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• 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.
• 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."