Way back in the mists of time, recordable media came on spools and were hand-threaded through the works of the device. Mistakes were nasty - 100 meters of 1/4 inch tape on the floor takes a LONG time to wind up again (Very easy to do - change from fast-wind to play without slowing the reels down. Inertia will handle the rest).
The self-contained cassette was a major leap forward. This end in first, push down at the other end, press Play. Now, how to we get it out? Well, it went in by pushing it down so it seems reasonable to push the Up button to get it out.
Almost all the early cassette drives were top loaders. It was mechanically a lot simpler to design a tray that used finger power to push the cassette over the various bits than to have the machine do it. Front loaders were the next "wow" product - we can stack things!! But it was still very obvious that the cassette went down into the mechanism - you could see the thing drop, especially on home VHS players. Thus the "Up" symbol still made sense.
Today it's like the floppy disk icon meaning Save. I haven't seen a top-loading media drive (or a floppy disk) in over a decade, I have friends young enough to have never seen one. It's just always been that same icon.
Other icons in the same category are the brake icon in your car - it represents a drum brake mechanism which most drivers today don't have and even fewer have ever seen (they're nasty to work on).
The disk drive icon is going the same way - spinning drives do look like the icon but as SSD become standard the storage device will change to just another circuit card with no distinctive form. The icon will remain.