When has Ponyboy seen Darry cry in S.E. Hinton's The Outsiders?
In Chapter Six of S.E. Hinton’s novel The Outsiders, Dallas has retrieved Johnny and Ponyboy from their hiding place following the killing of the Soc. On their way back to town, the boys see a church on fire and stop to help. Johnny is badly injured while saving children trapped by the fire, but Ponyboy survives with minor injuries. It is in this context that Ponyboy describes his oldest brother, Darrel, responding emotionally to the events that could have killed Ponyboy. The following passage from Hinton’s novel is located on page 84 of the electronic version of the text used for this answer, the link to which is provided below:
“ let go of Soda and stood there for a minute. Darry didn't like me... he had driven me away that night... he had hit me... Darry hollered at me all the time... he didn't give a hang about me.... Suddenly I realized, horrified, that Darry was crying. He didn't make a sound, but tears were running down his cheeks. I hadn't seen him cry in years, not even when Mom and Dad had been killed.”
Darrel and Sodapop, the middle of the three brothers, are older and more hardened to their way of life, especially the former. They have led a difficult life, orphaned and financially destitute, with the ever-present threat of being separated and taken away by social workers. The bond between the brothers, never doubted, is reaffirmed following Ponyboy’s experience with the fire – an event that would take Johnny’s life.