Andrew Keenan-Bolger to Lead Character Development Masterclass at Westport Country Playhouse

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The NEWSIES originator will lead separate sessions covering fundamentals for younger actors and advanced text analysis for experienced performers.

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Westport Country Playhouse will present a masterclass with actor Andrew Keenan-Bolger , best known for originating the role of Crutchie in Disney's “Newsies” on Broadway. Titled “Building Characters from the Inside Out,” the interactive masterclass will give participants an opportunity to explore the craft of character development through monologue work, script analysis, and imaginative storytelling.

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The masterclass will take place on Sunday, September 20, from 11 a.m. to 1 p.m. for middle school students (grades 6-8), and 2 to 4 p.m. for high school students (grades 9-12).

“Andrew is one of those rare performers who brings enormous talent, warmth, generosity, and a genuine love of the craft to everything he does,” said Ben Frimmer , a member of the Playhouse board of trustees and teacher of theatre arts for the Westport Schools. “From Broadway to television to his work as a director and writer, he has had an extraordinary career—and he's an amazing teacher and mentor.

This is a fantastic opportunity for young performers to spend time learning from someone who has truly been there and done it at the highest level.”

Through hands-on coaching and practical exercises, Keenan-Bolger will share the tools he uses as a working professional to transform words on a page into dynamic, memorable performances. Whether preparing for auditions, school productions, or simply looking to strengthen their acting skills, participants will leave with greater confidence, a deeper understanding of character development, and techniques they can apply to any role.

The middle school session is designed for younger actors, introducing the fundamentals of character creation in a supportive, energetic environment that encourages creativity, collaboration, and confidence.

The high school session is geared to more experienced performers, taking a deeper dive into text analysis, character choices, and the nuances of monologue performance, with individualized coaching to help actors elevate their work.

Andrew Keenan-Bolger 's credits include: Broadway: Crutchie in “Newsies” (Outer Critics Circle nominee), “Tuck Everlasting” (Drama League Award nominee), “Mary Poppins,” “Seussical,” “Beauty and the Beast,” “A Christmas Carol”; Off-Broadway: “Dracula: A Comedy of Terrors,” “Titanique,” “Scarlett Dreams,” “Seven Deadly Sins”; TV: “The Undoing,” “The Blacklist,” “The Other Two,” “The Marvelous Mrs. Maisel,” “Nurse Jackie,” “Looking”; Film: “On Swift Horses,” “The Rewrite,” “Marci X”; Co-creator of “Submissions Only”; Co-author of the book series “Jack & Louisa,” and author of the YA novel “Limelight” (Penguin). @KeenanBlogger

The fee for the masterclass is $100, and is limited to 15 participants per session. Scholarships are available. For full details and registration form, visit: https://www.westportplayhouse.org/masterclassseries/

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_Originally reported by [BroadwayWorld](https://www.broadwayworld.com/connecticut/article/Westport-Country-Playhouse-to-Host-Masterclass-with-Andrew-Keenan-Bolger-20260911)._