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Have I Got A Girl For You: Stephen Sondheim’s most fascinating female characters

Rosalie Craig plays Bobbie in the West End revival of 'Company': Dan Kennedy
Rosalie Craig plays Bobbie in the West End revival of 'Company': Dan Kennedy

No matter how many times you’ve seen Stephen Sondheim’s musical Company, you’ll find something new in the upcoming West End revival. Mainly because Bobby, the commitment-phobic leading man, is now Bobbie, played by Rosalie Craig. Director Marianne Elliot persuaded Sondheim to allow a gender change, explaining that doing so would allow her to explore the challenges women face today. “If you’re a woman in your thirties and you’ve got a really good job and you’ve got a great apartment and you’ve possibly got lots of boyfriends … all your friends will probably have an opinion,” said Elliot.

This is an exciting change for all theatregoers, Sondheim fans and otherwise – hopefully it will set a precedent for some more exciting roles for women on stages everywhere. However, Sondheim has never short-changed his actresses. He writes women who are complex; naive yet sophisticated; warm but bitter; who have lived lives filled with hope and despair. His girls get the best lines – and sometimes they even have the last laugh. Here are some of Sondheim’s unforgettable women.

Sally Durant Plummer (Follies)

When other female characters are restricted to being love interests, Sally makes love interesting. At 49, she’s still so close to her past self that she’s stalked onstage by her 19-year-old ghost, while clinging onto the increasingly untenable hope that her old boyfriend Ben (now her friend Phyllis’s husband) loves her as much as she loves him still. Sally’s beautiful and utterly devastating ballad “Losing My Mind” redefines unrequited love and yearning. Imelda Staunton played Sally in the recent revival at the National, giving real weight and depth to her pain and longing.

The Witch (Into the Woods)

A much misunderstood matriarch, Sondheim’s Witch evolves, arriving on stage as a villain and turning into a classic anti-heroine. The Witch controls the outcome of every fairy story, and shows herself to be capable of great cruelty and kindness – but when she hurts people, it’s an action borne out of a misguided attempt to protect them. Through the Witch, we understand the problems of being a bold, spiky three-dimensional woman in a world where we’re expected to be small, soft and quiet. It goes without saying that the Witch also has the biggest and best hair that has ever been seen on Broadway. Meryl Streep took on the role in the 2014 film – to play the Witch, as the meme has it, you’ve got to have the range.

Meryl Streep in the 2014 film adaption of ‘Into the Woods’ (Rex)
Meryl Streep in the 2014 film adaption of ‘Into the Woods’ (Rex)

Rose (Gypsy)

Before Kris Jenner, there was Rose, the ultimate fame-obsessed mother desperate to turn her two daughters into Vaudeville stars. Sondheim described his creation, drawn from the memoirs of Gypsy Rose Lee, as a “showbiz Oedipus”. This is a character who seems even more relevant in 2018 than she did in 1959 when the show made its Broadway debut. Rose’s pursuit of power and status tips from the ambitious to the delusional, but she shifts and dissembles almost seamlessly. Rose is both monstrous and achingly human; a woman who manages to be defined by motherhood while transcending it. If King Lear is the ultimate parent to play on stage, Rose must come a close second.

Desiree Armfeldt (A Little Night Music)

Some fans feel that Desiree is the archetypal Sondheim heroine – after all, she’s the one who sings his definitive song, “Send In The Clowns”. In fairness, Desiree is not Sondheim’s invention. A Little Night Music is an adaptation of Bergman’s comedy Smiles Of A Summer Night. Desiree is a glamorous actress with a diminishing reputation and fading career, who is reluctant to take care of her own child, and still in love with the child’s father Frederik, a former lover who has married an 18-year-old. In Sondheim’s skilful hands, Desiree’s story becomes triumphant. It’s the tale of a woman who is defined not by her beauty, but by her ability to hope and grow.

Mrs Lovett (Sweeney Todd)

Possibly one of Sondheim’s least nuanced characters, but perhaps the most fun, Mrs Lovett is the grande dame of gothic melodrama, and her appetite for guts, gore and revenge equals, and sometimes exceeds, that of the title character. Mrs Lovett is full of internal conflict, and often finds herself stuck in a hard place between love and loyalty. Pleasingly, she is much better at murdering than cooking, and inspires one of the greatest and most brutal acts of revenge in theatre history.

The cast of ‘Company’ in rehearsals (Helen Maybanks)
The cast of ‘Company’ in rehearsals (Helen Maybanks)

Phyllis Rogers Stone (Follies)

Phyllis is an icon for the Instagram generation – a glamorous, much-envied success story, with a life that’s falling apart beneath its glossy veneer. As the wife of her former best friend’s big love, Phyllis shows us that being the subject of someone else’s jealousy doesn’t always mean you have anything worth being jealous of. Her big song, “Could I Leave You”, is a magnificently waspish, blistering summary of a relationship at its end and the impossibility of maintaining a power balance.

Dot (Sunday in the Park With George)

Dot takes the unspoken title role here. As the lover and model of the artist Georges Seurat, she is the one who is committed to spending her Sundays in the park posing for him. The musical is inspired by the Seurat painting A Sunday Afternoon on the Island of the Grand Jatte, and Dot is one of the few female characters in a female musical to subvert the theory of the late art critic John Berger, who said that in art “men act and women appear”. Dot forces herself to act in order to be freed from George’s arresting gaze, although obviously she never stops loving him and struggling with her painful longing for him. If she did, it simply wouldn’t be Sondheim.

Joanne (Company)

A caustic serial divorcee, Joanne’s bitter, witty words serve as a cautionary tale to anyone who is overly fond of a self-deprecating joke. Joanne’s big song, “Ladies Who Lunch”, calls out the wealthy women who do nothing, Joanne being a woman who would rather humiliate herself publicly and passionately than stand on the sidelines watching. While Bobby, the central character, reduces Joanne to a series of characteristics he considers either desirable or unappealing, she is undeniably flawed and fascinating, and too big a personality to be reduced by his narrow labels. Elaine Stritch made the role famous, imbuing the character with a combination of earned confidence and flickering fragility. When we talk about dames, we’re talking about Stritch’s Joanne.

Company is at the Gielgud Theatre from 26 September to 22 December www.gielgudtheatre.co.uk