Hi, this is jewishfeminist02’s husband. Before weighing in on this, I must mention that my Rebbe (Rav Yitzchak Blau, son of Rav Yosef Blau – mashgiach ruchani of YU) has an extensive shiur called “Does the Talmud Have a Sense of Humor?” A recording and mekoros can be found on YU Torah.
Now, here’s a few of my own:
1) Menachos 99b: Ben Dama thinks he knows all of Torah, and wants to learn Greek philosophy. His brother, R’ Yishmael (already known for advocating work in addition to Torah – see Berachos 35b) tells him “v’higisa bo yomam v’laila.” One of the meforshim says that this means you can learn Greek philosophy during bein hashemashos.
2) Berachos 63a: One must teach his son an easy and clean profession. What is that? “Needlework” ???? ????????. In the context of a machlokes about whether one should engage in a profession or learn full time, suggesting a profession whose shorashim resemble “???” and “?????” is probably a pun.
3) Chagigah 14b: There are lots of serious terutzim and halachos following this one, but it starts off with a pretty funny hava aminah:
They asked Ben Zoma: Can you castrate a dog?
Ben Zoma: In chu”l (the pasuk says only “b’artzechem”)
edited. Nice, thanks!