This dissertation examines how Michelangelo advanced his artistic and social identities through portraits executed by his closest friends. By placing these portraits within their respective historical contexts, this study sheds light on how Michelangelo controlled his image in a fashion analogous to his patrons. Above all, the portraits of Michelangelo are an extension of his desire remove himself from the traditional social constructs for an artist in order to achieve artistic autonomy. Michelangelo as the patron of portraits has been previously overlooked, which may have been a result of their unusual nature in the context of self-images of artists and Michelangelos relationship with portraiture. Beginning in the second decade of the sixteenth century and until his death in 1564, Michelangelo oversaw the production of his portrait in various media, including drawings, paintings, prints, sculptures, and a portrait medal. The earliest portraits of the artist by Fra Bartolommeo and Guiliano Bugiardini visually connect Michelangelo to the illustrious artistic traditions of Florence. In particular, Bugiardinis portrait represents Michelangelo in a specific garment that has been misunderstood in the modern literature. Twenty years later, Michelangelo asked either Jacopino del Conte or Daniele da Volterra to execute a painted portrait that reinforced Michelangelos conception of his social status as an artist of noble birth. This portrait marks the beginning of a period in which Michelangelo directly participated in the construction of his social identity through painted and engraved portraits, numerous publications addressing Michelangelos artistic theories, and two biographies. Late in his life, Michelangelo turned to Leone Leoni to execute his portrait medal, which aimed to advance both his social and religious aspirations. After the artists death, Daniele da Volterra and Lionardo Buonarroti desperately tried to maintain Michelangelos wishes for his image through a funerary monument that would have been adorned with a bronze bust by Daniele. Like the tomb, Michelangelos image was quickly appropriated by Giorgio Vasari, who used Michelangelo and his appearance as an emblem for both artistic genius and accomplishment.