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

But we’re dreaming of something better

Matthew Braga
Debugger
Published in
6 min readMar 30, 2021

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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 MP3s. It’s a familiar, welcome feeling, like visiting an old friend or putting on an old coat. But it’s also a stark reminder of just how much the way we listen to music has changed. Music has never been more portable or programmable, and it’s never been easier to soundtrack every mood and moment in your life with the perfect album, playlist, or song.

But listening to music on a computer today is, for better and for worse, like boarding a time machine to an era past. Two decades after Napster’s peak, apps like Foobar2000, iTunes (now simply called Music), and even Winamp are still some of the most widely used players; functional and utilitarian, they get the job done. But I wouldn’t exactly say I enjoy them. Instead, I yearn for something fresh and new to play the music that I’ve bought — an app as simple as Spotify, but brimming with possibility and the feeling of the future, the way it felt to fire up Winamp in the twilight of the CD.

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Debugger
Debugger

Published in Debugger

Debugger is a former publication from Medium about consumer technology and gadgets. Currently inactive and not taking submissions.

Matthew Braga
Matthew Braga

Written by Matthew Braga

I write features and essays about culture and technology. Featured in Bloomberg Businessweek, The Verge, VICE, BuzzFeed, The Globe and Mail, Hazlitt, and more.

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