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In my honest opinion, Winamp's downfall was exactly the fact that it changed so little over the years. A default installation resulted in a dated-looking piece of software. It always was a great media player, but for software to stay relevant, development (especially with regards to UI) needs to constantly be advancing.
Back in the day (Winamp 2), I wrote a plugin that tracked and logged the messages and commands sent between various windows so you could see how various buttons and messages interacted across the app. Could filter the messages based on action too. Released to the dev community as a tool for free.
I then wrote a rating plugin where you could set a rating and tempo per track using global windows hotkeys. Done like this so you could rate your music with a quick keyboard press without winamp being visible. I listened to music a lot while coding - so handy.
Then I wrote a plugin for the play list that integrated with the filter options. Select tempo 5 (fast) for an upbeat day, or 1 for slow morbid stuff, then ratings 4+5 (great and best) and your play list is filtered by only this music. Made it easy to get to your best music based on mood. At the time, I don't recall another music player that could do any of this.
Winamp 3 changed the plugin architecture and I had no time to alter all my plugin (just some of them).
A mate of mine and myself used winamp to run an alternative/goth/metal club in PMB for a while. The plugin made it super easy to set the play list up and get on the dance floor ourselves![]()
So ye - sad day. Was very fond of this player - and good memories. Not used in a while though (getting too old).
Time for an open source player to step up.