Winamp 2.77 standard running on Windows 2000 Professional SP2 has a memory leak when playing local MP3s and is left on "pause". I can 100% repro application leaking memory by merely pressing the pause button and watching the application memory utilisation slowly climb in Task Manager. This is usually not a problem except if left like this for long periods when low virtual memory warnings start to appear.
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BTW - Despite this feature Winamp still really kicks the lamas ass.