Young Michelangelo Buonarroti’s experience was deeply marked by his cult of Antiquity, reverberated in the creation of artworks such as the Sleeping Cupid and the Bacchus and shared with Raffaele Riario and Jacopo Galli, his patrons during his first stay in Rome (1496-1501). The cardinal-camerlengo Raffaele Riario was an important promoter of the cultural challenge lead by the humanist Giulio Pomponio Leto, founder of the Roman Academy, and his followers: to arouse the glory and the forms of the antique theatre in Christian Rome also through the actual staging of dramas in Latin. Therefore, it is still necessary to re-evaluate the genesis and the essence of Michelangelo’s artworks, which took life from the Ancient and Renaissance literary and philosophical sources cultivated by the artist as also fostered by the Pomponians. It could be also reconsidered, in the historical context of the conflictual condition documented between the cardinal Riario and pope Alexander VI, the so-called “refusal” of the Bacchus caused by the intention to conceal those antiquarian contents of the artwork as they belonged to a sphere which was already judged as subversive and they could then become the suitable excuse to justify the aspire of the Borgias to the cardinal’s properties. We can then understand, this far, that Michelangelo was actively immersed in the reconstructed network of cultural sodalitas connections in the Renaissance Rome, to which he contributed not as a mere executor of admirable works of art, but rather as an all-round intellectual.