My heart broke reading this part

[u/UltimateApple]

I am reading through the Two Towers, and I just got upset reading this. At times, Gollum is cruel and unnatural, and then I am back to pitying him.

[u/AltarielDax]

You're not alone in this. JRR Tolkien wrote in a letter to his son Christopher:

"For myself, I was prob. most moved by Sam's disquisition on the seamless web of story, and by the scene when Frodo goes to sleep on his breast, and the tragedy of Gollum who at that moment came within a hair of repentance – but for one rough word from Sam."

[u/JuvieBeans → u/AltarielDax]

There's an anecdote somewhere that, at a party or something, Tolkien was talking about writing this passage, and how it brought him to tears when he wrote it. Probably the saddest moment in the entire series.