Best known for his characterizations of two Philip Roth characters, in "Goodbye Columbus" (1969) and "Portnoy's Complaint" (1972), Benjamin had walk-on juvenile parts in some 1950s films and first earned adult recognition on Broadway, starring in Neil Simon's "Star-Spangled Girl" (1966). He had directed "Barefoot in the Park" in London the previous year. Other off-beat acting highlights include "Catch-22" (1970) and "The Sunshine Boys" (1975).
Benjamin made a promising directorial debut with "My Favorite Year" (1982), a comic look at the early days of TV featuring a glorious performance by Peter O'Toole. However his subsequent directorial efforts have not been comparable commercially or critically. A conventional storyteller, Benjamin has worked with a wide assortment of actors in several genres. His second film, "Racing With the Moon" (1984), was a war romance starring Sean Penn and Elizabeth McGovern. Benjamin followed up with a pair of undistinguished comedies: "City Heat" (1984), a period detective comedy starring Burt Reynolds and a surprisingly funny Clint Eastwood and "The Money Pit" (1986), featuring Tom Hanks, Shelly Long, and a collapsing house in a Steven Spielberg-produced comedy which confused laughs with special effects. Benjamin's spy drama, "Little Nikita" (1988), offered the intriguing pairing of Sidney Poitier and River Phoenix, but audiences steered clear. Benjamin also tried his hand at high-concept comedy with "My Stepmother Is an Alien" (1988) with Dan Aykroyd and Kim Basinger and moved on to an action comedy, "Downtown" (1990), with Anthony Edwards and Forest Whitaker. Benjamin regained some degree of critical success that same year with "Mermaids", a touching mother-daughter comedy starring Cher, Winona Ryder, and Bob Hoskins. After a hiatus, he directed Whoopi Goldberg and Ted Danson in the romantic comedy, "Made in America" (1993) and helmed the pallid "Mrs. Winterbourne" (1996), which starred Ricki Lake and Shirley MacLaine.