Wristwatch? OR spinning beachball?
What type of files are you trying to launch? It might be you don't have a compatible app to play that particular type of file; eg: MPeg2 movie.
May I suggest you do a
SAFE Boot & Repair Permissions to see if that improves things.
Oh another thought is LW is too busy at that time. After opening LW don't do anything with it until it settles down. It will be too busy loading incomplete & shared files. If shared files are not all loaded AND accounted for then you won't be able to launch them.