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Casio Databank (1980s-current)
In the 1980s, Japanese timepeice manufacturer CASIO introduced the Databank, a LCD watch line that continues to be manufactured to this day. Databanks have had many configurations over the years, including calculator watches, but primarily they have been used for limited PDA-type of functions (Appointments, Contact, Calendar) that we see as common features in today's smartphones.
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.