In a previous post I argued that Psalm 23 should be read as a corporate song expressing the hope Israel has in their God as a Good Shepherd. The song is laced with messianic hope for a future true Shepherd who will lead them out of the “valley of the shadow of death” to the House of the Lord, where they will live forever. As I stated previously, the two metaphors (God as shepherd and God as host) are common metaphors expressing messianic hope in the Hebrew Bible and they are often paired (Ezekiel 34 and Isa 40-55, for example).
The presence of the Shepherd is a comfort to the flock. Unlike Psalm 22, the worshiper feels the presence of God in a very real way and he is comforted by this. While it is true that “to comfort does not mean to sympathize but to encourage,” (HALOT, 689, citing Elliger), the word has a very tender and compassionate undertone. It is often associated with comforting someone after the death of a loved one. The word is used in Gen 37:35 to describe the effort of the family to comfort Jacob after Joseph appears to have been killed (cf. Jer 16:17).
The word appears in several Messianic contexts. In Isa 61:2 the activities of the “anointed one” includes comforting those who mourn. This is the text Jesus read in Nazareth at the beginning of this ministry, directly applying it to himself as the Messiah, the good Shepherd who will comfort the one who mourns. In Isa 66:13, when Jerusalem is restored, she will be comforted by the Lord as a mother comforts her child.
There are a number of texts which describe God as tenderly comforting Israel (Isa 1:21; Ps 71:21 86:17 119:82; God comforts his people Isa 49:13, 52:9, 66:13, God comforts Zion, Isa 51:3; Zech 1:17; Isa 51:12 Jer 31:13, Lam 2:13; Ps 119:76, with hesed). Perhaps most significant for the argument I am making here is Jer 31:13 which describes the future time when God makes a New Covenant with his people. “Then shall the young women rejoice in the dance, and the young men and the old shall be merry. I will turn their mourning into joy; I will comfort them, and give them gladness for sorrow.” The future age will be characterized by a reversal of Israel’s mourning (Lam 2:13). Instead she will rejoice as the Lord tenderly comforts her.
Verse five has three metaphors which are usually found in the context of the Messiah elsewhere in the Hebrew Bible. 
Preparing a Table – Messianic Banquet. This is a banquet eaten in the presence of the enemy. This may be a result of a treaty (the enemy is invited to eat with the King who conquered them), or more likely the table is spread on the field of battle and the enemy is destroyed. To “spread a table” implies a sumptuous meal. While the word table can refer to any meal, it is used for a king’s banquet (Judg 1:7 1Sam 20:29, 34, 2Sam 9:7,10, 11, 13; 19:29 1Kings 2:7, 5:7 10:5 / 2 Chron 9:4; Dan 11:27; Neh 5:17), this does not have to be a table, but rugs spread out on the ground for a king to eat a banquet, as Isa 21:5. The term is used of an eschatological banquet in Isa 65:11, the Lord sets a table for Fortune, and in Ps 78:19 it refers to God setting a table in the wilderness, in Prov 9:2 Lady Wisdom has prepared a table.)
Anointing with Oil – Messiah. This is not the word typically used for anointed which becomes the title Messiah. The verb דשן in the piel has the connotation of refreshment or enrichment. But since the object is the psalmist’s head, and oil is used to “refresh his head,” anointing with oil seems to be the meaning. It is used in another messianic text, Psalm 45:7. The cognate noun is used to describe foods at the eschatological banquet, they are “fatty” (Isa 55:2, Jer 31:4, cf. Ps 36:9, 63:6, 65:12 for rich, abundant foods). This word is also a connection between the end of Psalm 22 and Psalm 23. Psalm 22:30 may use a rare form of this verb meaning “grow fat.”
Overflowing Cup – The banquet described is abundant, the worshiper’s cup (goblet) of wine is never empty, it overflows. The word is rare in the Hebrew Bible, but in cognate languages the verb has the idea of satisfaction of appetite and even drunkenness, but also irrigation, springs, a good water supply.
The psalm began with an affirmation of faith in the gracious provision of the Lord even in the midst of suffering, but it ends with a future hope that the Lord’s people will dwell in his presence forever.
Despite the fact that we tend to personalize Psalm 23, read in the context of the Hebrew Bible, it is likely that God as Shepherd implies Israel as sheep. As the nation passes through the valley of the shadow of death, they need not be afraid since the Lord defends them and will comfort them when they suffer.