Quotes: Cool and Unusual Punishment

Yours is an agony worse than all others! You will remain in here for eternity listening to... whiny protest songs from the Sixties!

Harlan Traub: Mr. President, I know you have a thousand things on your mind, but I would just love to talk to you about how to revolutionize the food processing industry!
Frank Underwood: [to the audience] Please, slit my wrists with his butter knife.

Cultist Assassin: Oh I know what's going to happen here. You'll start making threats that you're going to do something horrifically violent to me. But then you'll pull something ludicrous out of your arses, such as making me watch Battlefield Earth on DVD, or threatening with mime artists, or perhaps making me go over the Inquisition tax return.
Inquisitor Syrus "Virus" Zuviel: Actually, we were going to have Lothar here cut your bollocks off, then start asking you some questions.
Exterminatus Now, subverting expectations in the cruelest way possible

I punished Timmy by making him eat chocolate, which in retrospect, wasn't such a good punishment after all.
—-Mrs. Turner, The Fairly Oddparents: Channel Chasers

"My brain agrees with you. My gut is telling me to jack his suit's olfactory filters so that everything smells like refuse."
"Remind me never to get on your bad side."
Tali'Zorah vas Neema and Garrus Vakarian, Mass Effect 2

My object all sublime
I shall achieve in time
To make the punishment fit the crime”
The punishment fit the crime;
And make each prisoner pent
Unwillingly represent
A source of innocent merriment!
Of innocent merriment!

I am going to give you such a movie!
Pearl Forrester of Mystery Science Theater 3000, sentencing Mike and the Bots to Hobgoblins after they jump on her couch

Cluny, as of this point every unhelpful word from your mouth earns you an hour in the Death Pit Theatre watching Care Bears reruns!
Miss Minty, The Official Fanfiction University of Redwall

Crushing's too good for him. First, he'll spend a year in the incinerator. Year two, cryogenic refrigeration wing. Then ten years in the chamber I built where all the robots scream at you. Then I'll kill him.
GLaDOS, Portal 2

Snivley, Sonic Sat AM, preparing Escargot in the most diabolical manner possible.

Oh, no! The Princess is being forced to listen to a debate by two Fryguys about the names for the little things on the end of your shoelaces!
Super Mario Bros., Nintendo Comics System story "You Again?"

Personally, good sir, I've never been in favor of the ban on unusual punishment.
Llewellyn, Ozy and Millie, during jury selection