For me, the painful-beautiful moment that comes to mind is the very end of RotK, when Frodo looks back at his friends from on the boat and he smiles at them. It's beautiful because he looks just as happy as he did at the beginning of FotR, when he was a young, joyful hobbit "still in love with the Shire". But at the same time it's painful because you know that the only way he can recapture that happiness is to leave everything that once made him happy (the Shire, his friends) behind. You know that he can never be happy like that in his home in the Shire ever again. It's sad knowing how the Ring has destroyed him, beautiful that there is a place where he can find happiness and peace again, but sad that there is only one place and to go there means to leave his friends forever.
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Above all shadows rides the Sun and Stars forever dwell:
I will not say the Day is done, nor bid the Stars farewell.
-- Samwise Gamgee
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