to kill the main character if her teenage daughter signed a contract with him. When she did he replied "See, I never meant to kill your mother...it's the ocean that will!" and pushed the main character off the plank.
Sam Starfall, from Freefall, does it to himself and as a result gets dropped into a garbage bin by the people who caught him cheating at cards, here, complete with a Lampshade Hanging.
The pilot of Darkwing Duck, with Gosalyn being held high in the air by the villain's vulture (or condor or something) to force Darkwing to give up the code for a weapon. Saved by Launchpad, who happened to be flying by when the bird let go.
Or was actually following the events and reacted appropriately.
In Chip 'n Dale Rescue Rangers, "Adventures In Squirrelsitting", Fat Cat holds Tammy and Bink by their tails, and demands the Maltese Mouse in exchange. Said artifact is given up, followed by the demand, and the literal fulfillment. Monty catches Bink (with an assist from Dale), and Chip catches Tammy, setting her up to be the Clingy Jealous Girl for an episode.
In the Pinky and the Brain episode "Brain Noir," Brain is climbing out of the water and grabs the hand of someone reaching out to help him. Then he realizes that the person in question is his archnemesis Snowball and yells, "Get your hand off of me!" Snowball, not unexpectedly, complies.
Done in The Tick vs. Pineapple Pokopo when Arthur is captured by some mooks. Of course, Arthur can fly, but he isn't particularly happy about The Tick's choice of words either way.
A less-fatal version of the "let me go" variation is used in The Prince of Egypt, in which Moses does this to Tzipporah, releasing the rope with which she's tied and allowing her to fall into a pool of water. She later returns the favor.
Heroic (of a sort) version in Robot Chicken. Ted Turner, having dressed himself as Captain Planet, forces someone to sign a pledge not to dump any more sludge by holding them out of a skyscraper window, after which he will let them go. The guy complies, and Turner releases him.
Self-inflicted version: In Batman Beyond: Return of the Joker, Ghoul captures Dana on a ledge in a several-story nightclub. While struggling with him, she tells him to let her go. He does, and she falls two stories onto a strobe light.
This happens at the end of the VeggieTales episode "Sweetpea Beauty" when the mirror drops Sweetpea from the top of the castle. Prince Larry saves her, though.
Batman: The Brave and the Bold: In "Legends of the Dark Mite!", Catman is auctioning off a wild Sumatran tiger. Batman demands that Catman "Release him!". Catman obliges by opening the cage and letting the tiger loose on Batman.
In "The Long Arm of the Law!", Kite-Man has Plastic Man's family tied to a kite that he is flying into a thunderstorm. Batman tells him to "Release the hostages!" and Kite-Man releases the tether line, sending the kite soaring into the storm.
In SWAT Kats, Madkat takes a hostage on the roof of a skyscraper. The Enforcers order him to "put him down" and Madkat drops him over the side. Razor and T-Bone save the hostage in time.
In the Transformers Generation One episode "The Search For Alpha Trion", as the Decepticons dangle Optimus Prime over a vat of acid. Elita One saves him by freezing time and pulling him to safety.
Elita One: Please, let him go.
Starscream: Very well, my dear...let him go...into the acid!
The Secret Saturdays: In "The Vengeance of Hibagon", Professor Mizuki is holding a crimelord over the edge of a building when Drew orders "Let him go, Mizuki!". Mizuki comments on the poor choice of words before dropping him.
Penelope Pitstop for example: "Let her go, Zorro!"
Happens twice in the Grand Finale of Action Man (the 2000 series). The first time this trope is played completely straight; Action Man demands Professor Gangrene lets Rikkie go while the former threatens to throw the later out of the airship. Gangrene is more than happy to comply with this request. The second time, when Quake threatens to throw Fidget into a lava pit, Action Man is more carefull with his choice of words and specifically demands he puts her down safely on the ground. Not that it stops Quake from throwing her into the pit anyway.
In 2010, Russian naval forces arrested a group of pirates that had taken over an oil tanker. However, due to what they saw as irregularities in international law, they had to release them. So they did - they were "released" into an inflatable boat, hundreds of miles from land and with no navigational equipment.
In 1952, police officers moved to arrest burglars Derek Bentley (age 19) and Christopher Craig (age 16) at a time when Craig had a revolver. Supposedly, after getting away from Detective Sergeant Frederick Fairfax, Bentley told Craig, "let him have it, Chris," which can be interpreted as an instruction to turn over the gun or an instruction to shoot. Fairfax was shot in the shoulder. Shortly thereafter, Police Constable Sidney Miles was sent onto the roof and fatally shot. Craig and Bentley were found guilty of murder, Bentley was executed, and the execution was so controversial that it arguably led to the abolition of capital punishment in the U.K. In 1998, Bentley's murder conviction was posthumously quashed.