Students Head “Into the Woods” for Upper School Musical

Take a step into a cautionary fairy tale mash-up that comes to life in the upper school production of Stephen Sondheim’s “Into the Woods” at the Claudia Boettcher Theatre this week.

“The show offers a mix of humor and heart, along with some really beautiful music,” said Meg O’Connor, director/costume designer/puppet designer/choreographer. “And words! The lyrics are so fast and so complex, but careful listeners will be richly rewarded.” 

Senior Sage Weinstock plays the Witch, whom she describes as “a fascinating brew of funny, cruel, suspicious and pragmatic.” 

“The Witch is both an incredibly powerful and scary figure,” Wenstock explained. “She’s stuck, in some ways, as this wounded young woman trying (and failing) to protect Rapunzel (her daughter) from having to face the deceptive and unfair world that she faced.” 

MainStage newcomer Leila Gross ’27 plays Lucinda, one of Cinderella’s evil stepsisters. She said that Lucinda’s wardrobe helped her easily slip into this “over-the-top" role: “We have such an incredible costume team, and they worked so hard at creating the perfect dresses with the most flashy accessories. I'm sure it will get a big laugh during the shows.” 

O’Connor shared that “With a diverse cast, we have introduced costume items that reflect the homes and heritage of our performers and the Masters community. The impulse to tell stories as a means of reckoning with life's hard lessons is a global one, and we wanted to at least give a nod to that in our costuming.”

Musical director Katie Meadows has been working diligently with the students on mastering Sondheim's lyrics and melodies. Some performers have compared the excitement of learning a complex Sondheim score to the intricate work they do with Shakespeare in the spring. Weinstock has embraced the challenge with verve. “‘Last Midnight’ is an incredibly athletic song –– it demands a lot of vocal agility and power,” she said. “I love the complexity and difficulty of the song and I love the narrative and the dynamic extremes.”

According to O’Connor, the hard work of 34 cast members and some 40 students handling production, stage management, costume and scenic design, has been going “incredibly well.” She credits much of that to Peter Wylie, technical director/lighting designer/set designer, and Gilles Pugatch, sound designer/master carpenter. “We're lucky that the faculty artists who are leading students through the project are cross-trained in several disciplines,” O’Connor said.

“Into the Woods” opens tomorrow, Thursday, February 22, at 7:00 p.m. with shows on Friday, February 23, and Saturday, February 24, at 7:00 p.m. in the CBT.

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