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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.
TikTok and LunaTik watchbands for iPod Nano (2010)
After the 2010-era iPod Nano was introduced, it seemed natural to create a wristband encasement for it to turn the device into a full-blown smartwatch/wrist-mounted media player.
Design firm MNML created the LunaTik and TikTok bands, and through distribution partnerships managed to sell over 350,000 of these.
While the 2010-era Nano is no longer produced, bands from other companies have been created for the current version, although the solutions are not as elegant given that the current generation Nano is rectangular and larger.