Philermo Fregoso - [Post Incunable] Riso de Democrito: et Pianto de Heraclito - 1515

The Two Masks of Wisdom: The Knight Who Questioned Fate
This Milanese edition of 1515, printed by Zanotto da Castione, offers one of the most complete forms of moral and allegorical meditation that characterizes early Lombard Cinquecento literature. In the short poems dedicated to Democritus's laughter and Heraclitus's tears, Antonio Fileremo Fregoso constructs an inner journey where the contradiction between mocking the world and feeling compassion for its miseries becomes a process of understanding. The two philosophical figures emerge as symbolic polarities of the same truth: the vain instability of humanity. The knight-poet, an aristocratic and disenchanted voice, translates into elegant tercets a universal drama, suspended between Christian morality, skepticism, humanist astrology, and meditation on the fragility of fortune. The work, rare in its edition and fundamental to Lombard poetry of the early Cinquecento, is today a valuable testimony of a moment when literature, ancient wisdom, and modern restlessness sought balance in poetic language.
Market value
There have been no recent specific auction passages for this 1515 edition. Milanese copies of humanistic vulgar works, especially when well-preserved and with wide margins, have seen a strong increase in recent years, with significant awards in specialized sales. The absence of copies on the market increases perceived rarity and allows for a higher valuation compared to contemporary prints with greater circulation.

Physical description and condition
Initials rubricated in red by a later hand. Pages (2); 96 unnumbered; (2); two cards reproduced on antique paper. The paper is in good overall condition, with light browning and wide uncut margins. The binding is in full later parchment. The typographic mark on the title page is clear and well impressed.

Full title and author
Author: Antonio Fileremo Fregoso
Full title: Laughter of Democritus: and Weeping of Heraclitus composed by the magnificent knight Phileremo D. Antonio Fregoso
Printed in Milan for Zanotto from Castione.
1515

Context and Significance
Democritus' 'The Riddle' was first published in 1506 and reprinted in 1507, along with 'The Cry of Heraclitus.' Both poems are written in tercets and belong to a series of allegorical and philosophical works, all very refined examples of humanist poetry, with numerous references to classical culture and inspired, linguistically and stylistically, by the courtly models of Dante and Petrarch; all achieved considerable success, are often reprinted, and translated into French and Spanish. In the first poem, Democritus introduces the author to the beauties of a garden, where he meets Diogenes and Plato, then drinking from the same streams that gush from the breast of a statue, nourishing those 'divine' beings and representing Philosophy. In the second poem, Dianeo leads the author to the philosopher Heraclitus, who feeds on a spring of tears and describes life as a progression of worries that cannot be avoided due to the pleasures of love and the fear of death; the only remedy he allows himself to hope for lies in a few true friendships. Fregoso retired to his villa in Colturano and took on the nickname 'fileremo' (lover of solitude). His name is among the poets mentioned by Ariosto in his 'Orlando Furioso'.

The volume belongs to the most notable testimonies of Lombard philosophical-moral poetry of the early 16th century. The opposition between Democritus, who laughs at the absurdity of the world, and Heraclitus, who laments its fleeting nature, becomes a powerful symbolic device: a theater of the soul in which the reader recognizes their own oscillation between irony and pain, detachment and participation.
Fregoso, educated in the Sforza courts, infuses his tercets with Milanese aristocratic culture, nourished by classical rhetoric, Christian sensibility, moral astrology, and reflection on Fortune.
In esoteric terms, the work can be read as a representation of the two paths of knowledge: the solar path (Democritus, laughter, detachment, intellect) and the lunar path (Heraclitus, tears, intuition, vulnerability). The author moves between them, a chivalrous figure attempting to reunite opposites into a higher form of awareness.

Biography of the Author
Antonio Fileremo Fregoso (c. 1460 – c. 1530), illegitimate son of the noble Spinetta Fregoso and legitimized by the Emperor, grew up in Milanese courts under the protection of Cicco Simonetta. Active throughout his life in Lombard culture, he authored vernacular poems with a strong moral tone, including Riso e Pianto, La Cerva Bianca, and other poetic compositions. He married Fiorbellina di Lodrisio Visconti and spent his final years in the fief of Colturano. His work reflects an aristocratic, introspective sensibility, closely tied to the intellectual climate of the Sforza era.

Printing history and circulation
The 1515 edition of Zanotto da Castione represents one of the earliest known reprints of Riso e del Pianto. Castione, active in Milan during the first two decades of the 16th century, was a printer specializing in vernacular, poetic, and moral texts. His output is now very rare.
The text originally circulated in courtly circles and only after 1510 did it begin to spread more widely, with subsequent reprints and, in the second half of the century, translations into French (1547) and Spanish (1554). Surviving copies of the early editions are scarce and often incomplete; the 1515 print run is considered one of the most difficult to find on the antiquarian market.

BIBLIOGRAPHY AND REFERENCES
Treccani, Biographical Dictionary, entry Fregoso, Antonio Fileremo.
Cards related to the Castionesque editions of 1515 (to be verified with collation).
Studies on Lombard poetry and humanism from the early 16th century
Research on the Democritus-Empedocles tradition in ancient Italian literature.
Milanese historical catalogs of typography by Zanotto da Castione.