By: Ashley Ann Wolfe

March 23, 2022

“It never hurts to keep looking for sunshine.”



When live theatre performances began returning to the stage, I had the great privilege of attending a plethora of plays and musicals. Some of the best art in generations is being created right now and, after 18 months without a show, I decided to make up for lost time. Between New York and Chicago, I attended nearly every new play and musical thus far this season, and it truly is a season of riches. While I tend to lean toward the dramatic, I caught wind of a new musical bringing cheer to Theatre Row, and that’s how, on a blustery Saturday morning in November, I found myself, a solo adult woman, rushing to make a 10:00am curtain of Winnie the Pooh.

Turns out, I wasn’t alone. The performance I attended had an audience of approximately 60% people with children and 40% adults of all ages: clearly the desire for this tale spans generations. I love a story with a statement, and what better statement to impart on kids (of all ages) than the philosophies shared in the Pooh universe. These philosophies, as it turns out, speak to what Americans are telling us they want. Through the Culture + Community in a Time of Transformation national study, we learned that the top four feelings people want more of in their life are “fun”, “calm”, “adventure”, and “connection.” In advance of the Winnie the Pooh musical now opening in Chicago, I asked producer Jonathan Rockefeller, founder of Rockefeller Productions, about the challenges of making theatre during this time and how this story specifically speaks to, and provides, the very feelings folks are hoping to evoke more of in their lives right now.

Ashley: Congratulations on the success of the New York run of Winnie the Pooh and thank you for taking the time to answer a few questions in advance of the Chicago transfer. I’m thrilled that my home city will experience the joy that I saw this fall. Pooh has been a beloved character for nearly a century; however, I was struck by how the story felt nostalgic and familiar yet still new and fresh. Can you speak to the challenges of creating an original musical from source material that is so well-known? What drew you to Winnie the Pooh, and how did your team approach envisioning a new story for the stage while remaining true to the characters’ origins?

Jonathan Rockefeller: It’s a tremendous honor to have the opportunity to approach such a revered and beloved character and put our own spin on him. Part of our daunting challenge was to honor the deep bench of Winnie the Pooh materials – both from the original A. A. Milne book and over almost six decades of the great Disney adaptations, including the infamous Sherman Brothers music. At its core, Pooh is ultimately a heartfelt collection of stories about friendship, adventure and innocence with a youthful spirit. A fresh adventure that contains those ideologies was always important to create something for the young and the young at heart.

Ashley: What made you choose Chicago as the next home for the Hundred Acre Theatre, and are there plans to visit other cities?

Jonathan: Chicago is a wonderful, wonderful place for good theatre. But truthfully, Tigger just wanted to try deep dish pizza. He said, “it’s what Tiggers love da best!” Yes, not just cities, but other countries too! “You can’t just stay in the forest and wait for people to come to you; you have to go to them sometimes!”

Ashley: Immediately upon entering the Hundred Acre Theatre, I was washed over with a sense of calm and welcoming, and the ambience remained throughout the experience. From the inviting carved wood signage to the cerulean sky and chirping birds that greet audience members as they enter the house, the design and aesthetic is that of a safe, calming space. The sense of joyful calm carries even to the merchandise (well-done!). Can you talk a little bit about the design process and how these elements – from set to score to puppets – came together so successfully?

Jonathan: We believe that everything in the DNA of Winnie the Pooh is about ‘joy’. You express it so wonderfully in your question – the experience of the show. It was our goal from the moment you walked in the door that you, too, are welcome into this new adventure in the Hundred Acre Wood. Nate, our composer, scores our shows like one expects at the cinema. It is a warm guide that elevates the story; and I cannot say enough for our talented team of puppet builders (or ‘Rocketeers’ as we call them). This also includes our plushes, which are modeled on the puppets themselves, so there is a real cohesion of the experience that you can also take home. I have seen many Instagram photos of our merchandise plush getting up to all sorts of adventures after they’ve been to the show.

Ashley: While Pooh absolutely has multi-generational appeal, a large portion of your audience are children who cannot yet be vaccinated. When I saw the production at Theatre Row, I was impressed with the efficiency in managing not only vaccination checkpoints but also covid tests for the young ones. There was even a testing tent available directly outside of the theater for anyone who was not already prepared with a test. How did you approach the logistics of premiering a children’s musical during the time of COVID? Any advice for other theatre-makers on what worked well?

Jonathan: I’m very fortunate to work with a team who is equally as determined as I am. In every instance we wanted to ensure that our audiences, cast and crew felt safe and secure. When mandates came into play, we explored every avenue possible to make testing as stress-free as possible (especially for the young ones). This included convenient and free COVID testing onsite, so audiences could be comfortable and assured in having an enjoyable day in the Hundred Acre Wood.

Ashley: Speaking of safe/calm spaces, something we can all use these days, I love how the new story emphasizes each character’s notably thoughtful qualities, building on the Pooh universe’s tradition of teaching the importance of caring for others, working together to problem-solve, and speaking openly about one’s troubles, while touching on everything from facing fear to supporting mental health. What does it mean to you to bring such crucial messaging to folks, especially children navigating these emotions during a pandemic? What do you hope they take away from the production?

Jonathan: There are so many important messages in the show. But, as Pooh puts it best, “You’re braver than you believe, stronger than you seem, and smarter than you think.”

Ashley: Finally, which Winnie the Pooh character do you most identify with? What traits do you believe make them a great character for a musical?

Jonathan: I do find that I am a bit of a Pooh. Not just because I very much love honey, but I am surrounded by wonderful friends and passionate collaborators. The immense differences between each Hundred Acre Wood character makes for great moments of conflict and misunderstandings. But it’s their ability to accept each other’s differences as they try to make sense of the world and circumstances around them that makes their adventures so rewarding. As Tigger states in-a-very-Tigger-sort-of-way: “Aren’t we lucky to have friends like us?”

We are quite lucky, indeed.

Winnie the Pooh is now running for a limited engagement in Chicago at the Mercury Theater. For more details on findings from the national Culture + Community in a Time of Transformation study, visit our microsite here.

Have you been inspired by a piece of theatre or other cultural experience recently? I’d love to hear from you!

Headline photo: Courtesy of Rockefeller Productions and Carol Fox & Associates

Photo above: Sign and friendly staff welcomed patrons to the Hundred Acre Theatre in New York, November 2021. Photo provided by author.

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