Sophie's Choice, both film and novel. Upon arrival at Auschwitz, Sophie is told to choose which of her two children will go to the gas chamber immediately, and which will live for some time longer in the camp. Since the story is realistic, Take a Third Option doesn't come up. The movie was popular enough that the term "Sophie's Choice" is occasionally used to describe similar sadistic choices. This sort of thing did happen there, too, and before it, as described in the nonfiction book Treblinka. On leaving the ghetto, parents had to choose which road to send their children down, the left or the right. One of them led to another ghetto and hard labor; the other to the titular death camp. They were not told which was which. To make this even more awful, the first female and first Jewish Mayor of Pittsburgh, Sophie Masloff, spent money on trash cans with the words: "Sophie's Choice — A Clean City" on them. Seriously.
The 1993 film The Good Son, starring young Macaulay Culkin and Elijah Wood, ends in a scene with both boys dangling over the edge of a cliff. The mom must pick between saving her evil son (played by Culkin) or kindhearted nephew (played by Elijah Wood.) She saves Frodo.
A similar scene happened in the comics. Robin was given the choice to save either Batman or a judge from Two-Face. It's subverted when Robin chooses the judge, but forgets about Dent's obsession with the number two; there was a second trap in place and the judge was killed. Poor Robin never really had a chance.
In Batman & Robin, Mr. Freeze sets Batman up with the choice to either thaw a frozen Robin or apprehend him. He seems to already know Batman is going go with the former though, being Batman and what not, and trots away merrily before Batman can even choose, sealing his exit behind him
Happens several times in The Dark Knight, since the Joker loves these: Reveal Batman's identity, or people will die. Kill the accountant or I blow up a hospital. Save Harvey or save Rachel. Blow up the other boat or be blown up by them (or me). And arguably the worst — Break your "one rule," or watch Gotham's finest kill a child. True to form, he seldom keeps his word; lying about which hostage is where, and not knowing or caring what they actually choose, and screwing them over anyway. Joker doesn't just do this out of raw sadism, though, but the added intention of showing people that underneath everyone can be a monster like himself.
Robot Chicken deconstructs the above scene, making everyone on one of the boats either unable to get the gist, or acting realistically to a dangerous situation. The Joker ends up getting really frustrated explaining things and saying they can't make realistic choices, and then ends up getting knocked out by Batman while he's doing so.
By the end of the film, Two-Face has also bought into this trope, asking Gordon to choose which member of his family he loves the most, because that's the one whose survival he'll flip a coin over.
A similar situation happened with Gwen Stacy in the comics, but Spidey's attempt to Take a Third Option didn't go as well as it did in the movie.
Spider-Man loves this trope. The 1990s animated series has Green Goblin do a similar trick with pre-Black Cat Felicia Hardy and her mother. Here though Spidey saves Felicia and lets Mrs. Hardy fall, assuming Goblin himself would save her instead because he needed her for his scheme. He's right and both live, although Goblin gets away with her.
The Proposition is based entirely around this principle. In order to convince The Sheriff to spare the life of his younger, mentally handicapped brother, the protagonist must seek out and kill his older, violently insane brother. He tries to Take a Third Option by getting his older brother to help rescue the younger one, but it doesn't work, and by the end, he's the only one left.
The Saw series is full with them, especially the sixth movie, where William is forced to make these twice. The first time, he has to choose between a diabetic, middle aged mother and a healthy loner. He chooses the mother. The second time, he has to choose which two of his six junior associates will get off a deadly carousel and live. He saves a single mother and, inexplicably, another woman.
Although no kidnapping was involved, the choice faced by Princess Leia in Star Wars of giving up the location of the Rebel base or watching her home planet of Alderaan be destroyed by the Death Star was a perfect example. Especially since, in a notorious Kick the Dog moment that kicked Grand Moff Tarkin across the Moral Event Horizon, he ordered the planet destroyed anyway after Leia gave a false location in hopes of keeping the Rebellion alive. Tarkin's reasoning? "Dantooine is too remote to give an effective demonstration." Alderaan, on the other hand, was a core world.
There's also Lando Calrissian's deal with Darth Vader in The Empire Strikes Back. Things in the EU like the radio dramatization and an Infinities comic that involves him refusing make his line about "I had no choice. They arrived before you did." much clearer. He was Baron Administrator of a city of people, and to save it and get The Empire to leave, he had to betray a friend. Vader never mentioned the torture, or that Boba Fett would get Solo, and he lied about leaving Solo's friends on Cloud City. At some point during this Lando protested strongly enough that his city was explicitly threatened, and eventually he tried to Take a Third Option, which was... marginally successful. Things worked out well enough in the end.
In Punisher: War Zone, Jigsaw and his Ax-Crazy brother Loony Bin Jim give the eponymous protagonist a literal Sadistic Choice in the form of a Shoot the Dog scenario: if Frank chooses between killing either the Donatellis or Micro, the brothers release the ones who were spared, otherwise they just kill all three hostages. Although Micro offers himself to Frank to spare the Donatellis, the latter instead elects to Take a Third Option. He kills Loony Bin Jim instead, and Jigsaw retaliates by killing Micro. Although given Frank's last words to Micro ("You won't feel a thing, Micro") coupled with Micro's nod to Frank, it seems as if they both understood that no matter who Frank choose, all of the hostages would have been killed anyway; by eliminating Jim, it gave Frank a brief window of time to save the Donatellis. Once they are out of harms way, he then brutally makes sure that Jigsaw pays for Micro's death.
In the end of Mad Max, one of the people who killed Max's wife is trapped under a burning car. Max gives him a choice - sever his leg to escape, or die in the explosion. The choice is made off-camera.
The end of The Box. James Marsden's character can either shoot and kill his wife, or let their son live the rest of his life deaf and blind.
This tends towards Heroic Sacrifice as well. The husband is too distraught to make a decision, so the wife insists that she die so their son can have a better life
This also appears to happen over and over again and appears to serve to show that Humans Are Bastards. When Cameron Diaz's character presses the button, another women is shot by her husband for the exact same reason as above. When she dies, yet another woman is shown pressing the button. Strangely, it always appears to be women who are willing to kill a random person to get money. Unfortunate Implications.
Funny Games is made of these, including making a wife decide if the antagonists kill her husband quickly by gunshot, or slowly by knife.
A rare example of a villain finding himself having to make a Sadistic Choice happens in Minority Report: Anderton confronts Burgess, the inventor of Pre-Crime, about his role in the movie's events (including several murders) the day before Pre-Crime is scheduled to go nationwide, prompting him to pull a gun on Anderton. Anderton points out that the Pre-Cogs must have predicted his murder by now (they did) and that Burgess is now faced with a choice: if he kills Anderton, he gets halo'd for life but Pre-Crime goes national as planned. If he doesn't kill Anderton, he remains free but Pre-Crime is revealed as a fraud and Burgess' life's work is thus destroyed. Burgess takes a third option and shoots himself.
In The Pink Panther 2, the real Big Bad tries to escape by threatening to destroy the Pink Panther Diamond unless Clousteau lets her escape. Unlike most examples, however, he didn't need to Take a Third Option, as the "Pink Panther diamond" she was threatening to destroy, and thus had stolen earlier, was actually a decoy, something she didn't know.
Herod, villain of The Quick and the Dead, enjoys giving people a choice between killing someone they love, or dying at his hand.
In Captain America: The First Avenger, the HYDRA spy attempts to make Steve Rogers choose between going after him or saving a little boy he's held hostage. Before Steve can do anything, the spy tosses the kid into the water. As it turns out, the kid's a good swimmer, as he then encourages Steve to go get the spy.
In P2, Thomas, the kidnapper, gives Angela two choices in dealing with Jim, a drunken coworker who hit on Angela after a Christmas party: she can beat him to a bloody pulp or Thomas can ram Jim with his car.
Wreck-It Ralph has to make this choice at the request of King Candy: either destroy "Glitch" character Vanellope Von Schweetz's car, along with Ralph's friendship with her, or allow Vanellope to race, get on the roster, glitch, and have the game get pulled from the plug, which would kill her since she cannot escape to Game Central Station because she's a glitch. Only after he made his choice did he find out that King Candy wasn't entirely truthful and wanted Vanellope out for ulterior motives.
Plays with the trope in that King Candy only asked Ralph "to talk a little sense into her." Destroying the cart was a conclusion Ralph came to on his own.
in Se7en the unseen perpetrator of a number of grisly murders, disfigures a beautiful but vain woman, then gives her the choice: sleeping pills to kill herself or a phone to call for an ambuance. We figure out what choice she made as the police are examining her corpse.
In The Hobbit, the trolls tell the dwarves to surrender or else they will rip Bilbo's arms out. The dwarves surrendered.
An interesting case occurs during The Cabin in the Woods. The two main characters have to end up deciding between obeying an organization which sends dozens of people to their violent, miserable deaths every year via a cache of inhuman monsters, or disobeying the organization and bringing about The End of the World as We Know It via the real villains of the movie, TheAncient Ones. The characters end up choosing oblivion.
Man of Steel: Kill the rampaging Zod or allow him to kill innocents? Superman chooses the former.
In the backstory of Pacific Rim, Hercules Hansen faced this choice. During Scissure's attack on Sydney, he only had time to rescue either his wife or his son before they dropped the nuke. He chose his son, Chuck, who later became his copilot. They both hate him for it, although they usually take their anger out on the Kaiju.
Pitch Black: As part of Riddick's attempt to corrupt Fry and win her over, he presents her with an impossible choice. She can only convince him to go with her willingly to rescue the two others she left behind. Riddick however offers her to leave them to die and take off with him in the skiff instead. She can either die along with them, knowing that she's a good person but save no one or come with Riddick and live with the guilt for the rest of her life. What makes this worse is that as Riddick points out, there is no one to blame Fry for choosing self-preservation. She eventually does make a moral stand and convinces Riddick to help her, as her moral actions intrigue him.