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Casio WMP-1 MP3 Watch

Heading out the door for a run with your tunes while leaving your smartphone at home is no problem these days—wearables like the the Apple Watch let you stream music from the cloud or sync songs for offline listening. But the late ‘90s was the wild west of digital music players, and before the iPod came along in 2001, companies like Casio were stuffing MP3 players into digital watches like the WMP-1. It had enough storage for maybe half an album, and connecting a pair of wired headphones was your only option, which required an extra accessory to be attached to the side of the already chunky watch to add a headphone jack. How you were supposed to run while wearing this without yanking headphones out of your ears is a mystery to us.