Song of Songs שיר השירים
The song of love that Rabbi Akiva called «the holy of holies» of the entire Tanakh.
Shir haShirim is a dialogue of lovers: she searches for him through the night city, he calls her out to the fields, they lose and find one another. God's name is never mentioned, and in the Yavne period the sages debated whether it belonged in the canon. Rabbi Akiva ended the argument: «all the writings are holy, but Shir haShirim is the holy of holies».
Tradition reads it as a conversation between God and Israel: the Exodus, Sinai, distance and search, exile and longing. It is therefore read on Pesach, where that history begins.
Read plainly it is great love poetry; read as allegory it is the strongest account of the bond between a people and its Creator, containing closeness, grievance and waiting alike. Many communities recite it before the Sabbath begins.