Michelangelo’s previously unrecognised borrowing of Raphael’s figure of Heliodorus from the Vatican Stanze for his composition of Venus and Cupid, forces us to reconsider Raphael’s important role in the development of the figura serpentinata, and to consider Michelangelo’s ‘Raphaelism’. There was a dialectical relationship of influence between the two artists in which the borrowing of form was merely a starting point for each of them in the production of figures with many additional, and indeed at times antithetical, layers of complexity. In addition to the key borrowing of Heliodorus for Venus, the extended cluster of figures including Raphael’s figure of Ananias, from the Acts of the Apostles, and Michelangelo’s Saint Paul, from the Pauline Chapel, which stem from the same root idea, in the form of rapid sketches on two Raphael sheets now in the Ashmolean Museum, are discussed.