Hilariously subverted in an old episode of Adventures of Sonic the Hedgehog. Sonic turns up and impresses all the locals (who are sheep) with his speed, and Robotnik builds a massive race-course and challenges Sonic to a race, then convinces all the sheep (all of them) to bet all their money and then some on Sonic... and then kidnaps Tails, forcing this kind of choice (Sonic either throws the race, or Tails gets it). He then turns the completely broke sheep into his slaves, the scene shifts to an Egyptian style environment where the sheep are as slaves building pyramids... and then Sonic and Tails turn up and completely wreck Robotnik.
In the Avatar: The Last Airbender episode "The Library", even fighting 'blind' Toph could have probably made it more trouble than it was worth for the sandbending bandits to make off with Appa... but she was the only thing keeping the library containing her True Companions from being dragged beneath the dunes.
In The Legend of Korra episode "A New Spiritual Age", Korra is presented with an even more sadistic choice by Unalaq. Either she opens the Northern Spirit Portal, enabling Bigger Bad Vaatu to escape from his prison when the Harmonic Convergence comes, or he'll kill Jinora by destroying her astral body. Korra is horrified, but chooses the first option.
In the final episodes of Book 3, the Arc Villain Zaheer presents Korra with another sadistic choice after he and the rest of the Red Lotus take the new Air Nation hostage. Either she hands herself over to him, or he'll wipe out the Air Nation. She chooses the first answer, though neither party intends to play fair.
In Book 4, Kuvira gives Korra the choice of leaving Zaofu peacefully or stay and possibly watch Zaofu and her friends fall.
In Barbie in a Mermaid Tale 2, Merliah must choose whether to lose her legs and stop Eris or keep them and let Eris take over again.
Ben 10's enemies love putting him through this — Ghostfreak telling him to put down the gun or he'll kill Gwen, Vilgax demanding the Omnitrix or he'll kill her... In the Alien Force episode "Primus," Vilgax steals the Omnitrix, dangles the trio over the Codon Stream, and tells Ben that he'll have to show him how to work the Omnitrix to save his friends... and still die afterwards regardless. note Ben only gets out of the latter by Tricking the Shapeshifter, which a terrified Gwen didn't realize until the last minute.
In Deadly Ransom, when Captain Planet is taken prisoner, the Planeteers' one option is delivering the ransom (which is nuclear waste) and the other - letting Dr. Blight and Duke Nukem kill the Captain. They find a third solution.
In Summit to Save Earth, Part I Zarm makes Gaia choose to either stop him from wrecking the Earth Summit or save the Planeteers, whom he has just trapped in a polluted tornado. Being in the Mama Bear mode, Gaia starts with rescuing "her" kids. Unfortunately, when she checks on Ma-Ti, she stops paying attention to Zarm who uses this very moment to attack her.
Zarm: Wrong choice, Gaia! Now you lose it all!
Fat Cat pulls this in an episode of Chip 'n Dale Rescue Rangers, simply by threatening to drop two squirrel children as a way to coax the Rescue Rangers into handing over a statue. This might also count as an example of Would Hurt a Child, seeing as he has no problem with placing two children in danger.
In the Code Lyoko episode "Ultimatum", XANA possesses the principal and abducts Odd and Yumi. The remaining Warriors have to choose to either hand over Aelita to XANA (which would result in her death and eventually the potential deaths/enslavement of the world) or allow XANA to "liquidate" Odd and Yumi. Ulrich's attempt at a third option (taking an EMP bomb Jérémie showed off at the beginning of the episode to disable XANA after locating where he's keeping Odd and Yumi) is derailed by the bomb shorting out his mobile phone so neither Jérémie nor Aelita know if he has succeeded in his rescue or just given XANA another hostage.
In Donkey Kong Country episode "Speed", Diddy and Dixie Kong end up on a mine cart without breaks that has a bomb that will explode if it does stop. (Sound familiar?) This means DK has to choose between saving his friends and sticking around to protect the Crystal Coconut. He finds a compromise; take the Coconut with him as he goes off to save his friends!
Peter: Okay Brian, here's a riddle. A woman has two children and a homicidal maniac makes her choose which one he will kill. Which one does she choose?
Brian: That's not a riddle. That's just terrible!
Peter: Wrong! The ugly one!
Another scene has Peter asked whether he would save Chris or Meg from a homicidal maniac. He says to ask Lois since he isn't good with tough decisions. The cutaway shows him at a video store, unable to choose between renting "Ernest Goes to the Beach" and "Ernest Doesn't Go To The Beach".
At the end of the first 5-part episode of Gargoyles, after Demona turns against them, a misfired rocket launcher sends both her and the gargoyles' new friend Elisa over the edge, Demona apparently unconscious and unable to glide to safety. Goliath can save either his mate (his former mate who, at the time, he still cared for) who had betrayed him, or the human they just met who nevertheless had been honorably on their side. He chooses Elisa; though howls afterwards at Demona's "death." (Later we find that it's a lot harder to kill Demona than that.)
Evil-Lyn: It looks like those gorgeous muscles are completely useless!
There is a flaw in her plan, but ironically, her taunt is what makes him see it; to access the third option, he has to leave and come back as Adam.
Kim Possible plays this when Adrena Lynn makes Kim save both Ron and Brick in this manner. She manages to save them both with ease.
Discord of My Little Pony: Friendship Is Magic gives one to Rainbow Dash when she encounters him in the labyrinth where the Elements of Harmony are hidden. Discord shows RD that her home Cloudsdale is on the verge of collapse due to her prolonged absence in the labyrinth and thus presents her with the wings that he took from her to prevent her from finding the Elements of Harmony the easy way. Discord gives her the choice of either continuing to wander the labyrinth aimlessly and allowing Cloudsdale to collapse due to her negligence or throwing the search for the Elements and recovering her stolen wings to prevent Cloudsdale's destruction. Rainbow Dash chooses to abandon the Elements and her friends in favor of saving Cloudsdale, thus allowing Discord to rule Equestria with an iron and chaotic fist.
This is also played in an interesting twist; it doesn't matter what she chooses, as any of the options will make her go against her Element of Loyalty, which is exactly what Discord wants. He wins either way.
And he brainwashes her just to make sure she does what he wants, so there was never really any choice in the matter. He just presented the situation to her out of sheer sadism.
If you watch closely, Dash never even gets the chance to choose; he does the Finger of Death like he does with Fluttershy. Whereas the other three ponies fell by their own, the two ex-pegasi were directly touched and thus directly brainwashed - in Dash's case, before she could even make the choice and was still torn.
Then again, Rainbow Dash didn't successfully overcome Discord's machinations the way Fluttershy did. Just like his earlier torments of the other ponies, the point of the sadistic choice was to demonstrate the flaw in her Element - namely, that it's sometimes impossible to properly disentangle oneself from a web of conflicting loyalties. Thus, all that Discord sought was for Rainbow Dash to be torn over the decision in the first place, at which point he brainwashed her into betraying her friends.
On the Phineas and Ferb episode "The Beak", they have to choose between rescuing their friend Isabella or a crowd of random spectators from the villain of the week. Fortunately, each brother can split up and go save them both.
Parodied in South Park when Towelie has the choice of keeping the boys from falling into an acid tank or getting high. He chooses both by stretching over to get the joint.
Spider-Man loves this trope. Spider-Man: The Animated Series has Green Goblin do a similar trick as in the movie 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.
Teen Titans: "If you join me, if you swear to serve me, if you never speak to your friends again, I will allow them to live."
A Moment of Awesome not only for Slade, but for the Titans when they figure out what's going on themselves.
In one of the annual Halloween episodes, Lisa has been given a slot on a spaceship escaping a doomed Earth, but is informed she can only bring along one family member. Lisa instantly chooses Marge, leaving Homer and Bart behind to die.
In the Transformers AnimatedPilot Movie, Starscream pulls one of these to show that the Decepticons in this series are no laughing matter: after giving the Autobots a sound beating, he shoots Bumblebee, critically wounding him (and he was actually aiming for Sari; Bumblebee took the hit), tosses him into a train car that holds the Mayor of Detroit, the human sidekick's father, and various other civilians, then flies it to the top of a building, giving the Autobots one megacycle (about an hour) to surrender the All Spark to him before he kills the hostages and, to raise the stakes even more, attempts to take the All Spark the hard way, cutting a swath of destruction across the Earth until he finds it himself. And to complicate things further, none of these Autobots can fly... So the third option involves using the All Spark as bait while they attempt a rescue mission.
In the three-part "The Ultimate Doom" episode of The Transformers, Megatron plans to bring Cybertron into Earth's orbit in order to destroy Earth and harvest the energy. If the plan fails, however, Cybertron will be destroyed. Megatron forces Optimus Prime to choose which planet will be lost. Luckily, Prime thinks of a better solution.
Lampshaded ("Great. The old 'save your partner or lose the weapon' gag") and served with extra sadism in Armada. The "partner" turned out to be The Mole.
Transformers Cybertron Starscream has gone on a Foe-Tossing Charge, being a Determinator in the extreme in the process, and beaten all of the Autobot army to seize the Omega Lock and Cyber Planet Keys. Optimus Prime manages to knock them from his grasp (and knock out Screamer in the process). Starscream recovers to see the artifacts nearly back in Prime's hands... so he fires a missile at the human companions and the Recon Mini-Con team. Optimus has to change course to both shoot down the missile and block the blast, enabling Starscream to purloin the MacGuffins. One might briefly wonder why Jolt didn't warp them out of harm's way, but then one remembers that A. Jolt is panic-prone, and B. Creating dimension gates is a strain on him, and he'd already done it twice just a couple minutes before, the second time moving a rather large Autobot to safety.
Winx Club has an episode in season 3 where half the girls are sent into a maze to retrieve the water stars which will supposedly save the world from Valtor. However, inside the maze, the girls are tempted with an example of this trope.
Tecna is given two choices; she can obtain the magical item, BUT...If she chooses to do so, she will have to give up her emotions, abandoning her friends and boyfriend and not being able to feel any feelings at all again. Or, she could choose to leave, inevitably dooming every realm in the universe, leaving her responsible.
Musa probably has the most sadistic, played straight version of this trope; she has the decision of seeing her dead mother again and bringing her back to life, but if she decides to do so, she is in effect responsible for the apocalypse.
Stella can save the world with the water stars... if she gives up her FREAKING FACE.
One episode of the Secret Squirrel segment of 2 Stupid Dogs had a race car driver named Hot Rodney attempt to prevent Secret Squirrel from beating him in the race by having his mechanic kidnap Morocco Mole and have him tied up somewhere far from the racing track with a belt of dynamite strapped to him, forcing Secret to choose between rescuing his friend at the cost of losing the race or beating the race while letting his friend die. Secret manages to rescue Morocco, and while he loses the race in the end, he tricks Hot Rodney into wearing the dynamite belt that was strapped to Morocco in order to give the villain some last-minute comeuppance.