As shoe trends have changed drastically over the last few hundred years, one truth seems to remain: Heels can really hurt. Whether you’re teetering in six-inch Louboutins or in your sensible shoes, there’s a precariousness about even putting them on, which makes wearing them part of the fun. But historically, some heels are more torturous than most: Take, for example, the Spanish Inquisition’s Iron Boot, filled with boiling water, or the medieval foot press, reminiscnent of a panini-maker for your feet. And more recently, too, designers have innovated shoes that verge on the insane – elaborate pieces that are part style, part art, part fetish object. From Alexander McQueen’s amphibian Armadillo Heel to the completely unflexible Backwards Heels and beyond, click through our slideshow of the 50 most torturous, fascinating heels of all time.