What's the Worst Thing Characters had to Face in Middle Earth?

[littlemanpoet]

What was it that Frodo faced that was worst, for him?

Sam?

Any other character, both in LotR and in any other part of the Legendarium?

What does it say about the character that s/he faced it well or not so well, and so forth?

Feel free to ride this question like the general wave with a wind behind it that if feels like to me....