I shed a few tears in DTIV and DTVII when:

Susan and Jake died

I cried and sobbed painfully hard in DTVII when:

Eddie died. It was so horrible that it was not a quick death and that he suffered greatly before he passed on. I also cried hard at Oy's death and of course when the book ended and I realized Roland had been on his quest over and over again and he would have to experience all the pain all over again. My heart ached for him.