Based on one of author Phillip Roth's shorter works, Goodbye Columbus stars Richard Benjamin as Neil, a young man of humble means who falls in love with Jewish-American-princess Brenda (Ali MacGraw). Their romance is out of the question so far as Brenda's suburbanite parents are concerned, so Neil and Brenda rendezvous in some of the sleaziest motels ever seen in a 1960s film (and that assessment includes The Bates Motel). Unwilling to take birth control pills because they upset her tummy, Brenda opts for a diaphragm, which unfortunately is discovered by her mother. Their rocky relationship comprises the bulk of the film. The trendy, New Wave-influenced direction by Larry Peerce gained a great deal of critical attention in 1969, notably such self-indulgent devices as having a close-up of a girl's navel dissolve into a long-shot of a swimming pool. Far more memorable is Peerce's amusingly straight-on depictions of upper-class Jewish/American social functions. In their film debuts, Richard Benjamin and Ali MacGraw are appealingly awkward; the more memorable performance is delivered by Michael Meyers as MacGraw's adenoidal younger brother.
~ Hal Erickson, All Movie Guide