My Quest to See Every Best Picture Movie

Jason Heltzer
7 min readMay 28, 2020

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“How do you not know that movie?” my wife would routinely ask. Surely there are worse ways to emasculate a man. You see, my wife was the chief executive officer of the movie review site emoviecritic.com. While it did not become a dot com titan, it was an effective way for her to write off movie tickets as a business expense. It’s what you expect of a tax accountant. A natural consequence is that she’s seen a lot of movies.

Her regular astonishment at my movie illiteracy became increasingly hard to endure.

At a weak moment, I decided to shove all-in and watch every single movie that won the Academy Award for Best Picture. I was then confronted with a decidedly first-world problem: how to find the time with a newborn and a busy job. There just wasn’t any time, not even to go to Home Depot or Bed, Bath, & Beyond on weekends.

Implementation

I miss Steve.

Salvation arrived on October 12, 2005: the 5th generation of the Apple iPod began supporting video playback. I am an efficiency freak, and if I could watch movies while I was commuting on the El, it would be “found time.” I just had to accept that I’d be watching movies in 20–30 minute increments, twice a day. To further reduce the problem, I decided not to re-watch movies I had already seen, leaving roughly 50 movies and perhaps 100–150 hours.

I set up a system of getting a Netflix DVD in the mail, ripping it using software called Handbrake, and syncing via iTunes the resulting files to the iPod (keep in mind Netflix didn’t introduce streaming for another two years, and even when it did it, was restricted to wifi and then when available over cellular, it was prohibitively expensive given data plans and my budget). Different times!

This approach wasn’t fool proof, and some movies were hard to find. The first winner from 1927, Wings, was not available commercially. I watched it in 14 increments on Youtube. Being a silent movie, this is the only one that I’ll admit I watched while using the loo at work. By the way, it’s a superb movie!

The Journey

The Great Ziegfeld wasn’t so great.

Trampling through 80 years of an artform in such an efficient manner and short period of time was luxurious. It was, however, occasionally punctuated by dull moments. There are several adaptations of grand Broadway performances which I trudged through (The Broadway Melody (1929), The Great Ziegfeld (1936), The Greatest Show on Earth (1952)). There were times where the project stalled, and I found myself consuming the 20 minute bite sizes among multiple movies as if they were tapas. Linearity is overrated.

What order did I undertake? Random. It wasn’t a deliberate decision, but retrospectively, it was essential to maintain interest. I have wondered if watching in chronological order would have given me a perspective on how movie making has evolved, but I submit that juxtaposing two great movies made 60 or 70 years apart can make those improvements rather stark, versus watching the glacier carve.

It took me about five years to get through all 50 movies.

Instant Aging

Hard to believe, but yes, at one time, Marlon Brando was young.

Smart phones weren’t prevalent when I started the process. It wasn’t until I had an iPhone that it became a routine to check the IMDB entry for each movie after watching it. There surprises awaited! After watching On the Waterfront (1954), I remarked to my wife that the lead actor was just incredible. I was shocked when I learned it was Marlon Brando. How did I not figure that out? Well to me, Marlon is the Don in Godfather (1972). Although he was 48 when he filmed it, he was outfitted to be much older in the film. In On the Waterfront he was 30 years old, so I didn’t recognize him. Similarly, seeing Alec Guinness in Lawrence of Arabia (1962) fifteen years before he would become Obi Wan Ben Kenobi was a treat. For some of the older movies, I got into the habit of looking at current pictures of the actors I didn’t know, “instantly” aging them 10, 20, 30 years. Again, yet another advantage of ignorance! This also applied as famous quotes snuck up behind me, like, “I could have been a contender” and “Play it, Sam” (often misquoted as “play it again, Sam”).

Here Sam is playing it again.

Films robbed

Andy looks like he’s playing a defensive game of checkers while Red is attacking. That’s the opposite of their spirits. This might be the only flaw in the movie.

Given that politics and history conspire in decisions by the Academy, it is no surprise that some incredible movies were snubbed. Exhibit A and B in my testimony are Shawshank Redemption (1994) and 12 Angry Men (1957). Shawshank lost to Forrest Gump (1994), which no doubt is fine cinema and has burrowed a place in every day expressions and even inspired an unnecessary restaurant chain. But it is no comparison against the force of Shawshank. I originally watched it by accident because the intended movie was sold out, a twist of fate for a movie that I hold out as my favorite. I continue to assert to this day that every line seems expertly crafted, the acting genuine, and the story of traversing despair to hope an eternal one. I still get emotional when watching it and I have seen it 30 or 40 times. In my single days, aside from smoking a cigarette, there was no faster way for me to lose romantic interest in someone than not loving that movie. It was a litmus test.

I served on a jury once for an attempted murder trial and it was a formative experience. Don’t try to avoid jury duty.

While less of a travesty, 12 Angry Men (1957), is an acting masterpiece. In contrast to the vistas of Lawrence of Arabia (1962) and Out of Africa (1985), and the visual whimsy of Avatar (2009), a vast majority of 12 Angry Men is one, dull set. In fact, all but three minutes of the film are in the nondescript jury room. That leaves the film naked to depend on the power of the story and acting, which it does gracefully. The film that won that year, A Bridge On The River Kwai (1957) is a great film, but does not inspire me as does 12 Angry Men.

Star Wars (1977) was a victim of timing, since it was up against Rocky (1977). The next year, Annie Hall (1978) won. Given the Academy does not select comedies frequently, I have always felt Star Wars would have beaten Annie Hall as easily as Han Solo could beat you in a Kessel run. The year before was One Flew Over The Cuckoo’s Nest (1976) which would have been tough.

Here Han is making an appeal to the Academy.

Maltese Falcon (1941) is noticeably absent the Best Picture list, having lost to Hitchcock’s Rebecca (1941). Masses believe that Maltese is the best film ever made, and while I am not a Maltese acolyte, I thought it was way more engrossing than Rebecca. Sorry, Alfred.

The Best Movie Ever

When people learn that I’ve seen every best picture movie, dependably they ask, “what’s the best one?” That’s just an impossible question to answer. How do you compare Lord of the Rings: The Return of the King (2003) with One Flew Over the Cuckoo’s Nest (1975) and The Sound of Music (1965)? You cannot pick one.

And who am I to judge? I’ve never taken a class on movies. Other than The Adventures of Peter Puck (1991), which I helped make during high school in about two hours to cure boredom, I’ve never been involved in making a movie. Since you are wondering, Peter was a rough-and-tumble stuffed puck won at a Dave and Busters, who met a cruel end in an unfortunate encounter with fire crackers/on-set pyrotechnics.

Here are some movies that did stand out to me, organized by category:

  • War: All Quiet on the Western Front (1930), The Deer Hunter (1978)
  • Epics: Casablanca (1943), Gone with the Wind (1939), Lawrence of Arabia (1962)
  • Mobs: On The Waterfront (1954), Godfather (1972), Godfather II (1974)
  • Police: In the Heat of the Night (1967), The Sting (1973)
  • Biopics: The Last Emperor (1987), Ben-Hur (1959)
  • Discrimination: In the Heat of the Night (1967), Green Book (2018), Schindler’s List (1993), The Life of Emile Zola (1937)
  • Mental disability/illness: One Flew Over the Cuckoo’s Nest (1975), A Beautiful Mind (2001), Silence of the Lambs (1991)
  • Inspiration: Rocky (1976), Kramer vs. Kramer (1979)

Turning Appreciation to 11

This is Spinal Tap still holds up.

It is easy to conclude, as I did early on, that some of the older movies don’t match up to contemporary flicks. “The craft evolved!” you tell yourself. What I absorbed is that it is impossible to fairly judge or properly enjoy a movie without the historical context. If there is one thing I really gained from this process, is learning how to use historical context to more deeply enjoy both contemporary and older movies.

That’s the subject of my next post.

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Jason Heltzer

Dad, venture capitalist at @OriginVentures, @chicagobooth professor, Chicagoan. I was a nerd before it was cool to be a nerd.