Maimonides on Life - Rabbi Dovid Rosenfeld - Chapter 2, Law 7(a) - Torah through Laughter
“One should not be a person of levity and mockery (‘s’chok v’hatail’), nor sad and somber, but cheeful (‘samai’ach’). So too did the Sages say, ‘Mockery and lightheadedness accustom [a person] to lewdness’ (Pirkei Avos 3:17). They likewise commanded that a person not be unrestrained in levity (‘parutz (broken out) bi’s’chok’) nor sad and mournful. Rather he should receive all people with a cheerful countenance.”
The Mishna writes that one who instructs that a Get (bill of divorce) be written for his wife but does not instruct that it be delivered merely means to “play with” (l’sachaik) his wife — i.e., to torment her, dangling an undelivered Get in front of her face (Gittin 6:6). Likewise, the Rambam above quoted the mishna in Pirkei Avos (3:17) that mockery leads to lewdness. Far from harmless joking around, s’chok implies making light of matters which must not be trifled with, of letting down one’s guard and loosening one’s morals to the extent that nothing is taken seriously and far worse breakdowns may follow.
Laughing in the face of serious life issues will get you nowhere; such is a laugh hiding a crying soul.
In a different vein, it’s interesting to note that the Sages generally have a positive view of humor. The Talmud writes that before the great sage Rabba began his lecture, he would crack a joke, the rabbis would laugh, and then he would sit down with awe and reverence and begin his lecture (Pesachim 117a). There’s certainly a place in life for good Jewish humor. Even Torah study should be tempered with good cheer. We must study with an awe of the gravity of the subject matter being discussed — in fact we should be terrified of misunderstanding or making light of G-d’s word. Yet at the same time we should feel an intense joy at the opportunity to fathom G-d’s Torah. And there’s nothing like a little humor to bring out that warm, joyous feeling — allowing us to loosen up and enjoy our studies.
Original article found on Torah.org