The first starring role for both Richard Benjamin and Ali MacGraw came about in which 1969 film based on a Philip Roth novel?

The 1969 film "Goodbye, Columbus" served as a significant launchpad for the careers of its two main actors. For Richard Benjamin, it was his first lead role in a film, and for Ali MacGraw, it was her first starring role, a performance that earned her a Golden Globe Award for Most Promising Newcomer. The movie is an adaptation of Philip Roth's 1959 novella of the same name, which won the prestigious National Book Award for Fiction. The story explores the budding romance between a working-class Jewish man, played by Benjamin, and a wealthy, Radcliffe-attending young woman, portrayed by MacGraw.

The film adaptation was both a critical and commercial success, praised for its sharp and humorous portrayal of class differences and Jewish American life in the late 1960s. The screenplay, written by Arnold Schulman, was highly acclaimed and received an Academy Award nomination. The movie's title is a reference to a record owned by the brother of MacGraw's character, which nostalgically recalls his college athletic days at Ohio State University in Columbus.

Following "Goodbye, Columbus," both actors went on to have notable careers. MacGraw became an international star with her next major film, "Love Story." Benjamin continued to act in prominent films throughout the 1970s, including "Catch-22" and "Westworld," and later became a successful director with films like "My Favorite Year." The success of "Goodbye, Columbus" also benefited from the popularity of another Philip Roth novel, "Portnoy's Complaint," which was a bestseller at the time of the film's release.