Schoolhouse Theater: A 40th Season with Jazz, Scandal and Mishaps

Inside an intimate 100-seat theater, a lone trumpet announces a legend of the jazz scene as the curtain rises on Satchmo at the Waldorf. The one-man show’s star, Wali Jamal, warns of the production: “There’s no fourth wall. I’m taking it off to the audience, and there’s just no protection — for you or for me.”

The show kicks off the Schoolhouse Theater’s milestone 40th season. The team at Schoolhouse chose this production not only to honor jazz legend Louis Armstrong, whose nickname was Satchmo, but to set a tone of ambition and emotional depth. “When you think about what made the American 20th century, it was jazz,” says Producing Director Bram Lewis. “And when you think about jazz, you think of Louis Armstrong.”

Bringing Satchmo to the Stage

Satchmo at the Waldorf, based on a book by playwright and former Wall Street Journal critic Terry Teachout, premiered in 2009, running Off-Broadway for a year. “As far as I know, there hasn’t been a production of Satchmo in about a decade,” Lewis explains. Determined to bring this story back to life, he embarked on a three-month casting search that spanned Louisville, Cincinnati and New York. “I hit the jackpot when I found Wali Jamal,” says Lewis.

Jamal is an award-winning actor and the only one to have done all ten plays of August Wilson’s American Century Cycle. He credits his stand-up roots for his ability to carry the show. “Comedy prepared me,” he reflects. “Learning an hour of material in stand-up taught me to swallow a script whole.” As both narrator and performer, Jamal plays three distinct characters at once: Louis Armstrong, his manager Joe Glaser and the legendary Miles Davis.

“There’s some really funny moments in it that’ll split your sides with laughter,” Jamal promises, “and some moments that’ll just rip your heart right out of your chest.”

Under Lewis’s direction, Satchmo traces Armstrong’s journey, which he describes as a breathtaking story of someone who grew up in “hard poverty in New Orleans… [but] had no chip on his shoulder.” It doesn’t shy away from racism or personal struggle yet balances heartbreak with humor as it tells of Armstrong’s rise to global stardom.

40 Years of Schoolhouse Theater

After Satchmo, Schoolhouse pivots to an older tale that still packs a punch in 21st-century Westchester. In September, they’ll stage Les Liaisons Dangereuses. The theater’s artistic director, Owen Thompson, who will direct the show, teases, “It’s France in the 18th century, so it’s sex, scandal and sword fighting.”

Later, in December the final production of the 2025 season, Jeeves and Wooster in Perfect Nonsense, arrives—a fast-paced, Olivier Award–winning comedy in which the fictional character Bertie Wooster’s attempt at a one-man show ends in uproarious mishaps.

Lewis sums up the season’s variety: “There’s no one on earth like Louis Armstrong. And then we shift and go into a costume drama that’s dark and sexy like Les Liaisons, and end up with ‘perfect nonsense’ in Jeeves and Wooster.”

Schoolhouse, which Thompson says is the oldest professional theater company in Westchester, has weathered COVID and even the loss of its founder, Lee Pope. “Passion and stubbornness have been the key to our success,” he reflects. Lewis adds another ingredient: ambition.

While it’s many people’s impulse to travel into the city for quality theater, Schoolhouse remains a hometown treasure where every seat feels like a front-row experience. Lewis points out that “you can walk to the theater from the train station, so it’s easy to get to, but people have to pay $200-400 to see the same award-winning actors down in New York.” Thompson adds that at Schoolhouse, ticketholders who attend all three shows get a 20% discount, “so you’re getting three shows for less than the price of one ticket to a Broadway show.”

Even in an intimate theater like the North Salem Community Center in Croton Falls, the Schoolhouse benefits from what Lewis and Thompson boast as a top-tier crew: A lighting designer with 60 Broadway credits, a set designer whose paintings have hung in Berlin and Tokyo, and a costume designer who made Jamal feel sharp in his Satchmo tux all make sure that these intimate productions shine.

From the soulful notes of jazz to the wit of classic comedy, it’s curtains up for Schoolhouse Theater’s 40th season.

For more arts news and updates, visit artsw.org/artsnews.

About Scott Meaney

Scott Meaney is a writer based in Mt. Kisco, New York. He has written for numerous publications, including ArtsNews, Dualshockers, Comic Book Resources and various newspapers. He also has been an SEO copywriter for 11 years.