One of the few paintings in Western art to illustrate a Talmudic narrative, "He Cast a Look and Went Mad" deals with the confrontation between tradition and modernity. The work reflects the influence of the Jewish Enlightenment, the Haskalah, on European Jews in the late 18th and 19th centuries. This movement encouraged intellectual and social interaction with non-Jews while it challenged the observance of traditional Jewish ritual sand customs.

The title refers to a Talmudic parable that describes the entry of four sages from the second century C.E.--Ben Azzai, Elisha ben Avuyah, Ben Zoma, and Akiva--into a "Garden." In the story, the "Garden" represents a temptation interpreted as either Paradise or mystical knowledge. Of the four, Ben Azzai is said to have "cast a look and died;" his death is considered saintly. Elisha ben Avuyah, on the other hand, fell under the influence of secular thought and defected from the Jewish faith.

The four central figures in the painting are contemporary analogues of the four sages. They too, have faced Ben Avuyah's dilemma of choosing between faith and secularism. Several of these students have already succumbed to modern thought and Haskalah as evidenced by their clean-shaven faces.