For years Winamp was simply unrivalled in terms of its vast plugin support. I know foobar2000 has certainly been catching up in recent years, but I wouldn't say I'm willing to dump Winamp entirely in favour of it.
It's because of the plugins that I really don't see the likes of VLC as viable replacements. Here's hoping ArchiveTeam is busy preserving all of Winamp.com as we speak.
BTW, current rumours are that
Microsoft is showing some interest in acquiring Winamp and Shoutcast from AOL. Personally though I feel it may be
better off as open-source.