Tear Jerker / The Iliad

• Achilles receiving news of Patroclus's death in Book 18. When Antilochus brings him the news, Achilles throws himself upon the ground and wails loudly; tearing at his hair and dropping dirt upon his own head. It gets to the point that Antilochus starts holding Achilles’s hands because he’s scared Achilles will go for his knife and slit his own throat.
  Achilles: “To this cureless grief, Not even the Thunderer's favour brings relief. Patroclus—Ah!—say, goddess, can I boast A pleasure now? revenge itself is lost; Patroclus, loved of all my martial train, Beyond mankind, beyond myself is slain! Lost are those arms the gods themselves bestow'd On Peleus; Hector bears the glorious load. Cursed be that day, when all the powers above Thy charms submitted to a mortal love: O hadst thou still, a sister of the main, Pursued the pleasures of the watery reign: And happier Peleus, less ambitious, led A mortal beauty to his equal bed! Ere the sad fruit of thy unhappy womb Had caused such sorrows past, and woes to come. For soon, alas! that wretched offspring slain, New woes, new sorrows, shall create again. 'Tis not in fate the alternate now to give; Patroclus dead, Achilles hates to live. Let me revenge it on proud Hector's heart, Let his last spirit smoke upon my dart; On these conditions will I breathe: till then, I blush to walk among the race of men.”
• Hector’s death in Book 22. After Achilles deals him a mortal wound, Hector doesn’t beg for his life. Rather, he begs Achilles to not leave his body out for the vultures and dogs, but to allow his family to take his body so he can have funeral rites. Achilles denies him this request, and he further tells Hector that there is no ransom large enough that Priam could pay for Achilles to spare his corpse. Then after Hector dies, Achilles ties his body to the back of his chariot and proceeds to drag his body around the walls of Troy for Hector’s family and all the Trojans to see.
• While sleep-deprived and in shock after Patroclus's death, Achilles is visited by his ghost in Book 23. He tries to hug it and finds he can't.
• Everything involving Priam, starting with the death of his sons.
  • In particular, going to the Greek camp alone in the dark to beg Achilles for the body of Hector in Book 24. "I have endured what no one on earth has ever done before — I put my lips to the hands of the man who killed my son."
• Helen speaking to Hector's corpse:
  Helen: Hector, dearest to me of all my husband's brothers! These tears of sorrow that I shed are both for you and for my miserable self. No one is left, in all of Troy, that is gentle or kind to me.