One wouldn’t expect a Stephen Sondheim musical spun from fairy tales to be a Disney-esque affair. But “Into the Woods,” Sondheim and librettist James Lapine’s enduringly exquisite tip of the hat to the Brothers Grimm, owes just as great a debt to Sondheim’s mentor, the lyricist and librettist Oscar Hammerstein II, who channeled hope and wonder into songs and stories that could cut a lot deeper than those who thought him a cockeyed optimist ever grasped.  

Consider this deceptively simple lyric from the ballad “No One Is Alone,” as pure an example of Hammerstein’s influence as filtered through Sondheim’s distinctive genius as you can find: “Someone is on your side/Our side…Someone else is not/While we’re seeing our side /Maybe we forgot/They are not alone.”

You’d be hard pressed to find a more profound distillation of life, particularly life outside of one’s safety zone — precisely the part represented by the woods in Sondheim and Mr. Lapine’s 1986 musical, now being staged as part of New York City Center’s Encores series. The director is Lear de Bessonet, whose whimsical, insightful interpretations of Shakespeare and musical theater favorites alike have been duly praised in recent years.

It would seem an ideal match, and this concert staging eventually proves to be just that, albeit after something of a slow start. The starry cast includes the Tony Award-winning actress Heather Headley as the Witch, a role introduced by Bernadette Peters. Sara Bareilles, who was best known as a singer/songwriter before crafting the score for a musical adaptation of the film “Waitress,” is cast as the Baker’s Wife, who’s initially prevented from having a child by a curse the Witch placed on the Baker — played here by another Tony winner and musical theater favorite, Neil Patrick Harris.   

Ms. Bareilles, whose acting experience has been more limited than that of her co-stars, appears hesitant at first but then seems to bloom with the audience’s encouragement, singing potently and revealing a flair for dry comedy perfectly suited to her part. When she accidentally sang the wrong lyric during a recent performance, she improvised a correction with the flair of an expert trouper, earning approving laughter and applause.

Ms. Headley, surprisingly, seems a bit stiff herself during Act One, though this apparently stems less from anxiety than a choice to make the Witch more regal in her wickedness. Although elegance comes naturally to this actress, it’s only after her character undergoes a key transformation that Ms. Headley loosens up and really bites into this juicy role, relishing its humor and poignance.

Mr. Harris, making a welcome return to the New York stage, mines the same qualities in his less flamboyant character, while Denée Benton makes a lovely Cinderella — even if her performance won’t make anyone forget the sparkling vocals and wit that Laura Benanti brought to the 2002 Broadway revival, spoiling anyone who saw her forever. Tony winner Gavin Creel and rising star Jordan Donica sing beautifully and mug gamely as, respectively, Cinderella’s and Rapunzel’s Princes, with Mr. Creel also digging his teeth into the lascivious Wolf.

Yet some of the most winning performances in this “Into the Woods” are delivered by younger and less established players. Julia Lester is a deliciously droll Little Red Ridinghood, and Cole Thompson is brightly endearing as Jack, that famous beanstalk climber. As Rapunzel, Shereen Pimentel, whose glorious lyric soprano graced Broadway only briefly before her star turn in the most recent Broadway revival of “West Side Story” was cut short by the Covid shutdown, gets to bring it back in full force.

Ms. deBessonet has also recruited a chorus whose members range from public school students to local seniors for the rousing finale of “Into the Woods.” The amateur artists join the pros as they segue from yet another wise and ravishing ballad, “Children Will Listen,” into a reprise of the prologue that reflects the characters’ learned knowledge. It’s a canny way to conclude a journey that remains as universally relevant and moving as ever.