While in the US Army, Calderón served overseas as an infantryman. After his military discharge, he worked as a trail cutter in the Amazon jungle for a team of anthropologists stationed in the border between Peru and Brazil. Later, he traveled extensively throughout Peru by train and on foot, visiting and living in such places as Iquitos, Cuzco and Puno. When he left South America, he lived in Mexico City for three months, traveling to Tijuana and Mazatlán.
Performing
Returning to the US, Calderón worked as a demolition man, and later as a Latin dance instructor. At the same time he began studying and performing in many Off-Off-Broadway productions as well as Regional Theatre. He got his big break in 1984 in a revival of Miguel Piñero's Short Eyes directed by Kevin Conway at the Second Stage Theatre. In 1995 he won an Obie and an Audelco Award for his performance in Blade to the Heat at the Public Theater. His most notable Broadway role was opposite Robert De Niro in Cuba and His Teddy Bear. He appeared Off-Broadway in such plays as Requiem for a Heavyweight; Two Sisters and a Piano and Dancing on Her Knees, both written by Nilo Cruz; Troilus and Cressida at the Delacorte Theater in Central Park, in the role of Achilles; and Divine Horsemen for the LAByrinth Theater Company, a play which he had written, directed and produced. In the 1980s, Calderón appeared in several TV series. He acted in three episodes of Miami Vice, playing a different character in each. He also appeared in the extended music video of "Bad" by Michael Jackson. Calderón co-wrote Abel Ferrara's 1992 crime drama Bad Lieutenant, starring Harvey Keitel; Calderón also performed in the film. He has had various short stories published in literary journals. His last published story was "Primitive Grace" for the international e-magazine Noir Nation. Calderón was almost cast as Jules Winnfield in the 1994 film Pulp Fiction, since director Quentin Tarantino was so impressed by his audition. The role eventually went to Samuel L. Jackson, but Calderón was given a role as a bartender, Paul, who quips the famous line, "Hey, my name's Paul and this shit's between y'all," to John Travolta's character, Vincent Vega. He has performed in numerous feature films, including King of New York, Sea of Love, The Last Castle, The Firm, Four Rooms, Out of Sight, La Soga, Cop Land, Addiction, and 21 Grams. He has made many guest appearances on television series, including recurring roles on Dream Street, Law & Order and Miami Vice. In 2012, he guest-starred in the Blue Bloods episode "Domestic Disturbance", playing Lieutenant Martin Perez. Calderón worked on two films in 2012: West End, directed by Joe Basille; and Biodegradable, a futuristic film shot in the Dominican Republic with an all Latino cast, directed by Juan Basanta. In 2014, he played Arquimedes, the bodyguard of Enoch "Nucky" Thompson in seven episodes of the fifth season of the HBO series Boardwalk Empire. He played Alejandro, a recurring role on Fear the Walking Dead. Since 2017, he has appeared as Detective Santiago "Jimmy" Robertson on the Amazon TV series, Bosch.
