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So much nostalgia. The era of Music Match, Winamp, Napster (and friends), 32-128mb mp3 players and CD-R drives. It was magical.
And Foobar2k :D
Still using foobar2000 here. :)
Oh wow, foobar. I forgot that I converted to foobar for a couple of years before streaming music became a thing.

I think I actually listened to a much wider variety of music back then. These days I pretty much listen to the same Spotify playlists.

Still in active development - last release was just under a month ago! There's a mobile version now, too.
Dating myself, but I remember the first time I heard about mp3s. In a school trip, another kid told me that you could download songs in files that were only a megabyte a minute. I was incredulous. Up until then songs were wav files and video was in massive QuickTime files that took decaminutes to download for tiny snippets. Turns out he was right though :)
Remember the first mp3 player you ever saw?

A kid in my middle school had one that ran on a single AAA battery. Mind immediately blown.

Meanwhile I was carrying around a $20 CD player and a packet of CDs.

Interestingly, it looks like Fraunhofer (much to its later regret) released the first real-time MP3 player (didn't have to be decompressed first) in 1995: https://en.wikipedia.org/wiki/WinPlay3 ... the only option until Nullsoft's 'WinAmp' came out in 1997.