I got a Twitter question from @JulianRamos_
Any books or novels you would recommend a high school senior / aspiring screenwriter to read?
Boy, did you come to the right place. Thanks to membership at several very well-stocked libraries, I pretty much read every screenwriting book published by the time I was in my early-to-mid twenties. After reading dozens of those books, I came away with the feeling that many of the books were saying exactly the same thing. That theory was somewhat proven by my friend J.J. Patrow in this blog post. He compares the storytelling philosophies of Aristotle, Joseph Campbell, Syd Field, Blake Snyder, Peter Dunne, Drew Yanno and then visually demonstrates the similarities via chart. So know that while there are probably hundreds of screenwriting books out there, a lot of them are going to tread on the same ground.
First, formatting is something you want to have drilled into you early on so you don't screw it up. For that reason, I'd make The Screenwriter's Bible: A Complete Guide to Writing, Formatting, and Selling Your Script by David Trottier one of your first reads.
From there, I'd say that it helps to get a sense of three-act structure and what that means in terms of breaking and developing your story. There are at least a hundred books that'll cover this in some form - I recommend Blake Snyder's Save the Cat. He's taken some flack for the way he somewhat rigidly adheres to a formula, but I think it helps to give beginners some structure. His 15-point beat sheet is a good way to get the hang of writing a film. It also can be of use in helping you dissect films that you like, making it a stepping stone to getting inside the story and understanding why some screenplays work and some don't.
After that, I'd suggest immersing yourself in some more personal memoirs from working writers. It's always good to balance the nuts and bolts education with straight talk about what it's really like not just to develop screenplays, but also work in the industry. There's more to being a screenwriter than just writing scripts, if you know what I mean. To that end, these are among what I'd consider required reading:
Adventures in the Screen Trade by William Goldman
Which Lie Did I Tell?: More Adventures in the Screen Trade by William Goldman
Billion-Dollar Kiss: The Kiss That Saved Dawson's Creek by Jeffrey Stepakoff
Tales from the Script: 50 Hollywood Screenwriters Share Their Stories
Go to your local library and find where those books are. I can almost guarantee that you'll probably find a dozen other worthwhile books in a similar vein right next to those on the shelves.
Also, for extra credit, read Homicide: A Year on the Killing Streets by David Simon. It's not a screenwriting book. You'll find it in True Crime. Then, go watch the first season of Homicide: Life on the Street, the NBC series inspired by the book. There are a great many storylines and characters that are adapted quite closely from the book, but you'll also notice at least as many differences in character and plot. Some characters are merged, others are invented out of whole cloth. Make yourself aware of what changes have been made and ask yourself why those changes were necessary.
Hopefully, that'll give you some insight into how even the most interesting real-life stories often need to be restructured and re-conceived when adapted as drama. A lot of first-time writers try to adapt things from their lives without understanding that real life is boring and often without the construction that makes drama interesting.
That and Homicide's just an awesome show. David Simon wrote the book when he was a journalist for The Baltimore Sun, but when it became a series, he wrote a few episodes and this started his career as a TV writer/producer. He's since gone on to create The Wire and Treme.
That should be enough to get you started. Be warned that the more screenwriting books you find, the more tempting it is to say, "Well, I'll write my script after I read one or two more of these, just so I'm REALLY prepared." Don't allow reading these books to become an exercise in procrastination.
Does anyone else have what they'd consider essential reading?