When I was growing up, the impression I got is that there was a huge gap in ancient Jewish literature between the last books of the Bible, closing shortly after Cyrus the Great let the Jews return to their homeland in 538 BCE, and the Mishna, the first written formulation of the Oral Torah, written at the start of the third century CE.
This is unfortunate, because the rabbinic Judaism of the Mishna is very different to the ancient Israelite religion depicted in the Bible, and because of a taboo against writing down the Oral Law, there's very little to see how we got from the one to t'other. The Talmud paints a picture that "we've always done things this way", but, as liv first pointed out to me a dozen years and more ago, this is Pharisaic propaganda. The Pharisees radically reformed Judaism, recentring it from the Temple to the synagogue and home, to enable it to survive the destruction of the Temple, but, because they lived in a society that rejected innovation in religion, they had to make out everything new they came up with to have gone back to the year dot, even where the Bible clearly disagrees with it.
But it's not actually true that the literary record between the close of the Bible and the Mishna is as empty as one might think. There's a whole bunch of documents that were written during this period, which the Jews largely went to forget about; we call them the Apocrypha, and the Pseudepigrapha (and the writings of Philo of Alexandria and Josephus, and *ahem* the Gospels). None of these give us an in-depth examination of the development of the Oral Law or the embryogenesis of Pharisaic Judaism, but there are some clues if you look for them.
For example, one of the two main prayers in the Jewish liturgy is the `Amida. The Talmud gives a variety of contradicting accounts of how this prayer originated, over the course of hundreds if not thousands of years. However, if you want hard evidence, look to the Wisdom of Ben Sira, which contains a sequence of prayers following the same themes as the central prayers of the weekday `Amida (though the words are completely different).
A second example: The Bible is clear that מְלָאכָה "work" is forbidden on the Sabbath, but does not give more than a few hints as to what this includes: collecting things in (Ex. 16:26, Numbers 15:32) or transporting them into (Jer. 17:19ff) the public domain, conducting business (Amos 8:5, Neh. 10:31, 13:15. The Talmud uses hermeneutics to derive, from the fact that the order to keep the Sabbath is given immediately in the Torah after the instructions on how to build the Mishkān (Tabernacle), that the activities prohibited on the Sabbath are those that went into the construction of the Mishkān. However, this smacks of post-facto justification to me. If you look in the Book of Jubilees, however, written three and a half centuries before the Mishna, the last chapter gives a list of activities prohibited on the Sabbath. With the exception of sexual intercourse (which probably reflects the mores of the all-male monastic Qumran community), the list pretty much reflects modern Jewish practice, but does not correlate at all with the 39 categories derived by the Talmud.
So, returning to the main subject, I became intrigued to know what exactly there are written in the late- and post-Biblical periods, and when it was written, and here's what I found out:
Titles in green are ones I have read, those in red ones I would like to try and get to read some time; those in orange ones I have read but no longer remember anything of. :-( The collection of works is not a comprehensive list of everything written during this period.
The dates here are not systematic: some date ranges indicate uncertainty as to when the book was written, others that it was written over a period. The dates come, where possible, from books on my shelf, and where not, from Wikipedia.
A few of the dates need a little explanation: Ecclesiastes (קֹהֶלֶת), Wikipedia says, has two different sets of dates proposed for it depending on whether it has Greek influence, about which there is no agreement. And though the primary text of 2 Enoch dates to the first century, this text was tweaked to add Christian and Gnostic references any time up to the seventh century.
Lastly, the impression I get is that the Book of Daniel represents the gathering of a series of stories about its eponymous hero written over the course of centuries. Daniel 10 and 11 describe, as a prophesy and with almost all names removed, the political history of the Greek period of occupation of the Land of Israel, breaking off in the middle of the Hasmonean revolt, from which it is deduced that this is when this part of the book was written. But Ezekiel, writing centuries earlier, and a contemporary of the biblical Daniel (if he existed) makes reference twice to Daniel (or Dan'el: the word is written without the י) as a famously wise man, which I take as evidence for the Daniel stories starting in this own time.
Returning to the original point, the upshot is that the period between the close of the Bible and the Mishna is anything but devoid of Jewish literary representation. This confirms my suspicions, but I did have a few surprises in what I have learned from this little project, which can I suppose be summed up as surprise at how short the period between the close of the Bible and earliest of the works in the Dead Sea Scrolls actually was.
I had thought, a little while ago, that the chronology was: the history in Chronicles ends with the return of the Jews to the Land of Israel, and the last of the prophets wrote within a generation of this; then followed Ezra and Nehemiah, about sixty years after the return. Then I discovered that, though the history in Chronicles only goes up to the return (the end of the book quoting the opening of Ezra), the genealogy of the House of David is given for a further six generations, into the fourth century, so I thought the book must have been edited to add this after the rest of it was written.
But now I discover what's actually the case is that Malachi was writing a full century after the first return from the Babylonian exile; and Ezra and Nehemiah weren't written (according to Wikipedia and the Hertz Chumash—though I'd like to get another look at the Soncino Daniel-Ezra-Nehemiah, which gives different dates IIRC) until after the last generation mentioned in Chronicles (though the men themselves lived a little beforehand).