Jessica Caldwell’s “Billions”

As the Westport Country Playhouse reaches out to younger audiences, a new generation of trustees has joined its board.

One name is familiar: 24-year-old State Senator (and 2014 Staples High School graduate) Will Haskell.

Jessica Caldwell is not as well known. But she has a fascinating back story, one that serves her well in her role helping oversee the 90-year-old theater.

Raised in a lobstering village of 500 people off the coast of Maine, and just 16 when she headed to college, Caldwell took screenwriting, writing and communications courses as an undergrad.

Jessica Caldwell

That led to Columbia University’s MFA program, from 2009 to ’12. She went on to produce independent feature films (“Electrick Children,” “Happy Baby,” “AWOL”). and the upcoming “When I’m Done Dying.”

Her feature films have premiered at Berlinale, SXSW and Tribeca. Her short films were shown at Sundance, Telluride and Tribeca.

She’s had a hand too in TV. After hearing Brian Koppelman and David Levien speak while still in school, she connected with them on social media. When they needed an assistant for a new show called “Billions,” they hired the 26-year-old Caldwell.

She worked in the writer’s room and as a showrunner — both in assistant roles.. It was an “intensive crash course, with amazing actors and a great network.” The experience was both exhausting and exhilarating.

“Billions” was set originally in Westport. The hedge fund was modeled in part on Bridgewater. Caldwell did not yet live here. And she was not yet married to her husband — who coincidentally now works for a local hedge fund.

“Billions”‘ Axe Capital hedge fund was originally set in Westport.

Koppelman and Levien encouraged her to write full time. She’s written features and book adaptations, and helps develop ideas for production, like “Gonzo Girl.” A first-person story about a bizarre first date got plenty of New York Times attention.

“I keep trying to roll the ball forward,” Caldwell says. “You never know what people will want.”

The pandemic changed how she works. Pitches were done entirely on Zoom, with executives in Los Angeles and producers in London.

It was a tough time for feature films. But the rise of platforms like Disney+, Paramount+, Apple TV+ and Peacock filled people’s needs for entertainment options. “We’ve all had to think on our feet and adapt,” Caldwell notes.

She is thankful to have a place like Westport to write in (and, with her husband, raise their year-old son).

Living here has brought her to the Playhouse, too. She first volunteered for the annual gala; the more she saw, the more she realized she could help reach out to younger audiences.

New trustees will help the Westport Country Playhouse reach younger audiences.

She looks forward to mentoring younger members of the arts community. She is thankful for the help Koppelman and Levien gave her, early in her career, when “Billions” was just starting out.

And when the only reason she knew Westport was through the fictional world of its Axe Capital.

2 responses to “Jessica Caldwell’s “Billions”

  1. Such and interesting story and I’m sure Jessica will go on and have many successful productions. But bear with me for a short story. ( No pun intended.) In high school, I could never get over a C+ in writing. But I used to shoot pool with a guy around 1962 and 1963, who grew up in a ranch house on the corner of Long Lots and Bayberry La. In 1966, in college, I asked him to help me in my college Creative Writing class. I got an A in that class! I lost track of him around 1968. But 14 years, after he got me that A in Creative Writing, he wrote a story, sold it to one of the big movie production companies, and the movie made 75 million! There were sequels to the original movie too. I actually googled him this week because I want to reach out to him to say hello. I found out he owns a production company out in Encino, California. Anyone who was in Westport back then knows exactly who I’m talking about. I’m sure Jessica would love to meet him too. They would have a lot in common.

  2. Fascinating backstory. And a wonderful choice to help the Playhouse in the coming decade.

    Re bringing in younger audiences: borrowing from tonight’s offering at The Remarkable Theater, I have three words for you: “Cambodian Rock Band.”

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