Iconoclast director Matthew Frost has a flair for meshing style and humor, as seen in previous projects for Viva Vena, starring Lizzy Caplan and for Vogue, including a recent film that captured a vulnerable Kate Winslet. The latter was the first of his series of shorts with the fashion magazine, which has tapped him to add dimension to its celebrity cover models via film.

The latest features Jessica Chastain sitting on a park bench like your everyday person -- but not like your everyday person, since she's an A-list star. Which, of course, means she's subject to the gawking and fawning of fans. Mr. Frost illustrates that reality of celebrity life with wit, showing how Ms. Chastain addressing a stealth admirer head-on.

"I love the faces people make when they're texting or looking at their phone -- I always have the feeling that maybe 1% are doing something that matches the facial expressions they're letting off," he explained of the concept. "I liked the idea that [Jessica] would be trapped in the middle of one of these silent conversations. I was curious to see what it looked like when a hyper-aware and present actress who knows exactly what's going on around her gets confronted with that. I'm sure it happens to her all the time so it's fun to try and recreate it in a silly way."

Mr. Frost has a third film in the works with another top talent to be featured on a future Vogue cover. All the shorts feature the actresses as themselves, and Mr. Frost came up with the scenarios. "The concepts all mine and Vogue has been very open to it, which has made it a lot of fun."

But the success of the films also relies heavily on the stars' talent. "[I'm] asking these actresses to basically do the thing that they do best, that they are very serious and passionate about," said Mr. Frost. "This allows the humor to always be based on some kind of dramatic tension. Their ability to make something immediately cinematic and legitimate is something that's fun to play around with. The fact that I'm there in a position to execute these silly little ideas with these high-caliber performers is part of the what the idea leans on. It's two very different worlds coming together, and I just like to try and capture a side of them that's a bit different, that feels genuine and randomly relatable."

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