Star-studded cast announced for Will Rogers-inspired Oklahoma film

Oklahoma’s rich history is heading back to the silver screen with a major new Hollywood production, and it has officially found its star-studded cast.

According to an exclusive report from Deadline, The Lord of the Rings star and SAG-AFTRA President Sean Astin is set to star alongside Emmy winner Jeremy Piven (Entourage) and Oscar nominee Lorraine Bracco (The Sopranos) in the upcoming high school sports drama, Will to Win.

The film is making history as the very first movie project to be officially endorsed by the family of early Hollywood icon, Cherokee Nation citizen, and “Oklahoma’s Favorite Son,” Will Rogers.

The Story Behind Will to Win

The movie—which is currently filming on location in Oklahoma and Vancouver, British Columbia—is adapted from the book by author Jim Stovall and directed by Sean McNamara (Reagan).

The drama centers on a young Chickasaw softball player, played by Isabel DeRoy-Olson (Three Pines), who faces an uphill battle after moving to a new high school with no softball team. Determined to play, she joins the boys’ baseball team with the support of a compassionate coach (Astin).

Her spot on the team is quickly threatened by a school board president (Piven) determined to remove her. To help navigate the challenges, the young athlete begins having vivid, imaginary conversations with Will Rogers himself, who guides her through life’s hurdles using his signature wit and wisdom.

Keeping it Local and Authentic

The production features strong local ties and a deep commitment to Native representation. Tulsa-based Kirkpatrick & Kinslow Productions is producing the film alongside Brookwell McNamara Entertainment and in collaboration with Chickasaw Nation Productions.

Acclaimed Comanche filmmaker Jhane Myers (Prey, 1883) serves as an executive producer, while Indigenous actress Stefany Mathias (Prey) joins the cast as the young girl’s grandmother.

For the family of Will Rogers, endorsing a film for the first time was all about keeping his legacy alive for a new generation.

“While we have been approached many times in the past about producing movies, this is the first time the family has endorsed a movie project,” Will Rogers’ great-granddaughter, Jennifer Rogers Etcheverry, told Deadline. “We are thrilled to see that audiences in the 21st century will learn about the impact of Will Rogers on the world.”

Keep an eye out for updates on local release dates and production highlights right here on News on 6.

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