Focusing on artists Frida Kahlo and Guillermo Gomez-Pefia, my thesis concerns borders of all kinds: between nations and cultures, between varying artworks, context, and audiences, and between myth and reality. These border relationships are subject to constant evolution and negotiation, and I chose Kahlo's paintings and Gomez-Pefia's performance work to illustrate how two artists have portrayed border relationships across the twentieth and twenty-first centuries in Mexico and the United States, because both artists draw upon borders to hash out shifting personal, political, and cultural identities. Frida Kahlo's nationalist politics led her to portray the Mexican-U.S. border as a force of antagonism. In her modern context, this border starkly indicated a divide between colonial ambitions and domination, between the First and Third world paradigms of her time. Kahlo's consistent technique of self-portraiture led Germaine Greer to declare her "the first ever true performance artist," and in many ways Kahlo's work and life foreshadows contemporary questions of hybridity and pluralism brought to light by Guillermo Gomez-Pefia decades later. Gomez-Pefia's more direct performance pieces question dualistic borders by breaking boundaries and envisioning a borderless world, where boundaries are created and blurred organically rather than dictated by social or political elites. Like Kahlo, Gomez-Pefia's work is highly political, and his indictment of America's negative and dangerous images of Mexico and Mexican immigrants is particularly fierce. Both artists have produced impressive, controversial work that is dense and often difficult to understand, but it is also work that forces audiences to question the status quo and the boundaries we frequently take for granted.