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

But we’re dreaming of something better

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.

Compared to streaming, maintaining a local music library today “definitely takes a bit more of a kind of commitment,” says Jeremy Morris, an associate professor at the University of Wisconsin, Madison, who studies the digitization of cultural goods like music. It’s essentially file management, a dedicated act of acquiring, building, syncing, sorting, organizing, and preserving a collection. Of course, for many people, that’s precisely the point. But it means that many apps feel like they skew toward more serious collectors, tinkerers, and home audio enthusiasts. If you’re into pro-audio hardware and sound quality, you might use Audirvana or Roon. If you’re interested in watching movies and TV shows in the same app you listen to music, you might use Plex. For people who live in the command line, there’s CMUS, a delightfully arcane experience, but one I ultimately found too hardcore for everyday use. For those who miss the old iTunes, there’s Swinsian, and for fans of open source, there’s Strawberry, Cog, and Quod Libet. All of these options have their merits, but I can’t say that any of them feel right for me.

I often think about the first time I used the music streaming service Rdio. It had a clean, simple interface that was actually fun to use, and put colorful album art front and center. It looked nothing like other apps of the time, and most importantly, it worked differently, too. There were no files to think about, and I could access my entire collection anywhere, anytime. Anja Nylund Hagen, a researcher at Arts Council Norway who has studied the streaming music industry, says apps like Rdio and Spotify emerged during a “vacuum” of good systems for organizing and distributing digital files during the era of legal and illegal downloading. By moving music to the cloud, streaming solved all the thorny file management issues that had defined the digital music experience until that point. It’s partly “why streaming got such a great foothold in the music industry,” Hagen says. But it also meant we never had to figure out a better way to interact with the MP3s in our music collection.

As a result, listening to the music I keep on my laptop requires a willingness to embrace all the friction and fiddling that streaming services solved — and to be fine with my collection being anchored to one device. “Streaming is great in that sense, right?” says Morris, pointing to the fact that it’s never been easier to access your collection on any device, from any place, in any moment or mood. But “it does that with a whole bunch of conditions attached to it that I’m wary and skeptical of.”

The reality now is that music is just another platform. “People tend to forget that there are big commercial interests in being a platform provider,” says Hagen. The scrappy days of Winamp are gone. And as long as music’s gatekeepers and tastemakers are some of the biggest technology companies in the world, it’s going to be hard for a small, inventive, independent music app — something that puts the “personal” back in “personal collection” — to achieve mainstream success. Using such an app is also an increasingly radical position. Like most apps these days, streaming services collect reams of data on their users’ behavior and use algorithms to nudge them around. “The opposite is not allowing anyone to decide your taste except yourself,” Hagen says.

Although it’s not impossible to visit the past — and it’s unlikely local music libraries will ever truly go away — streaming has undeniably made it harder to go back to the way things were. And for an ever-increasing number of users, there is no “back.” Anyone who grew up in the last decade has a completely different relationship with the concept of a file than those who came of age in the era of the MP3. Morris is already teaching students who’ve been raised on Chromebook and phones, where everything is in the cloud. For them, there’s no Winamp nostalgia, no wistfulness for Limewire. “The idea of a download doesn’t even fully make sense,” he says.

Perhaps, then, this ineffable modern app I’ve been trying to imagine need not even be an app in the traditional sense at all. Both Hagen and Morris point to Bandcamp and Soundcloud as services that are trying to do something different, where the line between download and stream is blurred. “It’s not just a different interface,” says Morris. “It’s a different relationship with artists and music.” With Bandcamp, for example, I can download the music I purchase, or stream it through their respective apps, while ensuring those artists get paid. Soundcloud is reportedly planning a similar feature. It’s not my whole collection, nor quite the Winamp successor I’ve been conjuring in my mind, but it’s a pretty good start — a glimpse at something hopeful, something new.

I know deep down that, in an age of streaming, the demand for stand-alone music apps is niche. But I’ve also been thinking about how building and listening to a personal collection is a conscious choice, a show of support, and a more direct engagement with an artist than the passivity of algorithmic streaming. Perhaps like vinyl or tapes, niche will become part of the allure. “I wonder if we’re ever going to get to a point where the digital download is going to have that kind of cachet,” says Morris, suggesting a world where, for a generation that missed peak MP3, managing your own local library becomes “the hip thing to do.” Maybe they’ll have the same fondness for retrofuturistic Winamp skins.

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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