Throughout his film career, Richard Benjamin trafficked in neurotic, high-strung, self-involved upper-middle-class characterizations. While attending the New York High School of Performing Arts, Benjamin made his first professional stage appearances, and reportedly showed up in a handful of movie bit roles. He continued his theatrical training at Northwestern University, where he met actress Paula Prentiss, whom he married in 1961. At first, Hollywood was more interested in Paula than in Dick; thus, while Paula was co-starring with Jim Hutton at MGM, her husband was still performing on stage. In 1965, Benjamin directed the London production of Neil Simon's Barefoot in the Park; the following year, he made his Broadway acting bow in Simon's The Star Spangled Girl, earning a Theatre World Award in the bargain. Co-starring with wife Paula, Benjamin appeared in the 1967 TV situation comedy He and She, which gained a loyal cult following but was considered too New Yawk-ish for the hinterlands. Even so, He and She made Benjamin a name-above-the-title star, and it was in this capacity that he made his film adult screen appearance as angst-driven collegiate Neil Klugman in Goodbye Columbus (1969). He went on to play Major Danby in the all-star Catch-22 (1969), monumentally insensitive husband Jonathan Balser in Diary of a Mad Housewife (1970), the self-abusive (in every sense of the phrase) title character in Portnoy's Complaint (1972), the hero-by-default in Westworld (1973), ulcerated agent Ben Clark in The Sunshine Boys (1976) and erstwhile vampire hunter Dr. Jeff Rosenberg in Love at First Bite (1980). Benjamin participated in another cult-TV item in 1978, when he starred in the 6-episode sci-fi lampoon Quark. In 1982, he made his film directorial bow with My Favorite Year (1982), a rollicking nostalgiafest inspired by TV's Golden Age. Since that time, Benjamin has favored directing over performing.