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Where Genre Has No Limits: Spotlight on Screenwriter David Hal Chester

Script contributor Nanea Taylor speaks one-on-one with screenwriter David Hal Chester about his writing journey, the characters he's drawn to write about, and much more!
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In this series, we talk to screenwriters about their works in progress and what drew them to screenwriting. This time around, we got a chance to sit down with up-and-coming screenwriter David Hal Chester.

David Hal Chester is an American screenwriter and short filmmaker based in Tokyo. He writes female-driven dramas, with a strong focus on dysfunctional family dynamics. A Los Angeles native, David’s skills as a songwriter and pianist initially brought him to Japan. He was soon presented with so many creative opportunities, he decided to set down roots. Realizing he wasn't seeing stories that were important to him, he turned to screenwriting and filmmaking.

To date, he has written seven commissioned features, four streaming on either Netflix, Amazon Prime, or Lifetime TV, with three currently in production. His original feature screenplays Tillie and Big Sister have placed multiple times as screenwriting competition finalists. David has also produced, written and/or directed four shorts, most notably The Lesson, which won the Tokyo LGBT Film Festival “Grand Prix” and the Torino GLBT Film Festival “Best Short Film.”

David’s writing has benefitted from participation in Corey Mandell’s screenwriting workshops, Roadmap Writers’ Top Tier group, and mentoring by writer/producer Ellen Sandler (writer and co-executive producer on the hit TV series Everybody Loves Raymond). When David isn’t obsessing over the seven volumes of Mad Men scripts, you can find him hunched over his desk writing a screenplay or teleplay (or, more likely, rewriting them).

What is your favorite genre to write? What genre are you looking forward to writing?

I seem to gravitate toward dysfunctional-family, female-driven drama. One day, though, I would love to get back to comedy, since that’s where I started.

Tell us about a WIP that is in your favorite genre.

I am working on a biracial LGBTQ drama set in the cloistered world of a music college in the 1970s.

If you could give any tips to an upcoming writer on how you handle multiple story ideas, what would you tell them?

Ideas strike when they want to, not when it’s convenient for us. Create folders on your computer and give your projects working names. When inspiration strikes, throw your ideas in the appropriate folders. One day, you’ll be ready to sit down and write the script, and you will have captured your “lightning moments” and be able to use them.

David Hal Chester

David Hal Chester

Tell us about the moment you realized that you wanted to be a writer.

I had spent the majority of my life as a musician/songwriter. But I always had some inkling I wanted to write screenplays, I just thought it was beyond me. Then, on my 45th birthday, I looked in the mirror. It was like someone slapped me and said, “You are supposed to be writing screenplays!” That was it! I changed course and never looked back. I guess I had to wait for my mind to catch up with my heart.

What story, film, or novel has left an indelible impact on you as a writer?

The film Erin Brokovich. I love how this woman, who was really sinking in her personal life, ended up being the catalyst for a lawsuit that brought an evil energy corporation to its knees.

The novel Tillie, a long-forgotten American novel, which my co-writer and I based our screenplay on. A young farm girl with a thirst for learning battles her tyrannical father to get an education. The character was incredibly inspiring.

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What usually inspires your creativity?

Injustice against others. I feel compelled to tell stories about people rising up against oppression to achieve their dreams.

How do you decide which idea to start on first?

Ideas have to grab me by the throat. I have tons of ideas that float through my head, but only a few rise to the surface. So, the ones that “bother” me the most definitely get my attention first.

How do you handle writer's block?

I must say that I have never had writer’s block. But, if I get stuck, here are my tricks: I go for a walk and clear my mind. Solutions will come to me. Also, this sounds dumb, but, I wash the dishes. Whenever I do some activity with water, my mind clears up and I know exactly what I have to write.

If you could work as a showrunner for your favorite show, how would you choose the best writers to fill the writer's room?

I would reach out to the wonderful writers I’ve connected with via social media and whose work I’ve read. I’ve seen their love, dedication, and commitment. Most have no representation, some might be considered “too old,” others are “outsiders.” All of them are tenacious. Those are the first writers I hire.

What story idea have you started to work on next?

I survived a harrowing experience during the L.A. riots in the ‘90s. I have a story of a small group of Black and white individuals who banded together to make it through the night. It keeps surfacing for me and I feel it’s time for me to address it.

You wrote a family drama script surrounding two sisters called Big Sister, can you tell us about it and what inspired you to write it?

Big Sister is a feature drama in the vein of Blue Jasmin and August: Osage County. A successful woman abandons her career to save her destitute younger sister, but her efforts backfire and she becomes the one who needs to be saved.

I was struggling to process two tragic events that befell my family. And then, as strange as this sounds, I had a dream that I was having lunch with Julia Roberts. I told her I had a screenplay for her, and she told me to send it over to her agent - then I woke up. I didn't have a script for Julia, even though I wished I did. But two days later, the entire story for Big Sister fell out of the sky. So, reality and fantasy converged, and Big Sister was born! Big Sister has been a competition finalist six times. To date, no producer has picked up the script. However, just today a production company requested it, so, we'll see!

What would you say is an interesting writing quirk you have?

I will write a little bit, and then, “runaway” to social media for a bit, because things get too emotional for me and I feel overwhelmed. But then I “run back” because I know I must “face my fear.” I would say it’s like an odd dance one might do with a romantic partner. You want to dive in, but you try to keep one toe on shore. Finally, it’s like, “It’s all or nothing!” And then I take the deep plunge and don’t surface till I finish!

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Who are some of your favorite screenwriters?

Alan Ball (American Beauty), Jordan Peele (Get Out), Susannah Grant (Erin Brokovich), for starters.

When you hit "Fade Out" on a new screenplay, how do you celebrate?

I’m a pretty good cook, so I whip up something special for myself and my partner. And if I’m feeling extra special, I’ll break out the champagne!

Besides writing, what other skills would you think a screenwriter should have?

Great question. A screenwriter should really have great researching skills. In other words, screenwriters must be willing to go out of their comfort zone and immerse themselves in worlds they are unfamiliar with. I’d also say a screenwriter absolutely must have some level of public speaking skills. If they are going to successfully pitch their work, they must speak clearly and with confidence. This is essential. Also, I really think people should think about their personal appearances. Everyone’s gotten very casual with Zoom, and I understand that, but, make an effort to show up looking your best; I think it makes a difference.

How do you balance your personal life and writing?

I don’t! I can’t find a good way to do it. But mealtimes and “movie viewing” time are sacrosanct, so I do my best to make sure I get my writing in between all of that. But I still want an extra 12 hours a day!

Who is your go-to person when you’re ready for fresh eyes on your script? Why are they your go-to person?

If I must choose one person, I’d say that one of my female colleagues is who I turn to first. She is honest without being cruel. She picks up on things I didn’t even think of. And she offers great suggestions on how to fix or elevate troublesome spots. She, too, is a screenwriter, but she started as a lawyer. I love working with people that came to screenwriting later in life, because they have real-life experience, which helps to ensure that stories are grounded.

Who was the person that influenced your foray into writing?

Sy Dukane. He wrote for the top sitcoms of the ‘90s. He read my first script. He was merciless, but I learned so much. He also thought I was insane to try and get into the business later in life. That just fueled my desire to work harder until I could get something produced. Took me a while, but I got there.

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If you had the power to make changes in the screenwriting industry, what changes would you make?

I would stop the focus on tentpole movies, superhero movies, reboots, and remakes. I would put the focus back on smaller stories about real people who overcome challenges in their personal lives and make the world better for themselves and their loved ones. We all need popcorn movies, yes, but I feel we are losing touch with our humanity.

Where do you hope to see yourself in this industry in the next 5 to 10 years?

I want to be working at the top level as either a screenwriter or a showrunner for one of my series concepts. Mainly, I want to be a working writer with a few heavy-duty credits under my belt.

What is your favorite script you have written thus far and why is it your favorite?

Another great question. I will say Tillie, which is an adaptation of a novel set in the 1890s in Pennsylvania Dutch Country, a world ruled by clannish religious groups and tradition. I had nothing in common with anything in that world – except the main character. She is someone who has been repressed, beaten, tyrannized, and told what she can and cannot be in life. My cowriter and I “got” her and we felt compelled to bring her story to life. I’m really proud of the work we put into it. Tillie shines.

What is next for you?

To date, I have written eight Lifetime style features, all produced. I currently have two treatments I am working on with hopes of them being approved to go to script. But once those are done, I am returning to my passion projects: two female-driven dramas, one set in the 1960s, one in the 1970s, deeply influenced by the music of the day. 


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