Chicago Screenplay Awards Questionnaire

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.