Hipsterism foretold by three decades. Right down to the ostentatiously large "retro" headphones. Consider the wretched impractibility of this device, though - unless the needle clamped down hard on the disk, you'd have to keep your arm in a level position.
At least you'd want to wear it so the headphone cord was on the same side.
That's assuming the device works at all, of course; more likely a van drove slowly behind Master Richie, beaming music into his headphones with radio waves, giving him the illustion of having a Walkman 20 years before anyone else.
Is he in the real world, or the "backlot set" on the Rich compound? It's hard to tell.