A recent scholarship has extensively documented that music and dance occupied a fraught position in early modern England. This chapter considers works featuring Cupid that hitherto have escaped significant musicological analysis: Robert White's Cupid's Banishment and Thomas Jordan's Cupid His Coronation. In these two masques humanistic discourses surrounding Cupid, music, and dance dovetail with the corporeal realities of singing and dancing bodies in fascinating ways that had the potential to undermine the moralistic purpose of these pedagogical works. Cupid's Banishment, written by the school master Robert White and performed by his students before Queen Anna at Greenwich, draws upon the conventions of the English court masque to portray the triumph of chastity over erotic love. As scholars have noted, White's plot, chastity's triumph over Cupid echoes themes found in Cesare Ripa's Iconologia, a frequent source book for imagery in Jacobean and Caroline era masques.