I can stream almost any song I can conceive of in a matter of seconds from my phone. In doing so I can play it wirelessly across every speaker in my house simultaneously as well as on my TV. The lyrics will be displayed on that TV alongside animated cover art and I can control playback with my remote. I will have other similar music suggested to me automatically when that song is finished playing. Guests at my home can add music to the queue from their phones without any additional setup or intervention on my part.
You don’t have to want to do any of that yourself, but if you can’t concede that that sort of experience would have been utterly inconceivable in the days of Winamp—while being boringly commonplace today—I’m not sure we can have a productive discussion.
VLC has been able to stream to/from devices since ~2000. It has captioning support but I don't know if that applies to music. I guess WinAmp came out in ~1998 but it added support for shoutcast in ~1999. The size of computer needed to run winamp/stream shoutcast has shrunk I suppose. But anyways it was certainly conceivable as it was already a commercial product 25 years ago.
You don’t have to want to do any of that yourself, but if you can’t concede that that sort of experience would have been utterly inconceivable in the days of Winamp—while being boringly commonplace today—I’m not sure we can have a productive discussion.