Recently I had a friend over to whom I offered to audition my DIY PC speaker system. The first thing out of his mouth wasn’t praise for my audio equipment but rather, a question about software: “You still use Winamp?” A bit taken by surprise, the best I could come back with was something along the lines of “Yeah, it’s awesome.”

That exchange kept coming back to me later in the day. “What else would I use?” I wondered.

My interest in music developed decades ago but didn’t really solidify until I got my first computer just before the turn of the century. This was right around the time that CD burners and MP3 sharing exploded in popularity, so it should come as little surprise that one of the first programs I downloaded was Winamp.

Developed by Justin Frankel and Dmitry Boldyrev under the Nullsoft banner in 1997, Winamp is a media player that supports a wide array of audio formats including MP3, AAC, FLAC, WAV and WMA, among others. Early versions of the player – stylized WinAMP as a portmanteau of “Windows” and “AMP” (short for the Advanced Multimedia Products MP3 file playback engine it utilized) – offered rudimentary controls, but by the time version 1.006 launched only a few months later, its iconic GUI really started to take shape.

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Renamed “Winamp,” the program added creature comforts like a color-changing volume slider and a spectrum analyzer. Users also had access to an equalizer to alter frequency responses and a playlist to help you arrange tracks. The GUI, resembling an aftermarket stereo head unit, felt period correct, but the real fun came in customizing the look and feel of the player through skins and plugins.

Skins enabled to alter the visual look of the Winamp GUI. With scripting, they also added functionality to the player. There was an entire community behind Winamp modifications and many quality Winamp skins to choose from, although personally I always preferred the simple look of Winamp Classic.

To this day, the only plugin I ever messed with was the visualization variety. Specifically, Geiss for Winamp creates a light show that "lets you fly through the sound waves of the music you’re listening to." Try it sometime; it is great fun.

Winamp was an immediate hit with early adopters. By mid-1998, the program, which debuted as freeware but shifted to a shareware model after launch, had been downloaded over 3 million times. This attracted the attention of major media brands including AOL, which scooped up Nullsoft in June 1999 for $80 million in stock and continued to operate it as a subsidiary.

Mainstream success soon followed. By June 2000, Winamp had 25 million registered users and only a year later it was seen surpassing the 60 million user mark. It was pretty clear that MP3s were going to be the next big thing in music. And they were... for a while, anyway.

Buying Music

One major problem that the industry faced was how to monetize digital music. There was a complete lack of legitimate avenues to purchase MP3s, and the few that did exist at the time were difficult to use, expensive, and restrictive. Many gravitated to file sharing platforms like Napster and Kazaa to build their digital music collections, stolen or not. Winamp was often the player of choice.

Realizing a void in the market, Apple CEO Steve Jobs commissioned his team to build a portable music player – the iPod. The following year, he reached an agreement with major record labels to sell music through iTunes for $0.99 per song. That was far less revenue than what a full album purchase would bring in, but it ended up being a win-win for both parties.

Consumers loved the flexibility of hand-picking only the tracks they wanted without having to spend hours scouring shady P2P sites that had become overrun with viruses. And at less than a buck each, purchases quickly fell into the impulse category.

Meanwhile, the record industry and artists had finally found a way to make money off digital music. It may not have been as lucrative as the good old days, but it was better than nothing.

In the tech world, however, nothing ever stays the same, and the music industry’s individual track purchasing scheme was no exception. Over the next several years, as smartphones and wireless network technology advanced, on-demand streaming music services like Spotify started to come into favor. Seemingly the Holy Grail of music, today’s streaming services grant unabated access to over 40 million tracks for a small monthly fee.

The Aftermath

With listening moving increasingly away from traditional computers, the popularity of programs like Winamp predictably declined.

In early 2014, AOL offloaded Winamp to Belgian radio aggregator Radionomy. In October 2018, Radionomy CEO Alexandre Saboundjian promised that a new version of the program – Winamp 6 – was coming in 2019, but as of writing, no such version has materialized. In fact, Radionomy no longer exists and has been rebranded as Shoutcast.

A link on the Shoutcast website points to, where a leaked version of Winamp 5.8 is currently offered. Many purists, myself included, prefer earlier versions of Winamp due to their simplicity and lack of bloat. I’m personally using v5.03a, released on March 26, 2004. You can grab this on TechSpot Downloads.

So, why would you still use Winamp? Don’t get me wrong – streaming is great, and I use it daily. But even with 40 million songs on tap, there’s a significant gap between what I want to listen to and what is available on streaming at any given time.

Streaming rights are fluid meaning what is available today might not be there tomorrow. Worse yet, most of the obscure stuff I’m into – early content from the local music scene, recordings from local concerts, albums created by family and friends in bands, and even some great artists that never got a record deal, yet put out an album or two – isn’t on streaming.

Even some world-renowned artists haven’t entirely hopped aboard the streaming bandwagon. For example, Garth Brooks held out on streaming for many years before finally inking a deal with Amazon in 2016. When I’m in the mood for something a bit different that I can't get on streaming, I fire up Winamp and let the good times roll.

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The story of software apps and companies that at one point hit mainstream and were widely used, but are now gone. We cover the most prominent areas of their history, innovations, successes and controversies.