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Microsoft SPOT Watch (2000's)
In the Mid-2000's Microsoft experimented with a 1-way FM broacast radio data service known as MSN Direct.
Among the devices to use this service were SPOT watches which were made by various manufacturers. The data broadcast by MSN Direct included localized weather service, news, and traffic reports.
Microsoft shut down MSN Direct in January of 2012.
IBM OLED Linux Watch (2001)
In the early 2000's, IBM Research experimented with getting the Linux kernel ported to very small microcontroller devices.
As a proof of concept, IBM built a few Linux watches to demonstrate various technologies, and showed them at various trade expositions. But the design was never commercialized.
LG GD-910 3G Watch Phone (2009)
At CES 2009, LG Electronics demonstrated the GD-910, the first true 3G phone watch with touchscreen and video calling capabilities, bringing Dick Tracy's 2-way TV phone to reality. It runs on its own proprietary OS.
At almost $1000 and with no data capabilities, the GD-910 is more of a novelty than a practical smart device.