> modern equivalent of the classic WinAmp that runs on Windows

WACUP — originally Win Amp Community Update Project, although they have distanced themselves from any mention of the original for legal reasons. It's literally Winamp, and it rules: https://getwacup.com/

Get the 32-bit version for now if you want to use the “Modern” (Winamp 3 & 5) skinning engine that has not yet been ported to the 64-bit ver. Worth it because I really really love the “Classic Modern” theme it includes: https://www.deviantart.com/victhor/art/Winamp-Classic-Modern...

Here it is on Windows 11 on my Framework 12 :D https://i.imgur.com/teYadOi.jpeg

> modern equivalent of the classic WinAmp that runs on Linux

Probably Audacious. Its modern defaults don't look very Winamp-ish, but it's a descendant of XMMS (a straight-up WinAmp clone from back in the '90s) by way of Beep-Media-Player: https://audacious-media-player.org/

> modern equivalent of the classic WinAmp that runs on macOS

No idea :)

For Windows & Mac, you can do foobar2000.

For MacOS, you can use Vox, https://vox.rocks/mac-music-player

I personally use MPD (or something like moodeAudio), and then use clients to listen on various platforms.

Foobar2000, but I'd recommend hosting something like Navidrome and using a browser for playback these days depending on your setup / household

Rather than using a browser for playback, I would recommend Supersonic or some other player that can speak the Subsonic protocol that Navidrome supports. Desktop apps will be a much more pleasant experience than a browser.

Strawberry can do this and was already my favorite music player on Linux/BSD systems even without that: https://www.strawberrymusicplayer.org/#features

It's a maintained Qt6 fork of Clementine, which was a port of the amazing Amarok 1.4 to Qt4, which is all that Amarok 2 should have been in the first place.