This thesis explores Northern Renaissance painter Judith Leyster as an influential female artist of the seventeenth century. Her contributions to the art world as a citizen of the Dutch Republic are unprecedented and commendable. Two of her most prized works are The Proposition and her Self-Portrait. Both of these works are explored in this thesis to better understand Judith’s role as both a market artist and female artist in a male dominant world. The Proposition, a painting embedded with symbolism and mystery, touches upon gender roles, domesticity, and prostitution. Meanwhile, Judith’s Self-Portrait is understood to be Judith’ personal manifesto. Both paintings shed light on Judith’s character and skill. A true “Leading Star,” Judith not only became a master artist during her lifetime, but she also achieved incredible success despite her gender. Judith remains a mystery to many art historians due to her enigmatic past, but through viewing and analyzing her artwork, she is being rediscovered and reinterpreted. My hope is that Judith continues to interest art historians for years to come. She is undoubtedly a master worth remembering.