Beginning in the mid-80s, Calderon began working in guest spots on such TV series as "Miami Vice", "The Equalizer", "Law & Order" and "New York Undercover", often as either hoods or cops. He was a regular cast member on the gritty, short-lived "Dream Street" (NBC, 1989), and was cast as a detective in "The Wright Verdicts" (CBS, 1995). His TV-movie debut was as a villager in "Ernest Hemingway's 'The Old Man and the Sea'" (NBC, 1990), and he went on to play supporting roles in "The Keys" (NBC, 1992) and the busted pilot "Dark Angel" (Fox, 1996), as a New Orleans police chief. MTV viewers also saw him in Michael Jackson's "Bad" video.
Calderon's film career began slowly with small roles in the low-budget actioners "Game of Survival" (1985) and "Band of the Hand" (1986). The character names of his next few roles indicate the kind of typecasting Calderon endured: Speed in "Sticky Fingers" (1988), Pizza in "The Chair" (also 1988) and Juan in "Penn and Teller Get Killed" (1989).
Finally, a good role in the noir thriller "Sea of Love" (1989) brought Calderon to the attention of casting directors and he has rarely been idle since. He brought his tough New York, slightly ethnic persona to supporting roles in Abel Ferrara's "King of New York" and as a stoolie in Sidney Lumet's dark "Q&A" (both 1990), as a cop in Ferrara's "Bad Lieutenant" (1992), "The Firm" and "Lottoland" (both 1993), and Quentin Tarantino's "Pulp Fiction" (1994). 1995 was a very busy year for Calderon: he appeared in Spike Lee's "Clockers", was the demented Lili Taylor's professor in Abel Ferrara's "The Addiction" and had a turn in the Tarantino-directed segment of the unfortunate comedy "Four Rooms". That same year, he also played two addict roles, a crack-head in "Sweet Nothing", alongside Michael Imperioli and Mira Sorvino, and a coke-head in "Condition Red".