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The "lamp" of the wicked seems to be their life (cf. Proverbs 13:9 b) or, more particularly, their conscience (cf. Proverbs 20:27). If this is so, the verse is saying that arrogance and pride are the sum and substance of the life of the wicked, and that these are sin.
This proverb makes sense if we keep in mind that roofs in the ancient Near East were flat and people used them as patios. It is better to live alone outside, exposed to the elements, than in the sheltered, comfortable interior of one’s house if one has to share the inside with a scolding woman. Spartan conditions with peace are better than physical comforts with strife.
"Rest" is the poetic equivalent of "dwell." [Note: Ibid., p. 404.]
A ransom is a payment given to free a person from some penalty he has incurred, similar to posting bail to get out of jail. In this case, it appears that God punishes the wicked, and in doing so He sets the righteous free. Such would be the case if the wicked were oppressing the righteous (cf. Proverbs 11:8). God delivers the righteous by punishing the wicked who oppress them.
The contrast is between the person who listens to falsehood and repeats it, and the person who listens to the truth and repeats it. The first person has little concern for listening carefully, but the second person listens, learns, and applies. Heeding the truth makes all the difference.
"The key phrase is a man who hears: his first aim is to know and understand, not to grind some axe. . . . the man who listens (Isaiah 50:4) is the man worth listening to." [Note: Kidner, p. 146.]
Ross believed that the verse teaches that "false witnesses will be discredited and destroyed." [Note: Ross, p. 1058. Cf. McKane, p. 556.]
A wicked man puts up a show of confidence, but it is a bluff. His bold face reflects a hard heart that holds the opinions and views of others in contempt. [Note: Plaut, p. 224.] The upright, on the other hand, does not need to pretend to be something he is not because he is walking on the right path.
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Constable, Thomas. DD. "Commentary on Proverbs 21". "Dr. Constable's Expository Notes". https://studylight.org/
the Week of Proper 14 / Ordinary 19