The brother of another painter known as Scheggia, Massacio was born at San Giovanni Valdarno and lived in Florence in the Popolo di San Niccolò Oltrarno.
He brought extraordinary innovations to early fifteenth-century Florentine art, first among them perspective. His work was studied and admired by Leonardo, who in the Codex Atlanticus (around 1490) praised him as the painter who showed «with perfect work how those who took for author anything other than nature, the master of masters, laboured in vain».
In Florence can be seen his frescoes in the Brancacci Chapel in Santa Maria del Carmine, the Trinity in Santa Maria Novella, and the Saint Anne Metterza formerly in the church of Sant’Ambrogio, now in the Uffizi. Notable is the Triptych of San Giovenale representing the Virgin and Child Enthroned with two Angels in the Pieve di San Pietro a Cascia, near Reggello.