Winamp: 29 years of the player that whipped the llama's ass

Today, 21 April 2026, Winamp turns exactly 29 years old, counting from the release of version 0.20a. It was 1997, dial-up internet still screeched through 56k modems, and an 18-year-old called Justin Frankel — who had dropped out of university not long before — decided to build a decent graphical interface for AMP, an MP3 decoder that ran only in the terminal. The result was one of the most downloaded pieces of software in the history of Windows. And the soundtrack to an entire generation of nerds browsing the web with the volume at maximum.

What was Winamp, exactly?

First, the context: in 1997 the CD was still king of physical music, but the MP3 format was starting to circulate in the internet's darker corners. The problem was that playing those files on Windows was a headache. The Windows Media Player of the era was slow, ugly and unstable. Winamp arrived like a fist slammed on the table: fast, light, customisable and with an interface that had personality.

The first version was spartan in the extreme — play, stop, pause and open file. That was it. But it was fast, it worked, and it played MP3s without choking. By July 1998 it had passed 3 million downloads. Think about that: 3 million downloads in the middle of the dial-up era.

The genius (and the chaos) of Justin Frankel

Frankel was 18 when he released Winamp. He was studying at the University of Utah, stopped, went to live in the Arizona desert with his mother, and wrote the player in his bedroom. He founded Nullsoft — a name that is, obviously, a dig at Microsoft — and turned Winamp into $10 shareware in 1998. Monthly revenue reached $100,000, all of it from users who voluntarily paid for the licence. On a product built by one person.

In June 1999, AOL bought Nullsoft for $80 million in shares. Eighty. Million. For a music player made in a teenager's bedroom. It was the height of the dot-com bubble, true, but the number says everything about the impact Winamp already had on the market.

"It really whips the llama's ass"

If you had a computer in the early 2000s, you know that sound. The phrase became Winamp's startup sample and entered internet folklore long before "meme" was an everyday word. The origin is less epic than it sounds: somebody emailed Frankel saying Winamp "whips the llama's ass" — a reference to a song by cult artist Wesley Willis. Frankel found it funny, recorded it as the opening sample, and there it stayed forever.

Every time the player opened, that voice shouted the phrase. The whole house heard it. Your parents had no idea what it meant. You pretended it was completely normal. Those were the early 2000s.

Skins, plugins and a culture of customisation

What really defined Winamp wasn't just the sound — it was being able to change the player's whole face. The skin system let anyone redesign the entire interface using bitmap files. By 2000 there were nearly 3,000 skins available to download. Matrix skins. Star Wars skins. Skins that imitated real Sony hi-fi separates. Skins that looked like spaceships. Winamp became a platform for visual expression that anybody could take part in.

The plugins went further: psychedelic visualisations that synced to the music (who didn't sit staring at Geiss in a darkened bedroom?), mad equalisers, support for exotic formats, integration with online radio via Shoutcast. The community built an entire ecosystem around a music player.

The decline and the AOL curse

With AOL in charge, things started to get complicated. Frankel stayed on at the company, but the relationship was tense — he was the sort of programmer who released the source code for Gnutella (a peer-to-peer protocol) on AOL's own intranet while the company lawyers were asleep. Literally. He put Gnutella out in 2000, AOL ordered it taken down, but it was already too late — the protocol was on the internet and became the basis for networks such as LimeWire and BearShare.

Winamp 3, released in 2002, was a disaster. The complete rewrite left the player slow and unstable. Users went back to Winamp 2. AOL lost focus on the product, Frankel left in 2004, and the player slowly withered. In November 2013, AOL announced it was shutting Winamp down. The news landed like the obituary of an era.

The zombie that refuses to die

The end never quite came. Radionomy bought Winamp in 2014 for an estimated $5 to $10 million — a fraction of the $80 million AOL had paid fifteen years earlier. In 2018, a version 5.8 leaked and was later released officially. In 2022, Winamp 5.9 arrived with Windows 11 support. In 2023, there was an attempt to reinvent the product as a streaming platform with NFTs for artists — received with the coolness it deserved.

In September 2024, the Winamp Group released part of the source code under its own licence, the "Winamp Collaborative License". The reception was lukewarm: the licence was so restrictive that the community didn't consider it genuinely open source. The repository was deleted a few days later, after criticism that it contained third-party proprietary code. Classic.

Why Winamp matters, 29 years on

Winamp wasn't just a music player. It was the first time a lot of people understood that software could have personality. That a program could be fast and beautiful and extensible. That a community could build on top of an open platform. That a teenager with an idea in his bedroom could change how the world listened to music.

Spotify, Apple Music, YouTube Music — all of them are, in some way, spiritual children of Winamp. The idea that listening to music on a computer ought to be a fluid, customisable, enjoyable experience came from there. That equaliser bar pulsing along to the bass of your favourite track at three in the morning on Windows 98 — you can't put a price on that.

Happy birthday, Winamp. It really whips the llama's ass.

If you have fond memories of the player — what was your favourite skin? Tell me in the comments. And if you want more computing history served with nostalgia, have a look at the live BSOD that humiliated Bill Gates here on the blog.