Goodbye Columbus (1969)

A middle class Jew (Richard Benjamin) from the Bronx enters a summer romance with the spoiled daughter (Ali MacGraw), a Radcliffe student, of an affluent Jewish family who've risen in the world. Based on the award winning novella by Philip Roth and directed by Larry Peerce, this is a sharp eyed look at class differences, cultural assimilation and the generation gap. Though the film appears to be contemporary (circa 1969 contemporary), the film feels like the 1950s, the era Roth's novel was written. Though the inside look into middle class Jewish life is fascinating to a goyim, if the film weren't written and directed by Jews, some of the more stereotypical portrayals border on anti-Semitic, particularly a rather mean spirited wedding sequence. But for its portrayal of the emerging of the 60s generation, it holds up much better than THE GRADUATE. The two leads are terrific, Benjamin perfectly inhabits the conflicted Neil, unable to relate to either the social climbing middle class nouveau riche or the emerging alternate lifestyles. MacGraw is near spectacular here, a case of the right actress in the right part, she embodies the Jewish American Princess so effortlessly that one can almost forgive the mediocrity of the career that followed. The tuneful score is by Charles Fox with songs by the pop group, The Association. With Jack Klugman and Nan Martin.