The moment when this flipped for me was the iPhone, because unlike Blackberry or Sidekick, this was a device that was meant for both work and play, and it pushed the design boundaries equally together. And you could clearly tell what was business vs personal.
It all had a sort of gaudy messiness that never appealed to the artists and proto-hipsters, but they were the odd ones.
WinAmp skins, but also skins in desktops (WindowBlinds), wallpapers (DeviantArt), icons, ringtones, etc.
AIM profiles with colors, poems, quotes, and links.
