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My dad was sharing music on 10 inch tape reels long before the walkman, and the walkman itself was far from the first cassette player.

True.. it was not the first. But it was I believe the first portable one that was capable of playing an entire cassette tape from beginning to end. It was the new generation rare earth magnets that enabled this.

If I recall correctly, when you used both headphone jacks, the volume would get weaker.

And Bluetooth doesn't support two listeners! :(

Android supports multiple output for A2DP devices