In 1989, Benicio starred in the movie License To Kill as the Number 2 henchman of a nasty druglord named Sanchez. His character was called "Dario." This is the first movie that I saw Benicio in, and I think it's one of his most menacing transformations.
Dario was the guy that interrupted Felix Leiter's honeymoon and brought the wrath of James Bond down on Sanchez's head.
He was a class-act creep, but we love him anyway.
Images courtesy of The Benicio Del Toro Zone.