Calderón 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. He wrote and directed
Master of the Crossroads, based on his own short story; it was premiered at the Bridge Theater in Manhattan, starring
Kate Jackson. He has had various short stories published in literary journals. His last published story was "Primitive Grace" for the international e-magazine
Noir Nation. 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 (who played the film's main character, Darryl). Calderón appeared in
Abel Ferrara's 1992 crime drama
Bad Lieutenant, starring
Harvey Keitel. Calderón was almost cast as Jules Winnfield in the 1994 film
Pulp Fiction, since director
Quentin Tarantino had been impressed by his audition, but the role eventually went to
Samuel L. Jackson, and Calderón was given a role as a bartender, Paul, who speaks the 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,
The 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. (He reprised the role in the 2016
Blue Bloods episode "Back in the Day".) 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 (final) 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. In 2023, he reprised his role from
Out of Sight as Raymond Cruz in the
FX miniseries Justified: City Primeval. In 2025, he reprised his role of Detective Santiago "Jimmy" Robertson in the
Bosch spinoff series
Bosch: Legacy. ==Personal life==