An Ode to Winamp

On the improbable connections among the old-school MP3 player, Mandy Moore, and the hippest streaming music service

Winamp 2 (Wikimedia)

AOL will officially shut down Winamp on Friday, and I’m sad about it.

It’s not just because Winamp (with an assist from Mandy Moore) set me on the path that led me to become head of design at the streaming music service Rdio. It’s also because Winamp was a key part of what it was like to come of age right at the end of the millennium (and first tech bubble).

In 2000, I graduated from high school and used the gift money to buy my first personal computer. I bought my first car, a Honda Civic. My shitty rock band recorded and released its first (and final) studio album. What would become my professional career also began: I wrote my first line of HTML, built my first website, downloaded my first MP3 from Napster, and fell in love for the first time with a software application. That would be Winamp, of course.

From the second you opened it, you knew Winamp was something different. A booming (ironic) voice would say, “Winamp, it really whips the llama’s ass.”

And it really did.

In 2000, most Windows and third-party applications felt impenetrable, but Winamp felt real. It had soul. I remember thinking, “Whoever made this has to be a musician.” More specifically, they had to be a guitar player. It looked like my Rat distortion pedal or Boss DD-3. I wanted to turn every knob, press every button. My digital music collection was a junkyard of random MP3s and ripped CDs, but Winamp whipped it into something that made sense.

In 2000, most of the websites I designed resembled brochures or posters or gift cards — digital approximations of the era’s conventions. Simple navigation through predictable sitemaps. Home, About, News, Contact. Javascript, specifically, AJAX, hadn’t yet brought the Internet to life. One page would load. You’d “CLICK HERE.” The next page would load. Websites weren’t used, they were visited. So I created glossy onscreen brochures and business cards embossed with rollovers. That was about as interactive as things got, especially if you skipped the Flash intro.

The more I used Winamp, though, the more interested I became in its design. When I found a message board full of custom Winamp skins, I realized that anyone who could create graphics could create a skin. It lit a fire.

That fire kindled into a Winamp skin celebrating my then-celebrity crush: Mandy Moore. If my muse was lackluster, the work was anything but. I was solving problems and thinking about users, not visitors. Each pixel had power. Every icon had purpose. Form and function blurred together in wonderful, wholesome harmony. Designing websites felt like something I had inherited or borrowed from the Print Generation. This, however, was mine. Winamp was teaching me product design.

I guess it was only natural that I wound up designing products that play music. The other day, I fired up some Mandy Moore for old time’s sake. Then I searched every hard drive, every backup, every corner of my tiny digital empire, trying to find the PSD for that skin. I couldn’t. But then, I didn’t really need to, because I’m still designing that same skin more than a decade later. Only this time, it’s for Rdio.

Goodbye and godspeed, Winamp. You will be missed.