Please provide a little bit more info,
do you use any additional Plugins,
are you playing normally or is "shuffle" and or repeat playlist on?
have you queued the files directly in winamp, or through the media library?
does it hang on a specific file? (e.g. have you tried to play the file with whom your pc crashed, just after winamp has started)?
have you looked in Control Panel->Administrative Tools -> Event Viewer
is a Visualization running while you listen to music?
is it a specific file type when winamp hangs (e.g. everytime a flac file is played?)