"Oh, That One Might Plead for a Man With God"
Job reproaches his friends for their treatment of him, calling them "miserable comforters" (Job 16:2 Job 16:2I have heard many such things: miserable comforters are you all.
American King James Version×) or, literally, "comforters of trouble"—people who make matters worse rather than better. If the shoe were on the other foot, he would not act like they are now acting but would try to be a source of encouragement and comfort to them (verses 4-5), in keeping with godly character.
"The phrase shake my head at you indicates a mocking posture (as in Psalms 22:7 Psalms 22:7All they that see me laugh me to scorn: they shoot out the lip, they shake the head, saying,
American King James Version×). However, the word comfort, meaning 'to nod the head sympathetically,' is used in [Job] 2:11 of the friends who came to console him. [Yet they obviously failed in their mission.] In effect, Job is saying: 'Please nod your head with understanding instead of mocking and ridiculing me'" (The Nelson Study Bible, note on 16:4-5).
But they would not. Job sinks back into mourning his condition. Shockingly, he seems to refer to God as his tearing, hating, gnashing adversary or enemy (verse 9), though it is possibly that he is personifying his illness—continuing from the previous verse where he said, "My leanness rises up against me." The Hebrew word for "adversary" here can mean "a narrow or tight place," figuratively meaning trouble or affliction (Strong's Lexicon, No. 6862). Of course, it is clear, as we have seen, that Job thinks God counts him as if an enemy (Job 13:24 Job 13:24Why hide you your face, and hold me for your enemy?
American King James Version×; see also Job 19:11 Job 19:11He has also kindled his wrath against me, and he counts me to him as one of his enemies.
American King James Version×). Interestingly, however, in chapter 18 Bildad seems to think that Job is referring to him and the other two counselors as tearing beasts (and thus Job's enemy referred to here) and retorts that Job is the one tearing himself (see Job 18:3-4 Job 18:3-4  Why are we counted as beasts, and reputed vile in your sight?  He tears himself in his anger: shall the earth be forsaken for you? and shall the rock be removed out of his place?
American King James Version×). It is true that Job saw himself as a fallen man who was being kicked while he was down—seemingly something only enemies would do. It is also conceivable that Job realized that Satan, as the enemy of humanity and God, was particularly his own enemy.
In any case, whoever or whatever Job is labeling as his devastating enemy, there is no question in his mind that his illness and even the torment from his friends is ultimately from God—either directly or because God has allowed it. And this was in fact so. Job is correct in verse 11 when he states: "God has delivered me to the ungodly, and turned me over to the hands of the wicked." For as we know, God had told the very king of the wicked, Satan the devil, "Behold, he is in your hand" (2:6).
Yet by the wicked here, Job probably had particular people in mind—passersby perhaps—who were taunting and even striking him and spitting on him, though he may be using these terms metaphorically for mistreatment (Job 16:10 Job 16:10They have gaped on me with their mouth; they have smitten me on the cheek reproachfully; they have gathered themselves together against me.
American King James Version×; Job 17:6 Job 17:6He has made me also a byword of the people; and aforetime I was as a tabret.
American King James Version×; see also Job 30:1 Job 30:1But now they that are younger than I have me in derision, whose fathers I would have disdained to have set with the dogs of my flock.
American King James Version×, Job 30:9-12 Job 30:9-12  And now am I their song, yes, I am their byword.  They abhor me, they flee far from me, and spare not to spit in my face.  Because he has loosed my cord, and afflicted me, they have also let loose the bridle before me.  On my right hand rise the youth; they push away my feet, and they raise up against me the ways of their destruction.
American King James Version×). Indeed, if metaphorical, it is possible that Job is referring to his friends, classifying them among the wicked.
Job 16:9-11 Job 16:9-11  He tears me in his wrath, who hates me: he gnashes on me with his teeth; my enemy sharpens his eyes on me.
 They have gaped on me with their mouth; they have smitten me on the cheek reproachfully; they have gathered themselves together against me.
 God has delivered me to the ungodly, and turned me over into the hands of the wicked.
American King James Version×seems to also be a foreshadowing of the suffering of Jesus Christ. The words "They gape at me with their mouth" are later used by David in Psalms 22:13 Psalms 22:13They gaped on me with their mouths, as a ravening and a roaring lion.
American King James Version×—this psalm picturing the future suffering of the Messiah. In His time of greatest torment, Jesus finally came to the point where He, like David, cried out, "My God, My God, why have You forsaken Me?" (Psalms 22:1 Psalms 22:1My God, my God, why have you forsaken me? why are you so far from helping me, and from the words of my roaring?
American King James Version×; Matthew 27:46 Matthew 27:46And about the ninth hour Jesus cried with a loud voice, saying, Eli, Eli, lama sabachthani? that is to say, My God, my God, why have you forsaken me?
American King James Version×; Mark 15:34 Mark 15:34And at the ninth hour Jesus cried with a loud voice, saying, Eloi, Eloi, lama sabachthani? which is, being interpreted, My God, my God, why have you forsaken me?
American King James Version×). Christ obviously felt some of what Job was feeling.
"[Job 16] verses 18, 22, and 17:1 indicate that Job thought he would die before he could be vindicated before his peers; so he was concerned that the injustice done to him should never be forgotten. That is what he meant when he called on the earth never to cover his blood or bury his cry (v. 18). In Genesis 4:10-11 Genesis 4:10-11  And he said, What have you done? the voice of your brother's blood cries to me from the ground.
 And now are you cursed from the earth, which has opened her mouth to receive your brother's blood from your hand;
American King James Version×Abel's innocent blood was crying out to God as a witness against Cain. So Job was consoled to think his cry would continue after his death. And there is one in heaven who would listen to it (vv. 19-21)" (The Expositor's Bible Commentary, note on 16:18-17:2).
In Job 16:21 Job 16:21O that one might plead for a man with God, as a man pleads for his neighbor!
American King James Version×, Job longs for someone to intercede for him with God. On one level, this was probably a desire for Job's friends to cease from their accusations and start praying for him. Yet it may also anticipate the role of Jesus Christ, our Intercessor and Advocate (see Hebrews 7:25 Hebrews 7:25Why he is able also to save them to the uttermost that come to God by him, seeing he ever lives to make intercession for them.
American King James Version×; 1 John 2:1 1 John 2:1My little children, these things write I to you, that you sin not. And if any man sin, we have an advocate with the Father, Jesus Christ the righteous:
American King James Version×).
In praying to God in Job 17:3 Job 17:3Lay down now, put me in a surety with you; who is he that will strike hands with me?
American King James Version×, "Job uses the language of ancient business contracts and asks some 'pledge' (down payment) from God as security against the vindication that will surely come. Only God can demonstrate Job's innocence and despite his despair and ambivalence he believes that God will" (The Bible Reader's Companion, note on verses 3-9).
The translation of verses 8-9 is disputed. Some see the meaning as truly righteous people being unhappy with the hypocritical friends—or that they would be if they were made aware of the situation. Yet others see Job as being sarcastic here—speaking of "the innocent" (his friends) stirred up against "the hypocrite" (himself). In context, the latter seems more likely. The Good News Bible paraphrases the passage this way: "Those who claim to be honest are shocked, and they all condemn me as godless. Those who claim to be respectable are more and more convinced that they are right." This flows right into verse 10: "As for all of you, come back and try again! But I will not find a wise man among you" (New Living Translation).
In the Hebrew wording of verses 11-16, it is not clear if Job is entertaining the possibility of hope and realizing the foolishness of wishing for death or if he is belittling the idea of hope and is in fact wishing for the relief death would bring.