Mathew Miller wrote: "I am working on a project of compiling outlandish, crazy, insane, midrashim. Any ideas?"
Yes, there are many Midrashim and Aggadot that "seem" to be outlandish. However, they are anything but outlandish, insane and crazy!
For well over a thousand years, our sages have treated every statement by Chazal with the utmost respect. The Rambam, in the Moreh, addresses the issue of Midrashim that seem very strange. And he is just one of a long line of Chachamim, who addressed this problem.
Bottom line: There are no "outlandish, crazy, insane, midrashim." Rather, there are many statements that require in-depth study to unlock the meaning and significance hidden in these Midrashim.
Rav Moshe Chaim Luzzatto claims that Chazal hid all of their secrets i.e., Kabbalah in the Midrashim and Aggadot.
To learn more about Midrash, a good starting point is the essay by Rabbenu Avraham ben HaRambam that appears in the first volume of the Ein Yaakov, both in English and in Hebrew. And see Simi Peters, Learning to Read Midrash.
To get a good idea of how seemingly obtuse Midrashim and Aggadot can be understood, I strongly recommend Be'er HaGolah by the Maharal, his Chiddushei Aggadot, or any of his works for that matter. The Ein Aya by Rav Kook is also a very accessible source. There is a whole section in the second volume or half of Ma'amrei HaRaya by Rav Kook that is devoted to the very strange Rabba Bar Bar Chana stories. These works are just the tip of a very large iceberg of very serious works whose authors work very hard at explaining Midrashim and Aggadot that are difficult to understand.
One last note: What kind of message do we send our students when we talk about "outlandish, crazy, insane, midrashim"? Is this how we want them to relate to Chazal? Yes, Chazal were people just like us, but they were also responsible for forging the pathways of Torah SheBa'al Peh and Halacha, and they were Tzaddikim who are more than worthy of respect and honor.
Mathew, my mother taught me that if you "play" with fire, you will get burnt. And Torah is definitely fire!
David