To me he will always be Neil Klugman, the character he played in the 1969 film Goodbye, Columbus, based on the Philip Roth novella of the same name. The film centered on the relationship between Neil and his girlfriend Brenda Patimkin, played by Ali MacGraw. It touched on class issues between Brenda, a “Jewish American princess,” and Neil, who came from a working-class Jewish background.
Goodbye, Columbus (1969): Neil (Richard Benjamin) and Brenda (Ali MacGraw) argue after Brenda’s mother finds Brenda’s diaphragm.
Benjamin also starred in a sitcom, He & She, with his wife, Paula Prentiss. The two played Dick and Paula Hollister, an urban couple living in New York City. He was a cartoonist and she was a social worker—one of the first working women on TV. The show lasted only one season, but many believe that its style laid the groundwork for shows like The Mary Tyler Moore Show.
“The Phantom of 84th Street,” He & She (Sept. 27, 1967)