You can’t often look back at an Academy Awards and pinpoint a change in the industry. Sure, there are always breakout performances, budding young directors, and new innovations highlighted each and every year, but to see the changing identity of Hollywood encapsulated among the nominees is pretty extraordinary. It is no secret that the 40th Academy Awards, held on April 10, 1968, was an important year for the ceremony: esteemed film critic Mark Harris wrote an entire book about this night, Pictures at a Revolution. This re-evaluation of the nominees through the scope of Bonnie and Clyde will obviously pale in comparison. But I hope it will be fun.

Of the night’s nominees, Bonnie and Clyde and Guess Who’s Coming to Dinner led the way with 10 nominations each—Bonnie and Clyde received 2 nominations in the Best Supporting Actor category. Given the strong and diverse films that were nominated, the winners were fairly spread out. In the Heat of the Night was the biggest winner, however, with 5 wins, including Best Picture and Best Actor. Costume musical Camelot won three statues, though none in the major categories, while three films won 2 apiece.

Before I get started, my typical disclaimer: I only consider the nominated films for each category, even if I might prefer something that was left out of the discussion. Typically, that eliminates many great films that weren’t recognized at the time, though 1967 highlighted most of the mainstays. A few films that were missing: Playtime, Belle de Jour, Le Samouraï, and Point Blank.

Best Supporting Actor

The Nominees:
John Cassavetes, The Dirty Dozen
Gene Hackman, Bonnie and Clyde
Cecil Kellaway, Guess Who’s Coming to Dinner
George Kennedy, Cool Hand Luke
Michael J. Pollard, Bonnie and Clyde

Who won: George Kennedy, Cool Hand Luke
Who should have won: Gene Hackman, Bonnie and Clyde

Two nominations from Bonnie and Clyde may have split the vote among the Academy but these are the best two performances in the category for me. While Michael J. Pollard is much more fun to watch on screen as the young car mechanic swooped up by the Barrow gang, Gene Hackman is undoubtedly the better actor of the two. This is far from Hackman’s best performance [which is something I always like to consider when re-evaluating these awards] and he later won two Oscars, but Buck Barrow is a strange emotional center to Bonnie and Clyde. He is something like an agent of chaos, helping to spur his more famous brother into the criminal life, and the performance matches that energy. He’s just damn cool.

Best Supporting Actress

The Nominees:
Carol Channing, Thoroughly Modern Millie
Mildred Natwick, Barefoot in the Park
Estelle Parsons, Bonnie and Clyde
Beah Richards, Guess Who’s Coming to Dinner
Katharine Ross, The Graduate

Who won: Estelle Parsons, Bonnie and Clyde
Who should have won: Katharine Ross, The Graduate

I love watching Estelle Parsons as shriek and scoff her way through Bonnie and Clyde as Blanche, but the character is just irritating enough that I decided to go another way with it. Mildred Natwick is a similar character as a tough-to-please mother of Jane Fonda’s newlywed and while she’s fun, there isn’t as much range there.

This is a tough call between Carol Channing and Katharine Ross, with Ross getting the nod for the more well-rounded performance and more iconic character. Channing was a revelation to me, though—she has a smaller role but I couldn’t take my eyes off her whenever she was on screen.

For Ross, her final two scenes are all-time moments in cinema and I couldn’t overlook that. Her shriek when Ben breaks up her wedding and the look of disillusionment in the final frames are unforgettable. She might be the third wheel in The Graduate but she holds her own.

Best Cinematography

The Nominees:
Bonnie and Clyde
Doctor Dolittle
The Graduate
In Cold Blood

What won: Bonnie and Clyde
What should have won: In Cold Blood

While Camelot and Doctor Dolittle are big epics that bring you into a huge world with its cinematography, those films aren’t interesting or distinct enough to match up against the smaller but visually impressive Bonnie and Clyde, The Graduate, and In Cold Blood.

Thinking over The Graduate, it doesn’t seem like the kind of film that would be championed for its cinematography. But then you think of its lasting images—Ben floating in the pool, Mrs. Robinson’s leg surrounding her young rendezvous—and it makes sense.

Still, it comes down to Bonnie and Clyde and In Cold Blood for me. When I think about Bonnie and Clyde’s more kinetic camerawork I can’t help but wonder how it wasn’t nominated for Best Editing, which is the more stunning technical achievement in my mind.

It might be cliche to give a cinematography award to the film shot in black-and-white, but In Cold Blood’s camerawork is absolutely stunning and works thematically, too. The dark and cool tones match the dark and cool narrative perfectly. It is a bleak and ominous crime story that is completely made within this image. I can’t imagine the film having nearly as much effect if it had been shot differently.

Best Costume Design

The Nominees:
Bonnie and Clyde
The Happiest Millionaire
The Taming of the Shrew
Thoroughly Modern Millie

What won: Camelot
What should have won: Thoroughly Modern Millie

On paper, Camelot is definitely the obvious choice to win this award, as a fantasy epic with the dresses, the crowns, and the full leather suits. But I found the costuming to be inauthentic, more like 60s clothing than of the historical period. I guess that isn’t really a reason to disqualify it, but it just didn’t sit with me right. [It doesn’t help that Camelot is a pretty awful film…]

Bonnie and Clyde and Thoroughly Modern Millie take place in a similar era, one before and one after the Great Depression kicked in. Both feature fun dresses and well-tailored suits, with Bonnie and Clyde’s a little shabbier to denote the times while Thoroughly Modern Millie is in full-on glamour mode. This glitziness is enough of a tie breaker for me. When Julie Andrews, Mary Tyler Moore, and Carol Channing are all fabulously dressed it is wonderful to watch.

Best Original Screenplay

The Nominees:
Bonnie and Clyde
Divorce American Style
Guess Who’s Coming to Dinner
Two for the Road
The War Is Ove

What won: Guess Who’s Coming to Dinner
What should have won: Bonnie and Clyde

Unfortunately, I was only able to see two of these nominees before writing this post. Also unfortunately, the nominees in the Adapted Screenplay category, particularly In Cold Blood, In the Heat of the Night, and The Graduate, are much stronger screenplays overall.

If Guess Who’s Coming to Dinner deserved any award this would probably be it. It is a big message movie that has a reputation of being more didactic than it actual is. Bonnie and Clyde explores its themes and messages more subtly and overall has much more energy from start to end. So, while the script isn’t the first thing I think about when I consider Bonnie and Clyde, the way it tells its story is more compelling.

Best Actress

The Nominees:
Anne Bancroft, The Graduate
Faye Dunaway, Bonnie and Clyde
Edith Evans, The Whisperers
Audrey Hepburn, Wait Until Dark
Katharine Hepburn, Guess Who’s Coming to Dinner

Who won: Katharine Hepburn, Guess Who’s Coming to Dinner
Who should have won: Faye Dunaway, Bonnie and Clyde

This is an extremely tough field to call.

If you are like me, you’d never heard of Edith Evans or The Whisperers, a small little kitchen sink-esque drama from the U.K. Really, it is a shocking nomination given what I imagine was a tiny profile and an actress with an infinitesimal amount of clout when compared to her competitors. Typically when a small performance is nominated [let’s be honest, though, nowadays that small performance usually comes from an A-lister taking on a small passion project] I have to assume the performance is just so damn good that it couldn’t be ignored. As for Evans, it is a tragically sad showing as an elderly woman losing her grip on the world. The Whisperers could only be found in a decent enough transfer onto YouTube but really isn't required viewing, though Evans is the unquestionably the best part.

I’m not sure how I could even possible rank the remaining four performances, they are all legendary. My gut tells me to go with Dunaway over Hepburn [and it very much is a gut call] because it just feels like a more vibrant performance. It is hard to take your eyes off of Dunaway throughout Bonnie and Clyde as she goes through the gamut of big emotions—joy, anger, grief, sentimentality, everything. Dunaway finally won an Oscar 11 years later for Network but I’ll always associate her as Bonnie Parker.

Best Actor

The Nominees:
Warren Beatty, Bonnie and Clyde
Dustin Hoffman, The Graduate
Paul Newman, Cool Hand Luke
Rod Steiger, In the Heat of the Night
Spencer Tracy, Guess Who’s Coming to Dinner

Who won: Rod Steiger, In the Heat of the Night
Who should have won: Paul Newman, Cool Hand Luke

You thought the Best Actress race was loaded? Look at these nominees. Five iconic performances [OK, maybe more like four iconic performances. Sorry Mr. Tracy, though he is certainly great]. Speaking of Spencer Tracy, this was sadly one of the few notable instances where the nomination was made posthumously, as the legendary actor died just 17 days after the completion of Guess Who’s Coming to Dinner. I can’t fault the recognition.

I’ll break the rules here for a minute and note the most notable absence, Sidney Poitier, for not one but two films: In the Heat of the Night and Guess Who’s Coming to Dinner. Interestingly, as you’ve surely noticed, both of those films were represented by Tracy and eventual winner Rod Steiger. In both cases, you could easily argue that Poitier was the lead actor, probably more so in Guess Who’s Coming to Dinner—one has to wonder how Tracy’s death may have swayed the Academy, however cynical that may sound.

As for Poitier’s other co-star, Rod Steiger is very good in In the Heat of the Night in a very difficult role. Seeing the film for the first time, my expectations of a by-the-numbers Southern racist cop were completely shattered, much because of Steiger’s nuanced performance. The character speaks his mind and has some troubling things to say about his de facto partner, but he takes his position and the investigation seriously. It is a similar type of character and performance as one of my favorite performances ever, Orson Welles as Hank Quinlan.

Steiger’s competition is tough, however, and he doesn’t deliver my favorite performance of the bunch. I could have sided with either the comic bravado of Warren Beatty or the youthful disillusionment of Dustin Hoffman, but this is really a no-brainer for me. This might just be a personal pick, but I’ve always loved Cool Hand Luke [it would have been nominated for Best Picture in my world] and Newman is the absolute center of that. He is just so damn cool. He’s the ultimate rebel. And it’s the most truly iconic performance of the year.

Best Director

The Nominees:
Richard Brooks, In Cold Blood
Norman Jewison, In the Heat of the Night
Stanley Kramer, Guess Who’s Coming to Dinner
Mike Nichols, The Graduate
Arthur Penn, Bonnie and Clyde

Who won: Mike Nichols, The Graduate
Who should have won: Arthur Penn, Bonnie and Clyde

If you rewind back to the very first in the Re-thinking the Academy Awards series, where I thought over the films of 1966, I gave Mike Nichols the nod for his debut directorial effort, Who’s Afraid of Virginia Woolf? Part of my internal reasoning was that was a clearer victory than the following year when the young auteur beat out Arthur Penn’s work in the landmark Bonnie and Clyde. So, I’m going to keep kayfabe and give Penn the award.

Of course, Penn [and sure, Nichols] deserves it. He didn’t single-handedly shepherd the film industry into the New Hollywood but his film is probably the most notable in the transition. His mixing of trending film techniques with a classic genre story that lives in past makes for an incredible experience.

Honestly, though, Richard Brooks was tough to deny. In Cold Blood is probably the most visionary of the films nominated and while a lot of the film’s hard edge come from its source material, Brooks creates a nightmarish, disturbing world.

Best Picture

The nominees:
Bonnie and Clyde
Doctor Dolittle
The Graduate
Guess Who’s Coming to Dinner
In the Heat of the Night

What won: In the Heat of the Night
What should have won: The Graduate

To me, this mostly comes down to Bonnie and Clyde and The Graduate, which are the head of the class. On quick sight, Doctor Dolittle is the one that sticks out, maybe because of the tone and reputation of the Eddie Murphy remake, but like other films I explored for the first time, the original is much different than my expectations. Still, the vet-who-talks-to-animals musical adventure is on a lower tier than its competition.

Guess Who’s Coming to Dinner and In the Heat of the Night share the theme of race relations and both come off today without totally feeling stodgy or purely of the mid-60s era—a legitimate accomplishment. In the Heat of the Night hides its capital-I importance by being an entertaining hard boiled crime story. Subsequently, that takes off a little of the shine. I have no issues giving a well-oiled machine Best Picture, but not when the other competition is so noteworthy.

So, why The Graduate over Bonnie and Clyde? The latter is more visually inventive but also a bit more scattered. Overall, The Graduate is the more complete film and a better encapsulation of the themes and sentiments of the time. This comes down to a re-evaluation of representation, really, and to me looking back at the start of the New Hollywood era, The Graduate simply feels more like the era. When you’re picking between two undeniable masterpieces, especially in a purely historical context, this is enough of an edge.

Overall, however, Bonnie and Clyde did remarkably well in this re-run of the 40th Academy Awards, netting three awards for a total of four. While I didn’t agree with the Academy on a single award, this comes down to personal preference and the incredible mix of films that were honored. Because of that, there were few of these choices that I felt were total steals, few where the Oscars clearly got it wrong. That’s what makes this such a fun Oscars to look back on and why this particular year has been remembered so fondly.