I've previously expressed my love for the mid-90s PalmPilot. Having a gadget to offload details from my brain was just amazing - I kept a precursor to my blog on it and really fell in love with its Date Book and To Do app.
Cloudpilot is a fun, browser-based emulator for it. You have to download its ROM from PalmDB but then it is ready to go. It is amazing what they got into a 160x160 square - admittedly around the resolution of the gameboy (that was already about 7 years old by then) but with the stylus-based character recognition and ability to synch with your desktop, it was a serious information tool that improved my quality of life.
Iterative user testing was a critical factor for the success of the original Palm Powered handheld. The software designers actually did several prototypes of the entire user interface in HyperCard before writing code.
I do wish I had run into HyperCard when it was a going concern.
Finally, making the rounds is Springboard: the secret history of the first real smartphone, an excellent way to spend half an hour (or less if you watching things sped up...)
(FWIW, which isn't a lot, while I respect how Handspring moved the market, that first Visor seems so ugly to me - that very of the moment iMac-ish transluscent plastic didn't actually show you much of interest, and the square design with those unpleasant side ridges... bleh!)
Anyway, The Talk Show of Daring Fireball had an episode talking with the maker of the documentary
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