clear your winamp, play ONE song (ie so theres only one song in the list) then right the next song you want and select "enque selection", make sure shuffle isnt on when theres only 2 songs or else it will play the same song over and over.
Are you doing this on your playlist window or the media library window? If the former, press Q and it should have the number 1 next to the song time. If the latter, then you need to add the song to the playlist and then enqueue it.
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