YouTube doesn't belong on the list. The process you're describing is fully legal under the DMCA and has been the operating mode for every site that allows user submissions.
Having used the web in 1995 with a 56k modem, I find the idea of a period-appropriate "YouTube" somewhat amusing. I'm not even sure RealPlayer did video that early.
RealAudio was released in April 1995. If you listened to RealAudio files (files, because most modems couldn't stream them real-time), the quality was terrible though.
I remember the very first MP3 I ever downloaded was a 3:50 song, about 4MB, and took about 2 hours to download. It actually took 2 days of wall-clock time, because my parents kept kicking me off the phone (thank goodness for ZMODEM). And then I found out that my computer (Mac Centris 660AV) was too slow to play it back real-time, so I set about decompressing it. And since it was a 40MB file and I didn't have 40MB space lying around (the whole hard disk was only 230MB), I set about backing up files to ZIP disk until I could. After about a week I finally had my audio file ready, and the experience was magical: near CD quality audio downloaded off the Internet.
