At some point it will probably reach a limit where one needs to be unusually susceptible to pain to die an even more painful death.

Presumably there could have been a point where someone drifted gently off to wherever it is we all go, comfortable and surrounded by loved ones, and in their naivety everyone present thought "oh how awful".

Morbid curiosity piqued, has a person ever been spaced? (Not just vacuumed)

Oh, I'm hearing some cereal killer aspirations.

*No one is going to convince me it's spelt any differently

That's why psychological torture is preferred by a lot of "advanced interrogators".

Keep someone locked in the same uncomfortable position for days while you're blasting aggressive disorienting sounds and randomly flashing blinding lights in a room with mirrors.

Once in a while, take them and do a few hours of water boarding. Make sure they're constantly sleep deprived and can never get more than a few minutes of sleep.

Then when you do want to inflict physical pain, focus on the feet very slowly. Feet is one of the most sensitive areas. Slowly start peeling the skin or stick nails through the toes, or practice some electroshock therapy.

Honestly torture is terrifying. I recently read a long form article about it. Worst part is, our "civilized" governments still do this with some amount of regularity. Would be more civilized to put a bullet in the head.

Then think about near future where we can read thoughts (like 1984 where the "advanced interrogator" reads the protagonists mind to figure out what his greatest fear is) or even worse implant thoughts. They could implant images of you murdering your family or something. There's a lot of potential for some horrifying stuff.

That's why in some science fiction, see Warhammer 40K, they have technology that let you keep on feeling that pain long after you should be well and thoroughly dead. Honestly I'm not sure who's better at it, the Imperium or the Dark Eldar.

So perhaps the most painful death would be just before that threshold.

The guy that got stuck upside down in a cave for hours is pretty horrifying.

https://en.m.wikipedia.org/wiki/Brazen_bull

"The brazen bull ... was an alleged torture and execution device designed in ancient Greece. ... The bull was said to be hollow and made entirely out of bronze with a door in one side. According to legends, the brazen bull was designed in the form and size of an actual bull and had an acoustic apparatus that converted screams into the sound of a bull. The condemned were locked inside the device, and a fire was set under it, heating the metal until the person inside was roasted to death.

"Stories allege after finishing construction on the execution device, Perilaus said to Phalaris: "His screams will come to you through the pipes as the tenderest, most pathetic, most melodious of bellowings." Perilaus believed he would receive a reward for his invention. Instead, Phalaris, who was disgusted by these words, ordered its horn sound system to be tested by Perilaus himself, tricking him into getting in the bull. When Perilaus entered, he was immediately locked in and the fire was set, so that Phalaris could hear the sound of his screams. Before Perilaus could die, Phalaris opened the door and took him away. After freeing him from the bull, Phalaris is then said to have taken Perilaus to the top of a hill and thrown him off, killing him. Phalaris himself is claimed to have been killed in the brazen bull when he was overthrown by Telemachus, the ancestor of Theron."

How about acute radiation sickness?

My bet would be cartel torture with adrenaline to keep the victim awake.

I would imagine some of the worst are rare conditions that take you from the inside out. I can’t find reference to the name of the disease, but I swear I remember seeing a bone condition that caused spiky growths, almost like crystals, to form from your bones.

It would be slow and excruciating and you would beg for death long before it ever came.

*Münster uprising

I was extremely confused trying to remember if Dan did an episode about mustard. But yeah that ep was brutal and entertaining!