Can't Delete Large Files

Just about every time I try to permanently delete a large file or folder, either by shift/delete or emptying the recycle bin the operation hangs up.The little window opens and it counts up the size of the file and that it. Nothing else overtly happens. The status bar never starts indicating and the window just sits there with the little green lights chasing each other across it. If I try to cancel or close the window it nothing happens.During the time all this is going on, I can hit ctrl/alt/del and select Task Manager and it simply goes back to the desktop with this window still squatting there doing it's thing. I have pinned TM to the task bar and tried starting it from there but it never starts. Eventually everything just slows to a stop and nothing works which would seem to indicate some kind of memory leak. There are no error messages during any of this.I have to hit reset and restart the computer that way in order to regain control and we all know how bad an idea this is. I've already had my boot sector eaten once causing me to have to do a total rebuild and I'd prefer not to have to do it again.