Cast of Into the Woods (Photo by Billy Hardiman)
Theatre kids of a certain generation, myself included, were formed in the time of the great British mega-musical.
You know the ones, Cats, Les Mis, Phantom, Miss Saigon. But, tucked among them was one show with more heart than flash and funnier and smarter than an episode of Seinfeld.
Sondheim gets a bad rap, but at his best, and Into the Woods is him at his best, he is every bit as lyrical and masterful as his mentor, Oscar Hammerstein.
Why Stephen Sondheim Is a Genius and Into the Woods Is His Funniest Masterpiece
Stephen Sondheim isn’t just a composer and lyricist, he’s musical theatre’s Shakespeare. Revered for his wit, emotional complexity, and fearless innovation, Sondheim elevated the Broadway musical to an art form that could rival the best of literature or drama.
While choosing a single masterpiece from a career filled with genre-defining work (Sweeney Todd, Company, Sunday in the Park with George, to name a few) may seem impossible, one musical rises above the rest for its brilliance, accessibility,
emotional punch, and especially its comedy: Into the Woods.
Click image for video clip! Alyssa Chiarello* as The Witch, Nick Barakos* as Baker, and Meggie Siegrist* as Baker’s Wife. (Photo by Billy Hardiman)
Sondheim: The Architect of Intelligent Musical Theatre
Sondheim redefined what musicals could do. He wrote about real people – flawed, funny, sad, confused – and gave them songs that didn’t just entertain but revealed character and dilemma.
His lyrics were razor-sharp. He loved internal rhymes, wordplay, and rhythms that mirrored natural speech. He made the audience think and feel without ever dumbing anything down.
Where Rodgers and Hammerstein gave us soaring romance, Sondheim gave us moral ambiguity. Where others aimed for applause, Sondheim aimed for truth. And he did it with such elegance and precision that even the trickiest concepts felt effortless in his hands and to the audience.
Into the Woods: The Crown Jewel
Into the Woods (music and lyrics by Sondheim, book by James Lapine) premiered in 1987 and became an instant classic not just because of its ingenious concept (mashing up several beloved fairy tales), but because of how deeply it interrogates human desire, responsibility, and community.
But here’s the thing people often forget: Into the Woods is also hilarious.
While Sondheim’s other shows often dwell in melancholy or existential dread (Follies, Assassins), Into the Woods is bursting with comedy, especially in Act I. Its wit is baked into the characters, the structure, and the very idea of fairy tale characters being emotionally needy, neurotic, and self-aware.
Click image for video clip! Tre Moore as Jack. (Photo by Billy Hardiman)
The Lyrics Are Comedy Gold
Sondheim’s verbal dexterity is unmatched, and Into the Woods has some of his sharpest lyrics. Take Little Red Riding Hood’s line:
“Nice is different than good.”
It’s funny because it’s delivered with naive earnestness, and it also punches with philosophical weight.
Or one of the Prince’s self-aware confessions: “I was raised to be charming, not sincere.”
Every character talks too much, second-guesses themselves, and over-explains – like someone in a sitcom trying to rationalize terrible decisions. Their songs are comedic monologues that expose just how messy and ridiculous desire can be.
Click image for video clip! Liam Boyd* as Rapunzel’s Prince/Dance Captain and Shonn Wiley* as Cinderella’s Prince. (Photo by Billy Hardiman)
Self-Aware Fairy Tales
The show finds humor in turning classic tales inside out. Cinderella doesn’t quite want the prince, Rapunzel has a nervous breakdown, and the Princes—those paragons of heroic love—are mopey, narcissistic crybabies. “Agony,” their duet of manly suffering, is pure parody:
“Agony! Far more painful than yours!”
It’s a soap opera wrapped in a Disney spoof, played entirely straight, making it funnier.
Click image for video clip! Dani Apple* as Cinderella, Nick Barakos* as Baker, and Elyssa Blonder* as Little Red Ridinghood. (Photo by Billy Hardiman)
Sitcom-Style Structure
The first act of Into the Woods plays like a tightly written television sitcom. Characters cross paths, make wishes, mess everything up, and scramble to fix things before the curtain falls. Their desires—money, children, escape, love—collide increasingly absurdly, like a well-plotted episode of Frasier or Arrested Development.
And like any good sitcom, it balances humor with heart. We laugh at the characters, but we also root for them.
But Then Comes Act II…
Of course, part of what makes Into the Woods so remarkable is that the comedy gives way to something more profound. Act II asks: What happens after “happily ever after”? Actions have consequences. Wishes come with a cost. Parents die. Giants fall from the sky.
And even here, Sondheim still finds humor in grief, in absurdity, in the awkwardness of human behavior when everything falls apart. The laughs may become more bittersweet, but they never disappear entirely.
A Masterpiece of Balance
Into the Woods is the perfect showcase of Sondheim’s genius. It combines:
- His unmatched lyrical wit
- His love of complex structure
- His ability to blend comedy and tragedy
- His deep empathy for flawed humans
It’s not just his most accessible musical—it may be his funniest, at least in Act I. But it’s the emotional shift in Act II that transforms it from clever pastiche to lasting masterpiece.
We enter the woods laughing. We leave changed.
And that’s the magic of Sondheim.
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*Courtesy of Actors’ Equity Association, the union of professional actors and stage managers in the U.S
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