Twenty-five years ago–this would be the late 90s–MP3 players did exist, but they were big, clunky things with very limited memory. I had something called an RCA Lyra which could hold maybe an hour’s worth of tunes at very low resolution. The thing sounded like an AM radio. But there were plenty of experiments.
The band Sneaker Pimps released a single on a device called the Diamond Rio, which was one of the first (if not THE first) widely available MP3 players. Around the same time, David Bowie—a guy who was always looking ahead—made his Hours album available for download weeks before it was released in stores. It must have taken forever—literally hours—to download the thing in 1999 because many people were still restricted to slow dial-up modems.
It would be another couple of years before things began to resolve with the introduction of iTunes and the iPod.