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1998 — Franklin REX
This PDA brought a new meaning to the word handheld as the REX was the size of a credit card. It didn't have many fancy features, Franklin was content to bring simple PIM functions to the REX.
All models of the REX were designed to sync with personal data on a computer, a good thing as early models had no way to input data on the REX itself. Later models got crude data entry capability, a vast improvement, but still not very convenient. The six month battery life made up for the lack of features on the REX.
The REX took the hardware to new heights, er, small sizes, but was pushed out of the market largely due to the popularity of the Palm PDAs.