The history books of the Old Testament begin with Moses’s death and Joshua leading the Israelites into the promised land of Canaan. These books tell how God’s people conquered the land, struggled with obedience, and experienced cycles of faithfulness and rebellion under judges and kings. Key figures include Joshua, the judges like Deborah and Samson, King David, and King Solomon, whose reign led to the kingdom’s division. The northern kingdom of Israel and southern kingdom of Judah eventually fell into exile due to disobedience, but God later allowed the people to return and rebuild Jerusalem and the temple. Throughout, these historical books reveal God’s faithfulness, Israel’s challenges, and the hope for restoration through His promises.
The historical books overlap quite a bit, giving different perspectives and details to the stories.
Joshua: Joshua takes leadership and leads the people into taking Canaan. The people take an oath to remain faithful to God, and Joshua dies. The author was Joshua, presumably with a scribe filling in the last chapter.
Judges: One woman and several men provide the tribes with a moral compass, convicting them of sin and rescuing them from their enemies. Although the author of Judges isn't listed, it's believed to be Samuel, Nathan, and/or Gad.
Ruth: A short story, set during the time of the judges, about a woman from Moab who remains faithful to her Israelite mother-in-law after the deaths of their husbands. Written by Samuel, Nathan, or Gad.
1 and 2 Samuel: Samuel is born and dedicated as Israel's last judge. He anoints Saul as king, and Saul is succeeded by David. David weathers war, sin, and political intrigue until his death. Tradition states that Samuel, Nathan, and/or Gad wrote the books.
1 and 2 Kings: The first half of 1 Kings describes Solomon's kingdom; the rest of 1 Kings covers a succession of kings in Israel and Judah—some good, most bad. Second Kings continues the narrative until chapter 17, when the northern kingdom was taken into exile by Assyria. Judah is taken into exile by Babylon by the end of the book. It's believed Jeremiah, who served as prophet during the end of 2 Kings, wrote the books.
1 and 2 Chronicles: First Chronicles begins with genealogies up to the establishment of the twelve tribes, then briefly mentions King Saul before going into more detail on David's reign. It ends with his death and Solomon's ascension. Second Chronicles covers Solomon's accomplishments before listing the highlights of the kings of Judah. Ezra compiled the books of 1 and 2 Chronicles using a variety of sources, including the lost document "The Book of the Kings of Judah and Israel."
Ezra: Ezra records the decree of Cyrus that allowed the Jews to return and then lists the families who did return. The temple is rebuilt, and Jerusalem experiences a spiritual and moral revival. The book was written by Ezra.
Nehemiah: With Nehemiah's encouragement, the people of Jerusalem rebuild the wall around Jerusalem, read the Law, repent, and renew their commitment to God. The book ends with administrative details and enforcements of the Law.
Esther: Like Ruth, Esther is a short story which occurred within the context of larger books. In this case, it is of a Jewish girl, still living in exile, who is chosen by King Ahasuerus (Xerxes) to be his wife. God leads her to use her position to save the Jews. It's believed to have been written by Esther's cousin, Mordecai.
The Jewish Scriptures deviate from the Old Testament here in organization. The Neviim, or "Prophets," consist of Joshua, Judges, the Books of Samuel (1 Samuel–2 Kings), the Books of Kings (1 and 2 Chronicles), Isaiah, Jeremiah, Ezekiel, and the twelve minor prophets combined into one scroll. Esther, Ruth, Daniel, and Ezra–Nehemiah are included in the Ketuvim (Writings). In some variations, Ruth was appended to the end of Judges.
There are some issues with continuity between 2 Samuel–2 Kings vs. 1 and 2 Chronicles, mostly when it comes to numbers—like the headcounts of soldiers or the ages of different kings. Some can be attributed to copyist errors; none have any bearing on theological matters. You can find explanations at the CARM.org site.