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Review: INTO THE WOODS at SF Playhouse

Into the Woods continues through January 17th, 2025.

By: Nov. 28, 2025
Review: INTO THE WOODS at SF Playhouse  Image

Sondheim fans rejoice! We have not one, but two sensational productions to satisfy that itch for smart lyrics and equally solid books. Shotgun Players is running their fabulous Sunday in the Park with George, and now Director Susi Damilano and SF Playhouse have outdone themselves with a stunning Into the Woods. Every component of this production is a winner; casting, technical, and musical.

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The Narrator (Matt Kizer) looks on as Cinderella (Jillian A. Smith) is belittled by her Stepmother (Heather Orth), Florinda (Rachel Fobbs), and Lucinda (Callahan Gillespie).

Leave it to Sondheim to create a story rich in our universal fascination with the fantasy of fairytales, yet deeply rooted in very human behaviors. With a book by James Lapine, Sondheim proposed a mashup of several Brothers Grimm fairy tales with characters taken from “Little Red Riding Hood,” “Rapunzel,” “Cinderella” and “Jack and the Beanstalk” amongst others. From the original story of “Rapunzel” comes the quest of a childless baker and his wife in their quest to start a family, a witch’s curse, and their interactions with other storybook characters.

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The Baker (Phil Wong) shares a moment with his wife (Ruby Day).

Act One is a complete musical in and of itself. The characters are introduced, and their individual wishes made clear; Cinderella of course wants happiness and her Prince Charming, the Baker and his wife want a child, and Jack and his mother, prosperity. By the final scene, all is resolved and everyone will live happily ever after. It includes beautiful songs like “Giants in the Sky,” “Agony,” and “It Takes Two.”

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A wolf (Trevor March) appeals to Little Red Riding Hood (Olivia Hellman).

But this is Sondheim. Act Two delivers his skill at dissecting human emotions both positive and negative, so he introduces infidelity, lust, greed, murder, and revenge- the dark side of Grimms’ tales. Grief and loss, the perseverance of mortals over evil and in the end, loyalty and family are exalted. One can hear borrowed melodies from 1979’s Sweeney Todd in "No One Is Alone" and “Children Will Listen” executed wonderfully by an ensemble cast and the musical direction of Dave Dobrusky.

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The Witch (Alison Ewing) considers the repercussions of her transformation.

Damilano once again proves she’s one of the Bay area’s finest directors. Tiny flourishes like having Indigenous narrator Matt Kizer open the show with a spiritual offering and using two wolves in the Red Riding Hood scene. She assembles a cracker jack technical crew with longtime companion Nicole Helfer’s choreography, Heather Kenyon’s mystical forest set, Christian Meja’s lighting, Kathleen Qui’s marvelous costumes, and Dan Holland’s creepy sound design.

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The cast of San Francisco Playhouse's "Into the Woods.

And what a cast! Sixteen strong, talented actors and singers competent is both drama and comedy. Two giants of Bay Area theater Phil Wong and Ruby Day shine as the Baker and his wife. Alison Ewing makes the witch both terrible and human. William I. Schmidt (Jack), Jillian A. Smith (Cinderella), and Heather Orth (Cinderella’s Stepmother) share the lead roles. Maureen McVerry makes for a hilarious Milky White in white ruffles and pink tassels as udders.

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Jack (William I. Schmidt), The Baker's Wife (Ruby Day), and Jack's Mother (Eiko Moon-Yamamoto) try to milk the cow Milky White (Maureen McVerry

Into the Woods may be Sondheim’s most accessible work, appealing to the child in us all. It takes us from youthful innocence to adult sensibilities and harsh realities; with the hope we’ll be stronger and wiser.

Into the Woods continues through January 17th. For tickets go to sfplayhouse.org or by calling (415) 677-9596.

Photo credits: Jessica Palopoli

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