This was such a momentous Oscar race that there’s a whole book — Mark Harris’ excellent Pictures at a Revolution — about it. Harris details how this race was emblematic of the massive changing of the guard then underway throughout American filmmaking. The old-school studio film was represented by Doctor Dolittle, 20th Century Fox’s costly musical flop, which muscled into the race on the strength of Fox’s marketing machine. In the Heat of the Night and Guess Who’s Coming to Dinner were also both conventional studio films, but ones that addressed hot-button issues of race at the height of Civil Rights-era turmoil. The Graduate (pictured) also addressed contemporary issues (the generation gap, the sexual revolution), but in a hip, comical way, and with a folk-rock soundtrack. Bonnie and Clyde was a period drama but the most forward-looking film of them all, borrowing its style from the French New Wave and pushing the envelope with its depiction of sex and violence.
In the end, the Academy split the wealth; Bonnie won Supporting Actress (for Estelle Parsons) and Cinematography; Dinner won Best Actress (for Katharine Hepburn) and Original Screenplay; Graduate won Best Director (for Mike Nichols); Dolittle won Best Visual Effects and Best Song (“Talk to the Animals”), and Heat of the Night took Best Actor (Rod Steiger), Adapted Screenplay, Sound, Editing, and Best Picture. It wasn’t as radical a statement as giving everything to Bonnie and The Graduate would have been, but it was still a sign that old Hollywood was giving way to a new guard.