La Generacion de los Cincuenta (The Generation of the Fifties) is a group of artists, educators, and administrators who worked together to educate Puerto Ricans through public programs in the nineteen-fifties. This came at a turning point in Puerto Rican history, as the island had just gained certain freedoms under the United States. La Generacion de los Cincuenta was able to break down social-political barriers, and managed to gain traction and wide notoriety both in Puerto Rico and abroad. Thus, through their combined efforts they not only educated the people of Puerto Rico, but also created their own market. They were widely successful in Puerto Rico and their influence greatly impacted future generations. My paper will address the history of Puerto Rico after U.S. occupation, including the art history that influenced artists from Puerto Rico. I will also address whether La Generacion de los Cincuenta were successful in their goals and if they had a lasting impact on the art market in Puerto Rico.