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1996 — Toshiba Libretto
Japanese tech giants were often the first to produce highly miniaturized mobile devices, and Toshiba pushed the limits with the Libretto. First introduced in Japan, the Libretto was roughly the size of a VHS cassette (if you remember those), yet packed a full Windows PC in the tiny package.
It used thumb controls on the side of the small screen in place of a mouse and buttons. The tiny keyboard was not conducive to touch-typing, but owners didn't seem to mind as the Libretto sold like hotcakes in Japan.
Toshiba continued to make Libretto models for years, and eventually brought them to sell in the US. The last model was a strange beast introduced in 2010, with two touchscreens arranged in a book format instead of a keyboard.
1996 — Palm (Pilot) PDA
Palm started as a division of US Robotics, and with the introduction of the Palm Pilot, was able to gain its independence. The PDAs from Palm became wildly popular and soon became a household name.
That got Palm in trouble with the Pilot pen company, as the latter sued Palm for using "Pilot". Palm dropped the Pilot name, and products were simply Palm PDAs going forward.
Palm had many features that endured the PDAs to the buying public, not the least of which was the hotsync cradle. Users simply dropped the PDA into the cradle, which was connected to a computer, and all personal data would be synced to both devices.
The PDAs of Palm soon morphed into the Palm Treo, the most successful smartphone of the time. The marriage of PDA functions with the phone turned out to be a marvelous marriage, and the Palm Treo introduced millions to the concept.
1997 — Psion Series 5 handheld
Psion introduced the Series 5 PDA to replace its Series 3 model. The new Psion 5 included an innovative sliding keyboard that came forward to provide stability when the clamshell was opened.
The Series 5 used the ARM710 processor that could run 10 to 20 hours on two AA batteries. It had a touchscreen and dual serial connectors (RS-232 and IR) for connectivity to other Series 5 devices.
Most significantly, the Series 5 ran the EPOC operating system, now known as Symbian. Largely through the efforts by Nokia, Symbian came to be one of the most-used OSes in phones of all times.