After 23 Years, Winamp Is Still the G.O.A.T. Music Player

But we’re dreaming of something better

Matthew Braga
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Screenshot: Winamp Skin Museum

There was a time when the aesthetics of listening to music on a computer could be bulbous, metallic, even downright alien. Sometimes the software glowed like a sinister stereo from an alternate, more advanced reality. Or it could look gaudy, garish, amateurish in its design. There were always hidden panels, visualizers lurking, more sliders than you’d ever need. If you wanted, you could coax music out of a green man’s bald head.

It seemed to make sense at the time.

This was the era of Winamp and MusicMatch Jukebox, a time in the late ’90s and early 2000s when streaming was mostly an unrealized dream. Some people look back on it with nostalgia for the chaos and playfulness of software design’s past. But that’s not why these old music players have been on my mind.

Lately, I’ve been feeling increasingly guilty about streaming my music. I know how little some of my favorite artists get paid (a tiny fraction of a cent per stream). And so, more than a decade after I abandoned my iPod and deleted all my MP3s, I’ve been building my digital music collection back up. I’ve been ripping old CDs and buying new albums on Bandcamp. For the first time in years, I have a folder on my laptop brimming with FLACs, AACs, and…

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