Past a certain point, they all suck. Being drawn and quartered sounds pretty bad, although that wood chipper/feet first thing sounds worse.

EDIT: Then there was Vlad Tepes, Vlad the Impaler, a feudal warlord of Wallachia, an ancient region of what is now Romania. Vlad, is, of course, Bram Stoker's inspiration for "Dracula", although Vlad Draculya differed markedly from the rather urbane, polished, Hollywood Bela Lugosi version.

In her wonderful book, "The Historian", Elizabeth Kostova" describes Vlad as "...the Wallachian prince, a fifteenth-century ruler, hated by the Ottoman Empire and his own people - both. Really among the nastiest of all medieval European tyrants. It's estimated that he slaughtered at least twenty thousand of his fellow Wallachians and Transylvanians over the years....Actually, there is evidence that Dracula's father gave Dracula over to the Turks when he was a boy as hostage in a political bargain, and that Dracula acquired some of his taste for cruelty from observing Ottoman torture methods."

Vlad (or his henchmen) burned whole families alive. He buried people naked up to their navels, and shot at them until they died. His nickname, Vlad the Impaler, comes from the grisly torture of impalement - shoving a sharpened wooden stake up through the body's genital or anal area with such force that it emerges from the victim's mouth or the top of his/her head.

American television. No thank you.

Yanni!

I'm just kinda winging it here, but I'd have to say having you're skin peeled of and then being rolled in salt.

According to an exhibit I saw (I think it was at the Amsterdam Torture Museum, or it could have been the Clink Prison museum in London), the most painful torture method was being boiled alive. I'm not sure how they knew this, maybe they boiled people and asked them how painful it was on a scale of 1 to 10?

Here are a few interesting sites about medieval torture (gruesome! don't read it while you're eating your breakfast)

http://www.livescience.com/history/top10_medieval_myths.html

http://medieval-castles.org/index.php

http://www.fidnet.com/~kawlaw/medieval.html

http://en.wikipedia.org/wiki/Torture

http://quizilla.com/.../



Footnote- I have made this post mostly about medieval torture because they were (IMO) the most imaginative when it came to inflicting pain. My eyes are watering just reading some of those links!

Crucifixion.

Hmmm...
Well, there's physical pain, which is bad, and then there's psychological pain, which is always much worse.

The worst form of mental torture I can think of is to be strapped down and forced to watch while all your closest friends and loved ones are tortured and killed in the most physically agonising way possible.
Or worse yet, being forced to inflict that torture upon them yourself.

Uday and Qusay Hussein fed people into a wood chipper, feet first. Compared to that boiling is mild.

My neighbour was a POW in a Japanese camp WWII and he said the worst torture was when they force-fed the prisoner rice until his stomach was full and then force-fed him water so that the rice expanded.

Being forced to watch Reno 911 or The Office.