Frodo's departure from the Grey Havens, definitely. That or when Sam thought that Frodo was dead after Shelob attacked him and Sam was trying to figure out what he should do.
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Originally Posted by Sir Kohran
Boromir's death. He had so much potential for good and yet he was cut short before his time.
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I think his death is sad, too, but consider it a mercy that the professor killed him when he did and with orcs. Have you ever read the HoME book The Treason of Isengard? In it there is a sort of time line, or lay out of the book, that Tolkien wrote and he was going to have Boromir go on and get worse and worse and eventually get killed by Aragorn... That
would have been tragic.
-- Folwren