2025 Woodstock Film Festival: A Conversation with Actor Michael O’Keefe

Continuing our ongoing 2025 Woodstock Film Festival interview series, we recently caught up with actor and Hudson Valley local, Michael O’Keefe. Michael stars in the film A Break in the Rain, which has its world premiere at the festival this year. It was filmed in Upstate New York in 2024, and the cast features Michael O’Keefe, S. Epatha Merkerson, Emily Donahoe, Will Chase, Mary Beth Peil and Elizabeth A. Davis. A Break in the Rain, directed by Don Scardino, is a film about grief, resilience and the human connection.

Michael O’Keefe is a film, television, and stage actor known for his roles in the films Caddyshack and The Great Santini, the TV series Roseanne, Homeland, and most recently, Your Friends and Neighbors on Apple TV. Michael received an Academy Award nomination for Best Supporting Actor for his role as Ben Meechum in the The Great Santini.

Read our exclusive interview below for more about the film and Michael’s role in it.

For tickets to the October 15th screening followed by Q+A and a live performance by “The Catriona Walsh Band”, click here. 

INSIDE+OUT: Tell us about the film, A Break in the Rain. What does it mean to you to have this film featured at the festival, and what impact or message do you hope it leaves with the audience?

Michael O’Keefe: I love our movie a great deal. It means the world to me to be in the Woodstock Film Festival because of its prestige, and because I live in the Hudson Valley.

The audience for A Break In The Rain will experience a kind of healing journey akin to the journey the two lead characters embark on. My character learns what it means to grieve loss and stay connected to family. Catriona discovers that having a child and being a touring musician is not only possible, but a powerful way to express yourself in the world, and engender familial bonds.

Was there a defining moment or influence that led you to the film industry, and how has that shaped your journey?

Michael O’Keefe: When people ask me why I became an actor, I often say, “Because my parents dropped me as a child.”

On a more serious note, I owe a large part of my career to the inspiration of Pat Conroy, the novelist. I was fortunate to play his alter ego, “Ben Meecham,” in The Great Santini. Had Pat not made the journey from child of an alcoholic to artist capable of transmuting that trauma into literature, I’m not sure I would have ever had the career I have, nor would my work have the same kind of emotional depth. Along with him, I owe another debt to Robert Duvall, who played my father in the film. His commitment to authenticity is exemplary. Bobby was a great scene partner and inspiration.

Can you share a memorable moment or story that stood out for you while working on this film? Any funny or crazy story that happened before filming or while on set?

Michael O’Keefe: The most eye-popping moment for me during filming was hearing Elizabeth Davis sing live and play fiddle for the first time. She’s world-class, and I remember seeing her at The Falcon in Marlboro, NY where we filmed the first music scene, and being knocked over by her talent.

As technology continues to transform how stories are made and shared, where do you see the biggest opportunities or challenges for creators?

Michael O’Keefe: Like the music business had to adjust to synthetic instruments, we will have to adjust to AI and CGI as filmmakers. They both have their place, but I contend that there is no replacement for a heartfelt performance or the kind of stunts Tom Cruise does in the Mission Impossible movies. Putting yourself on the line gives the audience an immense thrill.

Was there a moment in your career that fundamentally changed how you approach your craft?

Michael O’Keefe: Seeing myself give a lame performance on film made me realize that I had to get busy learning more about the craft of acting, and to continually study it to increase my skill and capacity for nuance. Before she died, I worked with Penny Allen, a fine acting coach, for over twenty years. She challenged me like no one had before to humble myself and become teachable.

When people look back on your body of work, what do you hope they see?

Michael O’Keefe: Someone who took the art form seriously and served the stories being told.

What is your current state of mind?

Michael O’Keefe: Despite the turmoil of the times, I am hopeful for the future of the world and the future of filmmaking. Like Martin Luther King, Jr., I believe the long arc of history bends toward justice, which gives me hope. And, I think every generation that has followed mine has a plethora of great talent and genius. Films are forever, in a way. I hope they continue to enlighten and entertain.

Photos courtesy of Painted Guitar Pictures

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About the Woodstock Film Festival

The 26th Annual Woodstock Film Festival brings a slate of distinguished films to screen from October 15 to October 19, 2025, at venues across the Hudson Valley towns of Woodstock, Rosendale, Kingston and Saugerties.

Founded in 2000, the Woodstock Film Festival (WFF) is a not-for-profit 501(c)(3) organization that nurtures and supports emerging and established filmmakers. WFF provides innovative mentoring and inspired educational programs benefitting filmmakers, students and diverse audiences while serving as a powerful cultural and economic engine for New York’s Hudson Valley and beyond. Such efforts have consistently resulted in the festival being hailed as one of the top regional film festivals worldwide. 

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Now in its 26th year, 2025 promises to be as exciting as ever. See you there!

 Click HERE for this year’s full line up + film guide

Click HERE for schedule and tickets