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'Into the Woods' an enchanting conclusion to Skylight's season

“No one is alone,” sing the characters of Into the Woods in the penultimate moments of the Steven Sondheim/James Lapine musical. It’s a fitting summation of the show’s themes.

For its final production of the season, Skylight Music Theatre has assembled a cast of mostly local actors and designers to guide the audience through one of musical theater’s most enchanting plays. They never let the cynical realism of this fractured fairy tale overwhelm the warmth and emotion at its core.

One of the few out-of-town transplants is director Edwin Cahill, from New York City, and the work he’s done here makes him a worthy addition to the Wisconsinites. 

Directing Into the Woods requires wrangling an eclectic cast of characters — Cinderella and her Prince (Natalie Ford and Joe Fransee), sweets-eating Little Red Riding Hood and beanstalk-climbing Jack (Kaylee Annable and Ryan Stajmiger), a witch (Susan Spencer), a narrator (Ray Jivoff), and a baker and his wife to round things off (an astounding duo: Jonathan Altman and Karen Estrada). It also requires many technical tricks: towers and giants and a cow so maligned for poor execution in other productions that it has its own website dedicated to the failures (Skylight will not be joining it). And on top of all that, you’re dealing with a Sondheim score, notoriously difficult for its chromatic challenges and dissonant moments.

Let’s take these one at a time. Into the Woods’ moral is about relying on your community, so it’s heartening to see the Skylight’s production does the same, with its cast members largely stronger in pairs or larger groups.

While the other fairy tales all get told through the course of Act I, the through-line of Into the Woods comes in the bakers’ quest to break a curse of childlessness placed on the family by the witch next door, who will reverse her spell if they bring her four strange items located in the woods.

So it’s fitting that Altman and Estrada too form the heart of the company, bearing much of the show’s comedy and pathos on their backs. The duo have wonderful comic timing, both with each other and separately — Altman’s ill-fated negotiations for various items are particularly good, as are Estrada’s pratfalls in her scenes with Cinderella and the Prince. And in the second act, that camaraderie ripens into marital tension that feels earned, with neither suggesting their love is non-existent even when the tragedies of the second act stretch them to the breaking point.

Among the rest of the leads, Spencer has a keen, keen grasp of her role as the Witch, relishing every appearance on stage, and Ford, Stajmiger and Annable are excellent additions to the party. They leave room for scene-stealers though. Fransee and his fellow Prince (Ian Toohill) get great mileage out of gallantly lunging about the woods, and Jivoff is a perfect choice to play the dual role of Narrator and Mysterious Man. The one role lets him be serious but eccentric, the other lets him dial the silliness up to eleven until the moment he truly needs to be serious.

They perform among one of the better sets Skylight has mounted this season, courtesy of Peter Dean Beck. The traditional three platforms that serve as the homes of the bakers, Cinderella and Jack have backdrops that look done in crayon by a child, and when they slide off, they reveal an ever-changing woods, with set pieces dropping from flyspace or moved on and off effortlessly by poles and ropes. 

The aforementioned Milky White is well-executed, with wheels and a handle so she can be carted about any which way. As are Shima Orans’ costumes, ranging from enchanting (a lush wolf costume complete with six-pack abs, and both of the Witch’s ensembles) to gloriously, brilliantly down-to-earth (the bakers, decked out in the garb you’d imagine a resident of Bay View or the East Side wearing on their way to Metro Market). 

Perhaps one of the few technical missteps is in the lack of any flourish for the witch as she departs — the woman can throw lightning; I’d like to see more than a blackout when she whirls offstage.

Musically, either the cast or the orchestra (or both) had enough trouble with their tempos that it was noticeable in multiple numbers, but they and conductor/music director Mark Mandarano straightened things out quickly. 

That meant you could get back to focusing on how otherwise wonderfully they tackled Sondheim’s score. The complex group numbers came off without a hitch, but once again, when the time came for solos, it was Estrada and Altman who rose to the top (although Spencer, whose first few moments as the Witch didn’t immediately impress me, warmed up considerably by her duet “Stay With Me” and won me over all together in the second act).

“Moments in the Woods” is always a show-stopping number for the Baker’s Wife (after a particular moment it’s best not to ruin for Woods newbies), but Estrada doesn’t quite play it that way. She comes to her particular realization slowly, with leaves still in her hair, and there’s a robust practicality in her voice that supports her wavering and then strengthened convictions.

And then “No More” — I mean, this song is sad, so it’s supposed to pull on your heartstrings, but it’s never been as moving to me as some of Sondheim’s other pieces. Altman changed that. With Jivoff at his side, he sings the song with a still-new grief, not afraid to let rage and selfishness be the emotions bubbling to the surface over heartbreak.

Life is more complicated than a fairy tale. That’s why, Into the Woods suggests, we have each other to help with it.

Into the Woods continues through June 14 at the Broadway Theatre Center. Performances are at 7:30 p.m. with 2 p.m. Sunday matinees. Tickets start at $23 and can be ordered at 414-291-7800 or skylightmusictheatre.org.

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