STILL CASTING ITS SPELL

Sondheim and Lapine’s fractured fairytales
find fresh magic at San Francisco Playhouse

Stephen Sondheim and James Lapine’s Into the Woods may be one of the most beloved titles in the modern musical-theatre canon, but San Francisco Playhouse’s holiday-season staging makes a strong case for why it keeps earning its place. From the moment you encounter Heather Kenyon’s striking, larger-than-life forest — bright, vibrant, yet shadowed at the edges — the journey feels magical, fully primed for the intricate storytelling.

William I. Schmidt, Maureen McVerry, Ruby Day, Eiko Moon-Yamamoto

First seen on Broadway in 1987, Into the Woods entwines the classic children’s tales of Cinderella, Little Red Riding Hood, Jack and the Beanstalk, Rapunzel, and the Baker and his Wife into a single adventure. In Act I, each character ventures “Into the Woods” in search of something they believe will finally make them whole — love, stability, beauty, a child, escape — confronting their fears as well as whatever witches or demons they may face. Their paths cross-pollinate, collide, and complicate in ways only fairy tales (and Sondheim & Lapine) could orchestrate. (An earlier Sondheim & Lapine opus, Sunday in the Park with George, is wowing at Shotgun in Berkeley).

Phil Wong, Ruby Day

Act II arrives just after happily ever after (“So Happy”), exposing what happens when wishes are granted but consequences follow. The Giant’s widow descends seeking revenge on Jack; Cinderella discovers the limits of a royal marriage; the Baker and his Wife wrestle with parenthood; and the Witch finds that beauty without power is not much of a victory. As things seemingly fall apart in the world, the theme of “No One Is Alone” becomes the underlying message. The forest grows darker, the losses more real, and the surviving characters discover that community — not fantasy — is what ultimately holds them together.

Alison Ewing

At San Francisco Playhouse, the ensemble is stacked with genuine triple threats. Jillian A. Smith is a luminous Cinderella, grounding her sweetness with palpable intelligence. Alison Ewing delivers a riveting Witch — wicked, wounded, commanding, and slyly hilarious whether gnarled or glamorously restored.

Trevor March and Johann Santiago Santos

Ruby Day’s Baker’s Wife radiates warmth and emotional precision, her voice carrying every ambivalence and longing in the second act stunner, “Moments in the Woods.” As the Princes, Trevor March and Johann Santiago Santos charm individually but truly shine together, swaggering, preening, and harmonizing their way through “Agony,” the show’s funniest number.

Matt Kizer, Jillian A. Smith, Heather Orth, Rachel Fobbs, Callahan Gillespie

Comic delights abound thanks to Heather Orth as the Stepmother and stepsisters Rachel Fobbs and Callahan Gillispie, whose brightly costumed malice (boosted by Kathleen Qiu’s designs and Laundra Tyme’s wigs) is deliciously over the top. Olivia Hellman’s Little Red Riding Hood is obnoxious, sweet, and impish in all the right ways. William I. Smith (Jack) and Phil Wong (The Baker) bring sincerity and grounded emotion, anchoring the story’s heart. And Maureen McVerry (Milky White the Cow & Granny) and Eiko Moon-Yamamoto (Jack’s Mother) use sharp physical and vocal choices to make their characters distinctive.

Samantha Rich and Alison Ewing

Christian Mejia’s lighting deepens the visual narrative, drawing shadows across the forest at just the right moments, and Dan Holland‘s sound of thunder and the impending visit of the Giant’s wife enhance the suspense. Nicole Helfer’s choreography keeps the movement crisp and cohesive, while Dave Dobrusky’s musical direction handles Sondheim’s notoriously intricate score with clarity, balance, and buoyant humor.

Trevor March and Olivia Hellman

Director Susi Damilano brings all of these elements together with care, pacing the story with emotional transparency and trust in the material. Her ability to highlight character humor while sustaining the show’s thematic undercurrents — fear, truth, responsibility, connection — reflects a nuanced understanding of Sondheim and Lapine’s intentions.

Matt Kizer, Ted Zoldan, Eiko Moon-Yamamoto,
Olivia Hellman, Heather Orth, Maureen McVerry

When Into the Woods debuted in the late 1980s, many interpreted the mounting losses of Act II as a metaphor for the AIDS crisis. In 2025, it’s not hard to see echoes of a world wrestling with authoritarian pressures, eroding freedoms, and collective uncertainty. This production never strains for relevance, but it doesn’t resist resonance either. It lets the metaphor breathe.

The cast

Ultimately, Into the Woods offers the same wisdom it always has: that facing fears, telling difficult truths, and leaning on others is the closest any of us get to “happily ever after.” San Francisco Playhouse’s production honors that message with beauty, humor, and abundant heart.

Bay Area theatergoers of all ages should treat themselves to this trip Into the Woods.

The cast

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photos by Jessica Palopoli / San Francisco Playhouse

Into the Woods
San Francisco Playhouse, 450 Post Street in San Francisco
Tues-Thurs at 7; Wed at 2; Fri at 8; Sat at 3 & 8; Sun at 2
ends on January 17, 2026
for tickets ($52-$145), call 415.677.9596 or visit SF Playhouse

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