Leonardo da Vincis Saint Jerome is an unconventional representation of a religious figure. Renaissance saints were typically endowed with appropriate physical markers such as beauty and grace; however, Jerome is haggard and aged. This paper will endeavor to reveal the importance of Leonardos unusual aesthetic choices as well as illuminate the congruencies between the Saint Jerome and Donatellos Penitent Magdalen. Donatellos sculpture, which features a similarly haggard and elderly Magdalen, represents a critical prototype for Leonardos Saint Jerome. This paper will also argue that these two works are images of the perfect penitent. The saints weathered and emaciated exteriors emphasize their humanity and transform them into emblems of wisdom and redemption. In both the Saint Jerome and the Penitent Magdalen, there is an important message about the beauty, determination, and strength of the human soul.