You will be filled with drunkenness and sorrow means Oholibah will drink so much of the contents of the cup that she will become very drunk and she will become very sad. Good News Translation says “It will make you miserable and drunk.”

A cup of horror and desolation, is the cup of your sister Samaria: God’s judgment will destroy Oholibah (that is, Jerusalem) completely just as he had destroyed Samaria. The Hebrew words for horror and desolation (see 6.14) have almost the same meaning, so they may be combined by saying “horrible devastation.” Another possible rendering is “complete and terrible destruction and ruin.” Even though this is a poetic passage, translators may need to change the order of these two lines, as in “That cup of your sister Samaria is a cup of horrible devastation [or, destruction].”

Quoted with permission from Gross, Carl & Stine, Philip C. A Handbook on Ezekiel. (UBS Helps for Translators). Miami: UBS, 2016. For this and other handbooks for translators see here .