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Your Nomad Jukebox or Creative Zen sounded better than any iPod — more formats, zero iTunes, pure PC-forum credibility — and it battled the white earbuds in every comment thread of the 2000s. Then came the wildest ending in the MP3 wars: Creative sued Apple over a music-navigation patent, and Apple paid $100 million to settle.
The flash-memory bricks that freed your MP3s from the desktop. Diamond's Rio PMP300, arriving in September 1998 at $200, was the first MP3 player that actually caught on — deck-of-cards sized, running forever on one AA battery, holding maybe eight or ten songs. No moving parts meant no skips, a revelation after a decade of portable CD players. The RIAA sued to kill it; the courts sided with you instead.
The media player that ran the MP3 era. Winamp's dark little window with the glowing green equalizer, endlessly customizable skins, and the MilkDrop visualizer pulsing to your music was where a generation organized its first ripped-and-downloaded music collection — and yes, it really whipped the llama's ass.