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Tear Jerker: It
Georgie, in both the book and movie. It helps that Jonathan Brandis absolutely nailed the role of Georgie's grieving brother, Bill, and was very convincing in all of his scenes, but the bit always brings on the waterworks is when he rallies the other kids to help him. The line delivery for "Help me. Please help me. That thing killed my little brother. Help me," was what really did it.
Why are they crying so far apart ?
Eddie's death in the book.
For anyone who has ever known the feeling of falling out of touch with close childhood friends, the ending takes that Up to Eleven when the protagonists, having defeated It and returned to their homes, begin to forget one another. Especially Mike's last lines in his journal as he feels it all slipping away, and has resigned himself to it.
I loved you guys, you know. I loved you so much.
"...if this was a story it would be the last half-dozen pages or so; get ready to put this one up on the shelf and forget it."
All of the Turtle's lines in the book. It pleads Ben not to blame it for creating their universe, imagine the depths of Despair Event Horizon you would have to sink to think like that. That an act of creation, either literal or metaphorical is unclear, would make you think that the sentients from that creation would spite you for being responsible for making them exist. It implies that its lost any notion that life is beautiful and that everything is only pain and existing is a curse. I for one grew extremely morose when it was found such a once fantastic being has truly died in its extra dimensional zone. This troper wonders about the implications of this in the Dark Tower concerning how often (same? but atleast similar and related concept) Turtle is brought up there in as almost positive light as The Rose
The last confrontation between Mike and Henry. Henry's been It's fall guy for the '58 murders, and It's been whispering in his ears since he was a kid. He's hopelessly insane after years of guilt, abuse, and fear, emotionally and mentally stalled at twelve years old forever. Mike trying to talk him down is the closest thing to genuine fatherly concern that Henry ever got. Doubles as a Crowning Moment of Awesome for Mike for pretty much that entire frockin' chapter.