The best characters of Stephen Sondheim
Standing ovations, critical acclaim, and a legacy that redefined Broadway and the West End – Stephen Sondheim’s musicals have it all. Known for his razor-sharp wit, emotional complexity, and masterful storytelling, Sondheim created characters that range from tragic antiheroes to whimsical dreamers. Each role is unforgettable, brought to life with lyrics and melodies that cut straight to the heart. And with Into the Woods returning to London at the Bridge Theatre from 2 December 2025, directed by Jordan Fein, there’s no better time to celebrate the best Stephen Sondheim characters of all time.
1. Sweeney Todd (Sweeney Todd: The Demon Barber of Fleet Street)
Dark, dangerous, and disturbingly sympathetic, Sweeney Todd remains one of Sondheim’s greatest creations. Wrongfully imprisoned for fifteen years, Todd returns to London hungry for vengeance. Armed with his razor, he unleashes terror on unsuspecting customers while partnering with Mrs. Lovett, the pie shop owner who finds a grisly way to make use of the bodies.
Todd is both victim and villain, a tragic antihero whose haunting baritone and tortured psyche make him endlessly fascinating. Through songs like “Epiphany” and “My Friends,” Sondheim plunges us into the depths of his madness, crafting one of musical theatre’s most chilling characters.
2. The Baker’s Wife (Into the Woods)
Smart, practical, and full of quiet determination, The Baker’s Wife is the beating heart of Into the Woods. She may run a small bakery, but her dreams are far bigger. Cursed with infertility by the Witch, she embarks on a fantastical quest to break the spell, tracking down a cow as white as milk, a cape as red as blood, hair as yellow as corn, and a slipper as pure as gold.
Unlike her husband, she’s resourceful and quick to act, often serving as the voice of reason. The Baker’s Wife represents desire, compromise, and the bittersweet reality that happy endings are rarely simple. Her character arc, especially in “Moments in the Woods,” captures the complexity of love, longing, and sacrifice in a way only Sondheim could write.
3. Bobby (Company)
Bobby (or Bobbie, in the acclaimed gender-swapped revival) is one of musical theatre’s most complex protagonists. Turning 35, unmarried, and surrounded by married friends, Bobby is forced to reflect on his life, his choices, and his fear of intimacy. Through iconic numbers like “Being Alive” and “Someone Is Waiting”, Sondheim explores the messy, modern realities of love, loneliness, and commitment.
Far from a traditional romantic lead, Bobby is flawed, conflicted, and achingly human. It’s this honesty that makes him one of Sondheim’s most relatable characters - proof that sometimes the scariest journey isn’t into the woods, but into your own heart.
4. Desiree Armfeldt (A Little Night Music)
World-weary yet enchanting, Desiree Armfeldt is one of Sondheim’s most glamorous creations. A celebrated actress juggling lovers, regrets, and rekindled passion, Desiree embodies the sophisticated wit of A Little Night Music.
Her show-stopping ballad, “Send in the Clowns”, has become one of Sondheim’s most famous songs – a moment of vulnerability where Desiree’s mask slips to reveal heartbreak and longing. Complex, witty, and deeply human, she’s a reminder that love is rarely simple, but always worth pursuing.
5. Georges Seurat (Sunday in the Park with George)
Inspired by the real-life French painter, Sondheim’s Georges Seurat is an obsessive artist consumed by his vision. In Sunday in the Park with George, his dedication to craft pushes away the people he loves – especially Dot, his muse and mistress.
Through songs like “Finishing the Hat,” Sondheim gives voice to the tension between art and life, showing the sacrifices of genius and the loneliness of creation. Georges isn’t warm or charming, but he is endlessly compelling, a character who speaks to anyone who has struggled to balance passion with connection.
Why Sondheim’s characters endure
From the murderous wit of Sweeney Todd to the bittersweet dreams of The Baker’s Wife and the aching vulnerability of Bobby and Desiree, Stephen Sondheim’s characters are as iconic as the musicals themselves. They’re messy, layered, and deeply human – and that’s why we love them. As Into the Woods prepares to take over The Bridge Theatre in December 2025, it’s clear that Sondheim’s legacy will keep enchanting audiences for generations to come.