Stephen Sondheim’s Magic Transforms Curses to Choices  

by Francine Foltz  

People who like musicals with substance tend to be Stephen Sondheim fans, and for many,
the apotheosis of Sondheim’s writing is “Into the Woods,” which plays this holiday season at San Francisco Playhouse. Under the supremely able direction of Susi Damilano, a collection of fairy tales becomes a parable of transformation.

The story brings together the familiar figures of Little Red Riding Hood (perky Olivia Hellman), Cinderella (charming Jillian A. Smith), Jack of Beanstalk fame (brawny William I. Schmidt), and Jack’s long-suffering mother (melodious Eiko Moon-Yamamoto).

James Lapine’s inventive story unites them with The Baker (much-loved Phil Wong), his Wife (lovely Ruby Day), and the Witch (splendid Alison Ewing), whose curse they must try to remove. In the process, lessons are learned, and lives are lost.

Director Susi Damilano fills the stage with sensuous delights

Thanks to Heather Kenyon’s scenic design, the woods are “lovely, dark and deep.” Yet, somehow, the stage also accommodates three sub-sets and sixteen cavorting actors. Trevor March and Johann Santiago Santos play double roles: They first appear as lascivious wolves, enticing Red Riding Hood off the path in a dance both scary and exciting; then they appear as charming princes, intent on acquiring unattainable prizes.

Maureen McVerry plays Milky White, an appealing cow with Bo Peep leggings, and a mysterious narrator (Matt Kizer) poses meaningful riddles. A striking redhead in a gorgeous green gown (Alison Ewing) appears in a puff of smoke.

From her rotating tower, Rapunzel (Samantha Rich) sings a brief, beautiful aria. Jack retrieves riches from the land of giants. Cinderella reluctantly yields her slipper, while her greedy stepmother (Heather Orth) with her selfish daughters (Rachel Fobbs & Callahan Gillespie) get what they deserve.

Sondheim, soaring above it all

Sondheim’s score is performed by a band of hidden musicians. The songs range from duets to quintets to ensembles—all studded with stunning rhythms and comic rhymes. This is a fairy tale for grown-ups. Children will delight in the antics of the play: leaping princes and coloratura princesses. But after intermission, the happy ending implodes, and the residue of the characters’ thoughtless actions leaves a giant footprint.

The witch’s petulant complaint that “children don’t listen” transforms into the warning to ”be careful what you say: children WILL listen.” After many characters, including innocent ones, suffer for their past actions, we cling gratefully to the survivors’ claim that “we are not alone.”

“Into the Woods” tells a timely tale about human frailty. Finally, it’s the problematic love of parents for their children and the recognition of our mutual responsibilities that bind us to one another.

For all of us, young and old, Sondheim offers the antidote to Scrooge: “You are not alone! No one is alone!” Celebrate the true holiday message with this delightful, self-made family of survivors.

“Into the Woods” by Stephen Sondheim, book by James Lapine, directed by Susi Damilano, music direction by Dave Dobrusky, choreography by Nicole Helfer, scenic design by Heather Kenyon, at SF Playhouse, San Francisco. Info: sfplayhouse.org – to January 17, 2026.

Cast: Phil Wong, Ruby Day, Alison Ewing, Jillian A. Smith, Olivia Hellman, William I. Schmidt, Samantha Rich, Trevor March, Johann Santiago Santos, Heather Orth, Rachel Fobbs, Callahan Gillispie, Matt Kizer, Maureen McVerry, Eiko Moon-Yamamoto, and Ted Zoldan.