Now before I begin, I don't claim to know everything about screenwriting. I myself, am only learning, but I thought it would be good to give a list of the screenplays that I have found helped me learn the most. Also I think reading other screenplays is one of the most overlooked practices when people start writing their own for the first time (which completely baffles me, but hey to each their own!).
These are from a variety of genres but I find it extremely beneficial to read screenplays from multiple genres, as each one has its own tips to offer.
That said, if you are planning on writing a romantic comedy, you should probably read WAY more screenplays in that genre. However learning the techniques from films "outside your comfort zone" can help in many ways. So throw in a thriller or horror in the midst of all your romantic comedies, you might be surprised at what you'll learn!
I have tried to include examples that I feel each provide their own individual lesson.
So in no particular order….
1. Casablanca
Screenplay by: Julius Epstein, Philip Epstein & Howard Koch
IMDB: Set in unoccupied Africa during the early days of World War II: An American expatriate meets a former lover, with unforeseen complications
Apart from the fact that it is a timeless classic, Casablanca's real lesson is how to create rich characters. Each character has it own detailed storyline that blends seamlessly with everyone else's. The pacing is brilliant. each scene is pivotal and adds to the overall storyline. (Frankly after reading the script, I feel like the film didn't really do it justice).
2. Lost in Translation
Screenplay by: Sofia Coppola
IMDB: A faded movie star and a neglected young woman form an unlikely bond after crossing paths in Tokyo.
Now whether or not you like this film is irrelevant in terms of what you can learn from the script. It is the epitome of the point that 'The script is not just the dialogue'. It is also a lesson in how to be concise. Yes there are films that require an incredible amount of dialogue and as such the screenplays will be quite long, but this proves that it's not always necessary. There is an art in subtlety.
3. Pulp Fiction
Screenplay by: Quentin Tarantino & Roger Avary
IMDB: The lives of two mob hit men, a boxer, a gangster's wife, and a pair of diner bandits intertwine in four tales of violence and redemption.
As this is the brain child of Tarantino, its going to be like no other type of screenplay you've read. Love him or hate him, his screenplays are a lesson in how to break every rule you've ever been taught. For beginners, I wouldn't say emulating him or throwing out the rule book is necessarily a good thing, but expanding the realms of what is possible is always worth looking into.
4. Rear Window
Screenplay by: John Michael Hayes
IMDB: A wheelchair bound photographer spies on his neighbours from his apartment window and becomes convinced one of them has committed murder.
Apart from the fact that it is a riveting thriller, with rich characters, in my opinion Rear Window is a masterclass in how to create a amazing screenplay based in one location. Enough said.
5. The Social Network
Screenplay by: Aaron Sorkin
IMDB: Harvard student Mark Zuckerberg creates the social networking site that would become known as Facebook, but is later sued by two brothers who claimed he stole their idea, and the cofounder who was later squeezed out of the business.
In contrast to Lost in Translation, The Social Network is all about dialogue. Now I am a little bit biased, because I love Aaron Sorkin and think he is a genius when it comes to dialogue. If you want to learn how to create rapid fire, intelligent articulate and funny dialogue then this is the one for you, (Or anything by Aaron Sorkin for that matter).
Notable Mentions: Back to the Future (How to combine genres and make it realistic), Network & Apocalypse Now
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