Just listened to the first lecture by R' Eliezer Brodt of the Seforim blog, in the eTIM series on "Rare Minhagim Books and Controversies". The subject was the book Malmad haTalmidim, by R' Jacob b. Abba Mari Anatoli. He claimed it was the first book of drashot arranged by parsha, but I wondered, what about the She'iltot of R' Ahai Gaon? Surely a Geonic work predates a late 13th century collection of sermons. Or were the She'iltot more theoretical constructs, rather than records of actual sermons?
The book is in the philosophical mode, being a series of moral/ethical essays based on verses from Proverbs. The author was a big fan of Rambam, naturally. Starting around 1300 there was a big backlash against philosophical writers and works; R' Brodt surveyed R' Anatoli's defenders and detractors. The book languished virtually unknown for centuries, until published from manuscript by Mekitzei Nirdamim in 1866, and once more a century later. Recordings should be available for a nominal fee in the near future.
It seems to me that affinity for philosophy among the Torah world has come and gone in waves, perhaps following trends in the outside world. Here we have a Jewish flowering of philosophy, in the same period that the Muslims were experiencing their Golden Age and engaging in philosophical speculation, whether as the Kalam, or as Sufism, or as Alfarabi'an Aristotelian, which affected Maimonides so strongly. As dar al-Islam began to lose ground to the Christians in Spain and the Holy Land, Jewish affinity for philosophy began to fall off as well.
In the Renaissance, as Christendom began to open itself up to philosophy, Judaism experienced another round of philosophical speculation, peaking in the 1500s with figures such as Azariah dei Rossi and David Gans, who wrote books on natural philosophy and history; until the 1600s when some (such as Spinoza) went too far. But it continued underground for a little while, until the Sabbatean revolution, and later the publication of the works of the Ari, replaced it with Kabbalistic theosophy. "Preachers of the Italian Ghetto," ed. Ruderman, surveys a number of 17th-century figures who supported or opposed philosophy, in much the same way as the sources surveyed (many drawn from Marc Saperstein's "Jewish Preaching") by R' Brodt did in the 14th century. Some of the open opponents of philosophy reveal that they themselves knew the philosophical idiom even as they openly reject it, which makes for somewhat entertaining reading, extracting layers of meaning.
And in the modern period, philosophy has made various attempts to rear its head, particularly as kabbalah had gone into abeyance in the Western non-Chasidic world. Mendelssohn and his circle engaged in it, just as their contemporaries in the German and French Enlightenment brought philosophy out of the middle ages (Kant, Leibniz, Hegel, Rousseau, Diderot, etc). With its association with Haskalah, and Haskalah's association with Reform, it went somewhat more underground for a time, before re-emerging in interwar Europe, when many who were to become the post-WW2 Gedolim, went to Berlin to study philosophy and secular culture (Heschel, Soloveitchik, Hutner, possibly Schneerson). It carried forth to become the underlying rationale for much of modern Orthodoxy. But as Kabbalah returns to Western sensibilities, it too is fading away.