Oscars: What Should Have Won Best Picture 1960-1969

Welcome to part 4 of this exercise. As a reminder, we’re going through every year at the Oscars and looking at which film should’ve won Best Picture. I’m only sticking to the films that were nominated. I haven’t seen enough films from every year to choose from all available films, at least not yet.

Today we’re looking at the Academy Awards of the 1960s.

 1960 – The Thirty-Third Academy Awards

What Won Best Picture: The Apartment

What Should Have Won Best Picture: The Apartment

Another undeniable film. Even if I wanted to be different and pick my personal favorite Elmer Gantry, I couldn’t. I’d be wrong anyways. The Apartment was and still is ahead of its time. Even after multiple rewatches it still holds up.

Elmer Gantry from this year is excellent and a film that should have a reclamation. Especially in a post-Trump presidency. It boasts a Best Actor-winning performance from personal favorite Burt Lancaster. Also, I like The Sundowners but I love Robert Mitchum and Deborah Kerr. I understand why people find it boring.

 1961 – The Thirty-Fourth Academy Awards

What Won Best Picture: West Side Story

What Should Have Won Best Picture: The Hustler

People will come for me for this, but Stephen Spielberg’s West Side Story was better. This is a good film, but the whitewashing of some of the Puerto Rican characters has not aged well. Wood and Beymer are verging on bad in this version as Maria and Tony.

The Hustler is a sad, complex, tough film about a man who finds company in a woman but struggle and fail to get out of their own way. It’s a tremendous character study that Paul Newman deserved to win Best Actor.

This could be a great lineup if it weren’t for Fanny sitting there. Terrible film, Leslie Caron deserved better in her career.

 1962 – The Thirty-Fifth Academy Awards

What Won Best Picture: Lawrence of Arabia

What Should Have Won Best Picture: Lawrence of Arabia

Those who know me know this is one of my all-time favorite films. I also believe it is the greatest film I have ever seen. Technically impressive. An astounding breakthrough performance by Peter O’Toole. This film is perfect. There’s no more explanation needed.

Of course, To Kill a Mocking Bird from this year is great. The Music Man is also fun.

 1963 – The Thirty-Sixth Academy Awards

What Won Best Picture: Tom Jones

What Should Have Won Best Picture: Lilies of the Field

The weakest group of five films from the 1960’s and one of the weakest lineups in Oscars history. Tom Jones is not a movie I connected with and I don’t understand how it did with the Academy. Maybe it felt fresh at the time. However, it gave me a headache.

Lilies of the Field falls into the category of Nun movies with little conflict. It’s easily the best version of these films thanks to the charismatic performance by Sidney Poitier. I could watch him hang out with Nuns for hours.

 1964 – The Thirty-Seventh Academy Awards

What Won Best Picture: My Fair Lady

What Should Have Won Best Picture: Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb

My Fair Lady is bloated. Audrey Hepburn is bad and miscast. Gigi is a version of this film that already won Best Picture. Mary Poppins was right there If you wanted to go for a musical. However, that is not my choice because The Sound of Music will win next year.

Dr. Strangelove stands up as one of the best political satires ever made. Still poignant, unfortunately, is why it still feels as fresh as it did in 1964. Plus, Peter Sellers gives three genius comedic performances.

Mary Poppins is a stone-cold classic. Becket is also a worthy recommendation featuring two Oscar bridesmaids, Richard Burton and Peter O’Toole.

 1965 – The Thirty-Eighth Academy Awards

What Won Best Picture: The Sound of Music

What Should Have Won Best Picture: The Sound of Music

Another obvious pick here. Nothing in this lineup even comes close to this film. I love Julie Christie, but I couldn’t even pick one of her two films over The Sound of Music. I also agree with the Academy that Julie deserved Best Actress over Julie Andrews winning back-to-back.

Darling is what Andrew Dominik’s Blonde should have been. Doctor Zhivago is a step back for David Lean but it is still worth at least one watch in your lifetime.

 1966 – The Thirty-Ninth Academy Awards

What Won Best Picture: A Man for All Seasons

What Should Have Won Best Picture: Who’s Afraid of Virginia Woolf?

A Man for All Seasons may be an underrated Best Picture winner. At least in the fact that no one ever talks about it. Built on a great script and two great male lead performances. A Man for All Seasons is good, but Who’s Afraid of Virginia Woolf? Is a masterpiece.

There have only been three films in Oscar history to win the big five (Picture, Director, Actor, Actress, and Screenplay). This should have been another one of those films. Burton never had an Oscar and losing for this should be a crime. Elizabeth’s win here is the greatest Best Actress win ever. To think that it was Mike Nichols' first film is mind-boggling.

 1967 – The Fortieth Academy Awards

What Won Best Picture: In the Heat of the Night

What Should Have Won Best Picture: Bonnie and Clyde

1967 is one of the biggest years in Hollywood. The power had been shifting in the industry, and this year it took shape with films like The Graduate, Cool Hand Luke, and Bonnie and Clyde. In the Heat of the Night is a fine film, but it is not a signifier of where the industry was headed.

Mike Nichols’ film won everything the previous year, at least in my mind. So, I am going with Bonnie and Clyde. This is one of the most important films in Hollywood history. The poster child for The New Hollywood era. The film still holds up today.

All these films in this lineup should be watched at least once in your life, except for Doctor Dolittle. An absolute blunder among these five and the fact that the Academy nominated it over Cool Hand Luke is embarrassing.

 1968 – The Forty-First Academy Awards

What Won Best Picture: Oliver!

What Should Have Won Best Picture: The Lion in Winter

Maybe the shift was a little too fast for the Academy. The only “New Hollywood” film nominated here is Rachel Rachel, which is fantastic. The other four films have tinges of “Old Hollywood”.

Oliver! Is an old-school winner. It’s good and some of the numbers are fun. But, The Lion in Winter is a prickly family affair. Succession set in 1183. It remains an Oscar travesty that Peter O’Toole did not win Best Actor this year.

 1969 – The Forty-Second Academy Awards

What Won Best Picture: Midnight Cowboy

What Should Have Won Best Picture: Midnight Cowboy

Finally, in 1969 the Academy gave the top prize to a “New Hollywood” film. John Sclesginer’s in-your-face film about loneliness and homosexuality may not be as transgressive as it was in 1969. But it remains great.

It earned an X rating for its minimal depiction of homosexuality and remains the only X or NC-17-rated film to win Best Picture. As a signifier of where the industry was headed as well as a landmark gay film, it deserved the top prize.

Butch Cassidy and the Sundance Kid is a classic Z is another prescient political thriller that should be watched.