Books that have this vibe?

Preferably Medieval or Renaissance. No Schopenhauer or pop-philosophy.

Petrarch's Secretum is the closest I've got.

The Auto da Barca do Inferno (1517), a play by the Portuguese Gil Vicente. In it you have a myriad of figures (nobleman, eleventh-year-old, fool, procuress, friar, shoemaker, hanged man, etc.) reflecting on their actions before an angel and Satan, before boarding the boat that takes souls to the flames of hell.

>>24528878
>The Auto da Barca do Inferno
Thanks