Q&A: Frank Whaley on the Unlikely Friendship at the Heart of ‘Like Sunday, Like Rain’

When Eleanor (Leighton Meester) loses her waitress job and dumps her cheating boyfriend (Green Day’s Billie Joe Armstrong), she unexpectedly lands a live-in nanny gig with an unusual charge: 12-year-old musical prodigy Reggie, whose mother (Debra Messing) is extremely wealthy… and not much of a mother. As Eleanor and Reggie (newcomer Julian Shatkin, wise beyond his years) test each other’s boundaries, secrets emerge, and gradually they forge a tender and unlikely friendship. Actor Frank Whaley moves behind the camera for Like Sunday, Like Rain, which illuminates the wondrous serendipity of life in New York City. 


Please describe Like Sunday, Like Rain in your own words.

Frank Whaley: Like Sunday, Like Rain is a story about two people from two completely different ends of the universe. Through a random set of circumstances, they enter into each other’s lives and become friends. It’s a love story, but more to the point, a story about love, and our longing and struggle throughout our lives to find it.

Reggie is a 12-year-old cello prodigy who lives in an opulent home on the Upper West Side of Manhattan. It would appear as though he has everything he could possibly want in his life, however he is essentially alone in the world. Eleanor is a young woman who is drifting through life with a deep sadness and loneliness. When these two find each other they discover the element that has been missing within both of them.

As the writer/director, what inspired you to tell this particular story?

FW: I drew a great deal of inspiration for Like Sunday, Like Rain from New York City, where I lived for almost thirty years. I was always fascinated by how many different people and lives, from so vastly different backgrounds and socioeconomic stratospheres, randomly collide on a moment to moment basis there.

I also find great interest in the subject of childhood, and the loneliness and feelings of isolation and hopelessness that can sometimes accompany it. Moreover, as is the case with Reggie, and to a certain degree both characters in the story, I’m intrigued by the subject of children who have had to fend for themselves from a young age in order to survive.


Let’s talk about Leighton Meester, who has tackled Broadway (“Of Mice and Men”) and several acclaimed indies since becoming a star on “Gossip Girl.” What spark did you see in her that convinced you she could be Eleanor?

FW: I first became familiar with Leighton Meester from her work in the film Country Strong, just around the time I was finishing the first draft of Like Sunday, Like Rain. Something about her performance stayed with me, how striking she was but at the same time so relatable on screen. She seemed to be carrying a great deal of history for someone so young. Leighton has such poise and grace, but also a certain vulnerability that escapes through her eyes.

When we met for the first time, I knew the moment I sat down across from her that she was Eleanor. We talked for hours about the script and it occurred to me that she knew more about the character and her world than I did. It was immediately clear to me that she understood the nature and makeup of this character. There was never anyone else.

And you’ve captured lightning in a bottle with young Julian Shatkin, who appears poised to break out at any moment. How did you discover him?

FW: A studio executive once told me that he loved the story and the script, but I would never find a 12-year old capable of playing Reggie. The casting director brought in many established and talented young actors, but none of them could fully understand the complexity of the role, or they played at the “nerdy” aspects of what they perceived Reggie as being. The tricky thing about the role is the dual aspect of it. Reggie is at once a little boy, but then in an instant a grown man. Reggie is charming, streetwise, and savvy, but also possesses a brilliant mind. It was necessary for the actor playing this character to find a way to portray all of those elements and make him likeable. At a certain point during the casting I began to wonder if perhaps my studio executive friend was right. And then Julian Shatkin walked in.

The moment he began to say the words, I believed he was this person. His natural inclination was not to do too much. He took direction and made subtle adjustments. He moved everyone in the room to tears.

Though you’ve directed several features, your acting filmography continues to grow as well (I loved [the unfairly underseen] Rob the Mob, and your cameo on “The Blacklist”). In working with a cast, do you think acting makes you a more insightful director?

FW: I have been working as an actor for close to thirty years. That experience has helped me not only to understand the nature of acting, and how to build a strong performance, but I believe it has given me a firm grip on the nature of filmmaking.

I’ve had the opportunity to work with some of the greatest directors of our time, including Quentin Tarantino, Oliver Stone, Phil Alden Robinson, Rick Linklater, and John Woo, to name a few. It’s impossible not to learn when you are exposed to that caliber of talent. I made a point early on to watch closely and learn, not only from the great ones, but also from the less experienced and first time directors. Being on hundreds of film sets as an actor has proven to be an invaluable practical experience.


What do you want audiences to take away from Like Sunday, Like Rain?

FW: I want audiences to walk away from Like Sunday, Like Rain feeling happy that they spent 104 minutes with these two people. I hope for some the experience is akin to having finished a good novel, where the characters and story stay with you as though you had actually lived it with them.

What are you most looking forward to at the 2014 Hamptons International Film Festival?

FW: I’m looking forward to sharing Like Sunday, Like Rain and interacting with the Hamptons International Film Festival audience. I’m excited to hear their thoughts and reactions to this story. I’ve been to the HIFF in the past as an audience member, and have always found the atmosphere exciting and stimulating. It has long been a goal of mine to be invited to participate as a filmmaker. I’m thrilled and honored to be a part of it with Like Sunday, Like Rain.

Like Sunday, Like Rain will have its East Coast premiere in the World Cinema section at HIFF 2014.

Frank-WhaleyLike Sunday, Like Rain marks Frank Whaley’s fourth feature film as a writer/director. His first, Joe the King, premiered at the 1999 Sundance Film Festival, where it earned Whaley the Waldo Salt Screenwriting Award. His second, The Jimmy Show, premiered at the 2002 Sundance Film Festival. In 2007 Frank wrote and directed New York City Serenade, which made its premiere at that year’s Toronto International Film Festival. Whaley is also a critically acclaimed actor, having appeared in over 75 film and television productions, including iconic films such as Pulp FictionField of DreamsSwimming With Sharks, and many others.