Apple Newton MessagePad (1994)

The Newton PDA had the dubious distinction of being lampooned in Doonesbury, thanks to its less-than-spectacular handwriting recognition. At nearly 1 pound and costing $700, it was too big and pricey for most users, but it paved the way for smaller, simpler devices like the PalmPilot and the iPod. At the time, there was no cooler gadget to be found. For more, see this description and photo of the Newton.