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1993: Apple Newton
Was there any doubt that the Newton would be on this list? It's the quintessential before-its-time piece of technology: its utter commercial failure is undeniable, but its descendants are just as undeniably omnipresent.
The reasons for the Newton's flop are numerous: it was too big, it was too pricey, its handwriting recognition software was spectacularly unreliable, even becoming the subject of a series of Doonesbury comic strips. The Newton's more successful imitators are equally numerous, but the first was the original Palm Pilot, which had the clever idea of making the user learn a simplified version of the alphabet, rather than attempting to understand standard written characters. Still, just about every PDA and smartphone can trace its lineage directly back to the Newton -- including Apple's iPhone, which, like most of its competitors, now accepts input from a keyboard, dispensing with handwriting recognition altogether. Curiously, Newton's handwriting-recognition technology was ultimately ported to Mac OS X, where it's known as "Inkwell." It hasn't really taken off there, either.
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