Chicago Screenplay Awards Questionnaire

Jess Gupta

Who are you and where are you from?

My name is Jess Gupta and I’m from Omaha, Nebraska.

Where and when did you come up with the idea for your screenplay?

Our second daughter had just been born and I was toying with writing a feature script about a stay-at-home father character. I was also interested in the concept of two people in a confined space, one of whom is sort of terrified of the other, and how to develop that into a full feature. ‘Guardian’ is the result of that.

Can you take us through your screenwriting process?

Concepts and premises come and go, but I’m most excited about projects where I can clearly see the second act and what might happen there. If I get a feel that I have something that can hold an audience’s interest for a full 90 minutes (at least) then I start developing character sketches and an outline and just keep refining it from there. I like the structure of genre films, but also finding ways to subvert audience expectations.

What made you want to become a screenwriter?

I love being in the world of ideas and imagination, and taking creations from that world and grounding them in a written page. I also love movies, especially horror, and you just can’t make a good one without a solid script. A great script can make up for lots of other deficiencies, but I don’t think it works the other way, at least not in my opinion.

Who are your biggest filmmaking influences?

Tony Gilroy is a big influence, along with Michael Mann and David Fincher.

Have you ever been obsessed with a movie or TV show? If so, which one?

Recently, it’s been ‘Servant’ on AppleTV+, which is unlike anything I’ve ever seen. Overall, some of my all-time favorites are ‘The Insider’, ‘Withnail & I’, and ‘The Exorcist’.

What’s your favorite moment in cinema history?

2007 was an epic year for feature film. Contending at the 2008 Oscars were ‘No Country for Old Men’, ‘There Will Be Blood’, ‘Michael Clayton’, ‘Ratatouille’ (animated), along with ‘The Diving Bell and The Butterfly’, which unfortunately fell through the Academy qualifications cracks. I don’t think there’s been such a strong year for features during my adult life.

Who’s your favorite character in cinema history?

Lowell Bergman in ‘The Insider’. He’s a hero who’s sort of relegated to the shadows, and I like those kinds of characters.

If you could talk to anyone from any era, who would it be and what would you ask them?

I feel like history is history, but I would like to go back and speak with my late brother, and ask him to do some things differently. That’s my one regret.

Jennifer Griffith Dunbar.

Who are you and where are you from?

My name is Jennifer Griffith Dunbar. I’m originally from San Francisco; I’ve lived in NY, Madrid, Seattle, DC, and now make Boulder, CO, my home.

Where and when did you come up with the idea for your screenplay?

I wanted to write something fun that was set in a place where I wish I could go right now: Italy’s Amalfi coast. I attended an all-girl school much like the one depicted in the script. The idea of a washed-up tennis star came to me one day and then I thought that seeing her start from scratch at her old school would offer comic potential.

Can you take us through your screenwriting process?

I write one to two scripts per year, workshopped with my weekly writer’s group. I tend towards dramedies and accidental thrillers.

What made you want to become a screenwriter?

I was home with three little kids (my husband is a pilot) and couldn’t finish a novel I had started. When I heard Callie Khouri used Syd Field’s book to write Thelma and Louise, I dared myself to do the same thing with my first script. I enjoyed it so much, I’ve been doing it ever since.

Who are your biggest filmmaking influences?

Woody Allen, Noah Baumbach, John Hughes, Nancy Meyers, Kenneth Lonergan, Tom McCarthy, the Coen Brothers, Lynn Shelton, Michael Arndt, the Duplass Brothers, Tony Gilroy, Mike White, Michael Showalter, Greta Gerwig, Nicole Holofcener, Charlier Kaufman, Jill Solomon.

Have you ever been obsessed with a movie or TV show? If so, which one?
Too many to name but I’ve seen Annie Hall, You Can Count on Me, all of John Hughes Movies, and The Bourne Identity too many times. Search Party has been my most recent binge-watch/obsession.

What’s your favorite moment in cinema history?

When Audrey Hepburn dominated!

Who’s your favorite character in cinema history?

Annie Hall or Ferris Bueller

If you could talk to anyone from any era, who would it be and what would you ask them?

I would want to talk to John Hughes to ask about his inspirations and how he was able to nail the details of so many life stages with so much humor and grace.