When he was in high school, he became more interested in psychology, and he was an above average student, becoming able to attend college, where he pursued a career as a psychologist.
In 1971, Caballero made his film debut, acting in an Italian-Spaniard-French production, Il Corsaro Nero ("Black Pirate").
That soap opera was the first of seventeen soap operas produced by Radio Caracas Television that Caballero would participate in, including 1983's Leonela, 1987's La Intrusa ("The Intruder") and Mi Amada Beatriz ("My Beloved Beatriz"), 1988's Aventurera ("Adventurer"), and 2002's Mi Gorda Bella ("My Beautiful Fat Girl").
Perhaps Caballero's most important career year was 1989, when he reached international fame starring in Amanda Sabater alongside Maricarmen Regueiro.
This soap opera reached high ratings in many countries, including Mexico, Puerto Rico and (among Hispanics) in the United States.