Two Shot: The Worst Best Picture Oscar Winners? What They Were And What Should Have Won Instead

Editor’s note: Deadline presents the 13th episode of Two Shot, a video series in which Pete Hammond and Todd McCarthy tackle the artistry of films. Each has reviewed and written about the craft for decades and built a remarkable breadth of knowledge of films past and present. What we hoped for when we asked them to do this was a concise, mature and thoughtful conversation comparable to what we saw from Roger Ebert and Gene Siskel.

In today’s Two Shot, we do what everybody does this time of year: argue back and forth about the Oscars. But this week we are not arguing about what we think should or will win on March 27 at the Dolby, but rather what already did win in the previous 93 years the Academy has been around, and how often, in our humble opinion they have gotten it wrong. Admittedly this comes from the rear-view mirror in examining what Best Picture winners have, and have not, stood the test of time beginning with the earliest Best Picture champs, including one that we deem not only shouldn’t have won but is actually unwatchable now.

We decided to pick five years apiece where we argue against the Academy’s choice and give our reasons as to why another specific film that year should have won instead. And indeed there are even years when the film we individually pick wasn’t even a Best Picture nominee — which makes the omission, yes in retrospect, even more egregious.

This is a fun one as we choose the alternate Best Picture winners, and join us next Tuesday as well when we will hash out this year’s race.

Check out this week’s conversation in the video above.

—

Hammond has been Deadline’s Awards Columnist for the past decade, covering what now seemingly is the year-round Oscar and Emmy seasons. He is also Deadline’s Chief Film Critic, having previously reviewed films for MovieLine, Boxoffice magazine, Backstage, Hollywood.com and Maxim, as well as Leonard Maltin’s Movie Guide, for which he was a contributing editor. In addition to writing, Hammond also hosts KCET Cinema Series and the station’s weekly series Must See Movies.

McCarthy is a veteran trade publication film critic, columnist and reporter who has also written several acclaimed books and documentary films. He served two stints on the staffs of Variety and The Hollywood Reporter and extensively covered film festivals internationally for both publications. His film Visions of Light: The Art of Cinematography won the best documentary prizes from the New York Film Critics and National Society of Film Critics associations, and he won an Emmy for writing the documentary Preston Sturges: The Rise and Fall of an American Dreamer. He also directed the documentaries Man of Cinema: Pierre Rissient and Forever Hollywood.