I watched all 96 movies that won Best Picture...
And this is what I learned about great storytelling.
TL;DR Version:
I spent 12,700 minutes over 26 years to finish a single goal: ⤵️
Watch every movie that's won Best Picture.
And here's what I learned about great storytelling:
#1. Heart matters more than being flawless.
#2. Put characters (People) before plot (Process).
#3. How you end matters more than how you start.
Regular Version:
I spent 12,700 minutes over 26 years to finish a single goal: ⤵️
Watch every movie that's won Best Picture.
The goal started way back in 1998 when on a random day off from school, bored at home, I decided to pop in a movie called Chariots of Fire sitting in our VHS cupboard.
My life was changed.
It became my favorite movie of all time. Still is.
Now, I’d had a love of movies all my life, and I had been somewhat familiar with the Oscars because we usually watched them each year, especially if Billy Crystal was hosting.
But now I dug in more to what the Oscars were, what it meant for a movie to be named “Best Picture.”
And so I decided to set out to watch every single movie on the list.
I knocked out a ton during high school.
But with a pretty strict “no R-rated movies” rule in our house, there were certain movies that had to wait until I was out of the house:
Movies like American Beauty. And definitely Midnight Cowboy.
But then I got through college and the Best Picture quest took a backseat to life. I was working a full-time stressful job as a social worker, falling in love, buying a business, writing, and becoming a parent.
Then a couple years ago, I remembered, “Oh yeah, I never did finish my Best Picture quest…”
I was only missing a few at that point, and as of last week, I knocked out the final missing piece of the puzzle, the elusive 1933 film Cavalcade. (Which I mostly enjoyed. Kind of like the 1930s version of Downton Abbey.)
Every year in March, I get the same gift from my wife: an entire week to go watch all the Best Picture nominees for the year, so staying current on the quest isn’t a big deal.
But onto the main event.
What did I learn about great storytelling from the Best Pictures?
#1. Heart matters more than being flawless.
Plenty of the Best Picture winners are far from perfect. Gladiator, for instance, has not aged well in my book. But the movie has heart and that’s why it wins over an objectively more flawless film like Traffic.
You could say the same for a movie like The King’s Speech that won over The Social Network. Social Network is arguably the better made film. But King’s Speech makes you feel something. It wins.
#2. Put characters (People) before plot (Process).
The characters make a huge difference in whether the movie sticks with you after the final credits, regardless of the actual plot. And that’s why a movie like Annie Hall beats out Star Wars.
Now, I love Star Wars. It’s an all-time favorite. But the characters are all archetypes. Annie Hall’s characters feel real. Star Wars may have the bigger, better story, but Annie Hall has better characters (and writing).
#3. How you end matters more than how you start.
One of the all-time Oscar debates is “How did Shakespeare in Love win over Saving Private Ryan?” First, you have to consider that this is an American perspective. Most international audiences have no problem recognizing Shakespeare as the better film.
But most of the love for Private Ryan is in the first 30 minutes, the epic and heartbreaking D-Day invasion scene. Shakespeare, on the other hand, has what I consider one of the most beautiful endings ever put on film.
So how do these lessons apply to your and your content?
When you're sharing your own Story in whatever medium:
1. Embrace your flaws and be authentic. (Heart)
2. Put your audience first. (Characters over Plot)
3. Focus on ending well, no matter how you started. (Great endings)
If you want to make sure your book has some Best Picture magic, then book a free 20-minute Q&A and let’s chat.
(Paid subscribers, scroll below for my picks of the Best Written Best Pictures of each decade of the Oscars.)
Until next time, keep telling your story.
Did this help you? If so, share this with someone you know via the handy little button below.
Automate your savings (and help support this newsletter) by signing up for the Acorns app. Oh yeah, and get a $5 thank you gift from them when you do.