There's a joke about a man who died and went to Hell. For his punishment, he was shown two rooms, one showing the man whipped and beaten mercilessly and another one showing the man strapped to a bed while a beautiful woman had unending rough sex with him, and was told to pick which punishment he wanted. He decided to choose the latter option. The punchline involves the woman walking up to the man and saying, "Hey, thanks for taking my place."
Another variation of the joke gives the man the choice between a torture chamber with hot pokers and a room with a group of people enjoying a cup of tea while standing in knee-high excrement. The man chooses the latter option and steps into the room, expecting to be handed his cup of tea. Just then, the leader yells, "Right, lads, tea break's over. Back on your heads!"
One of the adventures of Abelard Snazz, The Man With The Two-Story Brain, written by Alan Moore for 2000 AD had the title character punished by the gods themselves and forced to solve a Rubik's Cube.◊
After Judge Dredd assassinates a brainwashed Chief Judge Griffin on live television and escapes during the "Apocalypse War" Story Arc, all East-Meg Judges present throughout the incident have been rounded up and are about to be issued winter clothing before being sent off to a penal colony in Siberia, which is War Marshall Kazan's typical punishment for failure.
Kazan: Cancel that order!
East-Meg Judge: You mean you're not sending them to Siberia?
Kazan: No, I mean they're not getting any winter clothing!
In Turnabout Storm, murder is shown as a very rare and serious crime in Equestria, and the punishment for the guilty is banishment. Phoenix immediately thinks it isn't as bad as in his own world; that is, until Twilight goes into more detail:
In Mirrors Image, Twilight decides to punish one of her changling guards by naming it Sucker Punch. Although this crosses over into Cool and Unusual Punishment, most changlings prefer to not be named, and thus, being named really is that bad.
The Stalking Zuko Series, Fridge Logic would dictate that the cooler punishment in the Boiling Rock would be driven useless by any firebender that can keep oneself warm or has a resilience to cold. Not so much when the extreme temperature differences causes the prisoner to catch "cooler fever" and has to defend oneself while made horribly ill by the other prisoners and the guards.
In Idiocracy, Joe is sentenced to one night of rehabilitation when his decision to irrigate crops with water caused population riots after the price of the Brawndo Corporation's stock plummeted. It turns out that "rehabilitation" is a type of public execution modeled as a Squash Match with Homicide Machines.
Woody Allen's film Take the Money and Run has a pretty nasty punishment that's made even more harmful. As the narrator states, "Food on a chain gang is scarce and not very nourishing. The men get one hot meal a day... a bowl of steam."
Which is then shortly followed by an inverse of the trope, a man who didn't give a good day's work is hauled into another room, and the warden takes Virgil over to show him "what he's got to look forward to." We see the the shadow of what appears to be the man tied to the ceiling being whipped by another guard (and sounds of whipping and the prisoner wincing seem to confirm this), but after Virgil and the warden walk through the door, we find out that the guard is whipping the prisoner's shadow, instead.
In The Dark Knight Rises, Hanging Judge Jonathan Crane gives Gotham's wealthy the choice between death and exile. Those who choose exile must leave Gotham...by walking over thin ice. Though, those that choose death are sentenced to execution...by exile.
In Return of the Jedi, Jabba sentences Luke and Han to be fed to the Sarlaac. Han quips that it doesn't sound so bad, until C3PO translates the bit about, "in his belly, you will find a new definition of 'pain and suffering' as you are slowly digested over a... thousand years."
Han: On second thought, let's pass on that, huh?
In Terry Pratchett's Going Postal Moist Von Lipwig is offered (as an alternative to being hanged, again) the job of Postmaster General. It's a job for life, just quite possibly not for long as it's already claimed the lives of several other "volunteers".
Lord Vetinari loves doing this. Just previously, he'd informed Moist that if he didn't accept the terms, Moist could just walk out that door over there and never hear of this again. Naturally, it opens onto an extremely deep pit. The villain actually chooses that option given the same choice.
The next time Moist appears, he thinks he's getting the same treatment. So he borrows a pencil from Drumknott and gently tosses it through the door... and is shocked to discover a floor, much like the one he's firmly standing on, at approximately the same level. He's got the Post Office running like clockwork; what kind of moron does he think Vetinari is, gambling Moist's life like that when he's already being put to good use?
Also inverted in a joke used both in Guards! Guards! and Feet of Clay, in which it's mentioned that dwarfs punish thieves by "hanging them up by the...town hall. Sometimes for days.".
In Robert A. Heinlein's Have Space Suit – Will Travel, Kip is told that the evil race will get their home planet rotated. He wonders why the crowd hearing the sentence sounds shocked and upset about that, since all planets rotate. It is then explained to him that the planet will be "rotated 90 degrees out of space-time" which puts the planet alone in a private universe. Which he thinks is not good but not worthy of getting that upset about. Then he finds out the planet doesn't get to take their sun with them...
In William Gibson's Neuromancer, In Case's back story, his former employers let him keep the money he stole from them... because he'd need every cent after their brand of retribution completely damages his central nervous system leaving him unable to use his brain-computer interface to access cyberspace (and unemployable in his old profession).
In Spaced, Tim, unable to cope with The Phantom Menace, is admonished by his boss for getting cross with a child who wanted to buy a Jar Jar Binks doll. When he asks his boss what he's going to do about his behavior, his boss responds, "I'm going to have to let you go." Tim, relieved that he's being let off the hook when he thought he was going to be fired, takes a brief moment before understanding that firing him is exactly what his boss had intended doing all along.
Happens in Scrubs in "My Soul on Fire, Part 2" where the Janitor punishes J.D. for convincing everyone to come to his wedding on such short notice by keeping him at the top of a lighthouse for ten minutes...
J.D.: But that doesn't explain why these fish are taped to my hands!
Cue the flock of seagulls hungry for fish.
On Perfect Strangers, a Myposian acquaintance of Balki's challenges Larry to a duel. Larry accepts after Balki tells him it involves boxing the loser's ears. Then Balki explains to Larry that in Mypos, "boxing one's ears" means putting the ears in a box.
Doctor Who: At the beginning of the Key To Time arc, the Doctor asks what will happen to him if he refuses the White Guardian's order to find the parts of the Key, and is surprised by the answer of 'nothing'. The Guardian placidly clarifies "Nothing at all. Ever."
In The Happiness Patrol arc, standard punishments are doled out by the Kandy Man, who loves "happy" and typically sweet-themed executions, like having molten-hot sugar poured down your throat until you either suffocate or are boiled alive.
On My Wife and Kids, a lot of the father's punishments are like this. In one episode when his daughter Claire eats his halftime pie but none of his kids tell him who did it, he feeds them all only pie as punishment. They quickly figure out that there is a reason that dinner is more than "just desserts."
You Can't Do That on Television: One sketch had a child being 'grounded' and having his shoes taken away. The kid points out that having his shoes taken away won't stop him leaving the house. The adult then says that the child has misunderstood. Now that he has taken off his rubber-soled shoes, he is 'grounded' and hands the kid a live electric cable...
Inverted in one episode of Babylon5. Delenn tells Sheridan about a Minbari custom, and what precisely a woman can do to a man who tries to abuse the custom:
Delenn: She can even cut off his...oh, what is the human word for it...
[Long pause while Delenn tried to remember the word and Sheridan gets an absolutely terrified look on his face]
In Demon The Fallen, each house of the rebellious angels were each given severe punishments for their act. For example, the Slayers, The Grim Reaper house, were now forced to reap humanity as well as the other forms of life. The first house, the Devils... were given a harsh name. And that was it. This actually stung them deeply; as the first house, their task was to ferry God's word to His creation, and they weren't even worthy of a punishment.
Used in a third-person fashion, quite likely ripped from Futurama, in Questionable Content. Hanners is checking some bookkeeping for her Corrupt Corporate Executive mother, trying to find the source of an error. Marten asks her what will happen to the employee who made the mistake once he's found, and Hanners replies that he'll be fired.
Marten: Oh, that doesn't sound so...
Hanners: Out of a cannon, into a volcano.
Schlock Mercenary: The Robot King making clear that the mad-scientist-for-hire is not to touch the computer systems containing the King's brain:
LOTA: Should any of you even approach those systems, LOTA would be required to fire you. Kevyn: Okay, I get it. LOTA: Out an airlock.
The Spanish-language webcomic ''A Friki's life" does this in a strip when a man sent to Hell is forced to choose between being tortured, or having sex with a chicken for all eternity. After he choses the chicken, it's revealed that it's a 2-meter tall chicken with a passion for BDSM.
At one point in Dominic Deegan, Stunt is exiled from a city that he wasn't particularly attached to. He mocks how weak the punishment is... and then realizes what the actual punishment constitutes - his best friend Bumper, who really liked the city, wasn't exiled. Suddenly Stunt's enthusiasm evaporates.
The Invader Zim episode "Gaz, Taster of Pork" ends with Dib demanding he be punished for putting a spell on his sister. He's given a crown of toilet brushes and ordered to clean a toilet. Feeling that the punishment is rather mundane, Dib takes one look inside the bowl and is immediately horrified by what he sees down there. Closing words explain that Dib is now cleaning the toilet with his head.
The titular room with a moose from the episode "A Room With A Moose" would also qualify. No one can understand how the moose is meant to be a menace, not even Dib, who points out it's a big moose, but really, just a moose...at which point Zim sends several walnuts into the room, and Dib sees the moose eating the walnuts...which horrifies him for some reason. Confusing to the audience, but evidently effective against Dib.
The page quote from Futurama, naturally. It comes from the first episode, making this trope one of the show's earliest gags.
A similar thing happened in a Simpsons episode where Homer portrayed King Henry VIII. He responds to Ned Flanders' (as Thomas More) objections to seceding from the Church by offering to canonize him. Cut to Ned being fired out of a cannon.
The episode "Lisa On Ice" features a daydream Lisa has where she worries that failing her gym class would greatly damage her reputation later in life. In the daydream, the Chief Justice of the United States learns this just before swearing Lisa in as the new President.
Chief Justice: I sentence you to a lifetime of horror on Monster Island... Don't worry, it's just a name.
Man: What he meant is that Monster Island is actually a peninsula.
A Quack Pack episode has aliens threatening Donald Duck with twenty lashes with a wet noodle. He laughs it off and tells them to make them fifty. Turns out the "noodle" is a giant, living, carnivorous worm.
In one episode of Beetlejuice Beej and Lydia (and others) are playing baseball in the Neitherworld. At some point it is announced that the game has changed to "Sudden Death", meaning that the losers will have to stand in the "Losers' Circle", an area enclosed by a rope. Beej is unimpressed (as he's been dorking around the entire game anyway) until the "circle" opens up into a fang-lined maw that belches a fireball into his face.
On Fairly Odd Parents, Timmy once had to brave the "horrifying trials" of the "sadistic" Yugopotamians; these trials include walking through a flowery meadow, hugging a teddy bear, and eating chocolate* To the Yugopotamians, these really areNot So Harmless Punishments: fun and nice things cause them actual physical harm. A later episode features Timmy cockily accepting another challenge from the Yugopotamians, expecting more of the same, only this time he has inadvertently signed up for a gladiatorial fight to the death. Subverted in that, when he's given the chance, Timmy suggests a ball pit as his combat arena and pillows as weapons, giving him the advantage.
Also on Fairly Odd Parents, during a halloween special, the Yugopotamians believe that Earth is preparing for war because of all the costumed (turned real) monsters. When confronted, Timmy announces that war is on, and as the Yugopotamians leave they drop a "P-Bomb". While others are worried, Timmy is not, and announces that the P stands for Piñata.
Porky Pig runs afoul of some leprechauns in "Wearing of the Grin", and is sentenced to wear...the Green Shoes. Porky at first is pleased at how well they fit, until they take control of his feet and send him dancing across the landscape.