He was born in Puerto Rico 1959. Calderon moved to New York with his family at the age of six, where he grew up on the streets of the Lower East Side and Spanish Harlem. Following some time in college, he enlisted in the United States Army and served overseas as an infantryman. Returning to the States, Calderon set his sights on an acting career. Starting out on the New York stage, he won an Obie Award for his performance in Blade to the Heat at the Public Theatre. His most notable Broadway role was opposite Robert De Niro in Cuba and His Teddy Bear. Calderon also appeared off-Broadway in such plays as Requiem For A Heavyweight and Divine Horsemen, and played Achilles in the New York Shakespeare Festival’s production of Troilus and Cressida in Central Park. He is a founding member of the Touchstone Theatre, the American Folk Theatre and the Labyrinth Theatre Company.

Calderon was originally slated to portray the role of Jules Winnfield in Pulp Fiction; Samuel L. Jackson was subsequently given the role.