How do I put files on the Winamp playlist?
If your playlist isn’t already displayed, click the “PL” button to display it. Then on the Playlist window either click the +FILE button and add the files one at a time or click the +DIR button (click +FILE and then slide up) to add a whole directory (and optionally its subdirectories) at a time. To start a new list, click the Load List button, and slide up to New List.