Winamp — Windows 98 Simulator
Winamp, released in 1997, was the way a whole generation played MP3s on Windows 98. It was tiny, skinnable, had a 10-band equalizer and a playlist editor, and its slogan "It really whips the llama’s ass" came from the demo sound that greeted every user.
Winamp 2 with the classic base skin — main window, graphic equalizer and playlist editor — running on a Windows 98 desktop.
Open your own MP3 files: they are copied into My Documents in the browser, so the playlist is still there next time.