The best characters of Stephen Sondheim

1. Sweeney Todd - (Sweeney Todd: The Demon Barber of Fleet Street)

Does anyone fancy a pie? Mr Sweeney Todd is an intriguing mix of victim and villain, with a tragic past that saw him imprisoned for fifteen long years, Todd returns to England on a boat with nothing but vengeance on his mind. Where he much prefers terrorising his clientele to taking a trip to therapy. His blood-thirsting nature shows how retribution can destroy the soul, and it makes his character development extremely fascinating to witness.

Bludgeoning his customers with a razor and then dropping their corpses down to his partner in crime, Mrs Lovett (don’t worry, she made the list), Sweeney does it all with a haunting baritone, and Sonheim’s delicate compositions allow us a glimpse into the darkness of Todd’s mind and the intense emotions that drive his murderous actions.

2. The Baker’s Wife (Into the Woods)

She may run a small bakery nestled in the corner of a fairytale kingdom, but her life is far from a fairytale dream. Cursed with infertility by a witch and underestimated by her husband, The Baker’s Wife will stop at nothing to better her situation, even if it means (by The Wtiche’s orders) collecting ‘a cow as white as milk, the cape as red as blood, the hair as yellow as corn and the slipper as pure as gold’.

She is the better half of The Baker and is often the voice of reason within the story. Practical, wise and determined, The Baker’s Wife isn’t afraid to get the job done. 

3. Bobby (Company)

Bobby is many things, but he’s no quitter! A successful man in his mid-30s with a wife and two children, Bobby’s luxurious lifestyle comes at a hefty cost. Beneath the six-figure salary, substantial mortgage and Porsche payments, he fears becoming a failure, and when his steady job vanishes with the company downsizing amidst a financial crisis, Bobby must grapple with the loss of his house, his car, and his pride.

Bobby is fierce and quick-witted. His self-assured demeanour has shielded him from self-doubt in the past. However, this sense of security is now on the rocks, and he must come to terms with the possibility of a less extravagant lifestyle. He shows that no matter how wealthy you are, it’s how you feel on the inside that counts.

4. Mrs. Lovett (Sweeney Todd) 

One of Sondheim’s most tragic and gothic characters, Mrs. Lovett is driven by vindictive love. Born and raised in bleak 19th-century London, she is known for serving the ‘worst pies in London’, but fate has a funny way of figuring itself out.

She becomes involved in assisting Sweeney Todd. The bodies of his victims fall through a trap door, landing in Lovett's pie shop below, where she uses the remains as a secret ingredient. Her primary challenge lies in concealing the truth from Sweeney about his wife. She is determined to keep him for herself and protect her pie shop's newfound success. Despite showing an alarming lack of concern for killing people, she still possesses the odd flicker of compassion for orphans. 

5. Georges Seurat (Sunday in The Park With George) 

Georges shows that art can be an epic tool for self-discovery. He is a glimpse into the mind of a the real-life visionary painter of the same name known for his infamous painting "A Sunday Afternoon on the Island of La Grande Jatte,", and much like the real Georges Seurat, the fictional one is committed to his craft.

However, it’s the same dedication that consumes him, at points, there are times when Georges is shown to be completely absorbed in his work, so much so that it puts his personal relationships on the line, particularly with his mistress and model Dot. Others struggle to understand his emotional complexities and inner world, but as he wrestles with his creative process, he is able to see moments of clarity and introspection. 

Stephen Sondheim’s Old Friends tickets are available now!

Stephen Sondheim's Old Friends is making its way to the West End's Gielgud Theatre for a limited 16-week run from September 16, 2023, to January 6, 2024, after winning the 2023 WhatsOnStage Awards for Best Theatre Event. Celebrate the life and work of the legendary composer!