Stephen Sondheim’s 90th birthday is today. While tributes to his great musicals and greatest songs have been written, we are paying tribute to his greatest roles. The fifteen book musicals of his to reach Broadway have no fewer than 268 separate named characters – and lots more that are identified only by description such as the Baker in Into the Woods or the five admirals in Pacific Overtures.
We invited a few Sondheim fans to pick their three favorite characters. No one found it easy.
We start with the writer who protested the loudest.
Jeff Walker, theatre critic
Where to begin? Stephen Sondheim and his various collaborators have given the world some of the most complex characters in the annals of musical theatre. As a huge Sondheim fan, I am loathe to pick just one. The roll call is a veritable who is whom of musical characters: Sweeney Todd, and Mrs Lovett, Bobbie, Pseudolus, George and Dot, Fosca, Desiree, and the the whole cast of characters in Follies. Each one a rich blend of humanity and lyricism that give the actor much to play and the audience much to appreciate.
Here, I begrudgingly boil down the list to my top three.
#3 Benjamin Stone, Follies
#2 Dot, Sunday in the Park with George
#1 Mrs. Lovett, Sweeney Todd
I am drawn to the canny, entrepreneurial spirit and ultimately entertaining Mrs. Nellie Lovett of Fleet Street, London. Sure, the show is called “Sweeney Todd The Demon Barber of Fleet Street,” but without Mrs. Lovett, Sweeney would have been just an angry man with an eager set of razors. Mrs. Lovett’s years long crush on the man formerly known as Benjamin Barker kept a light of hope and romance alive in her heart. It also blinded her to his real nature, and her own, if the truth be known. Nellie gave Sweeney a higher purpose, a focus to his work, and turned his vengeance into a lucrative enterprise where they could help their fellow man devour each other while putting money in their pockets. Plus, Mrs. Lovett does all of this with a musical hall entertainer’s flair, especially as performed by the original Nellie, the incomparable Angela Lansbury. The Tony Award-winner won her fourth leading actress in a musical award during the 1979-80 season for her indelible portrayal of Mrs. Lovett; her costar, Len Cariou also took home a Tony, as did Sondheim for his score and Hugh Wheeler for the book of the production.
Luckily for all of us, Lansbury’s performance as Mrs. Lovett was recorded during its national tour with Sweeney replacement George Hearn. I have seen a number of Lovett’s in my day, but, to me, none comes close to Angela Lansbury. Those eyes, the vivid expression, her glances at Sweeney, her timing – each gesture and delivery perfectly timed to seduce the audience into a potent spell with show biz panache.
Our next three guests agree about Sweeney Todd.
Brad Hathaway, theatre critic
#3 Charles Guiteau, Assassins
#2 The Baker’s Wife, Into The Woods
#1 Sweeney Todd, Sweeney Todd
Sweeney Todd. Sondheim’s accomplishment in creating the musical Sweeney Todd is monumental and its supreme element is its title character who is shown at many steps in his transition from man to monster. The amazing thing is that he is, if not a sympathetic character to the end, certainly an understandable one whose motivations are clear and human. He begins the evening as a wronged man seeking to recoup what he has lost – his wife and daughter from whom he was unconscionably separated. He ends up as a depraved serial killer. While that transition happens in measured doses, it is in the song “Epiphany” that he snaps completely.
Teddie Hathaway, artist
#1 Mrs. Lovett, Sweeney Todd
Without a doubt I think Sondheim’s greatest character is Mrs. Lovett. I suppose it’s natural to have a particular fondness for a character because of who you have seen in her skin. I’ve been fortunate to see Sweeney Todd numerous times populated by many of the greats. But once you have seen Angela Lansbury play her, there is no one else.
Angela’s Mrs. Lovett is multifaceted – melancholy, calculating, coy and ghoulish – though I supposed Mr. Sondheim had something to do with that too. She was honestly attached to Toby, but was willing to kill him to keep him quiet. She was caring (or calculating) enough that although she saved Sweeney’s razors for years because they were valuable, she gave them back to him when he showed up, just to lure him in. But her idea to use Sweeney’s victims for her pies – “Have a little Priest” – defined her. Thanks to Angela (and Mr. Sondheim) Mrs. Lovett was believably despicable, kind, macabre and funny all at the same time.
Jimmy Mavrikes, performer and Co-Artistic Director of Monumental Theatre
#3 Jack, Into the Woods
#2 Dot, Sunday in the Park with George
#1 Mrs. Lovett, Sweeney Todd
Why? Because how ridiculous is it that she can’t make a good meat pie till she uses human flesh? I just love-it.

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Jayne Blanchard, theatre critic
#3 Mary Flynn, Merrily We Roll Along
#2 Dot, Sunday in the Park with George
#1 Fosca, Passion
When was the last time a leading lady in a musical was homely on purpose? And ugly, in the sense that obsessive love, illness, sheer will and determination distorted and scarred this woman, body and soul. I’ll give you a minute.
It was Stephen Sondheim’s daring genius in his masterwork Passion that gave us Fosca, a woman who reveled in her ability to repel and disgust. She is a woman seen not in the male gaze, but as a force of nature as awful to look upon as a harpy. But how she sings, how she loves the young soldier, manipulating him and taunting him until he’s convinced her kind of love–twisted, tortured–is the only true kind. When I saw Donna Murphy in the original Broadway production, I was so entranced and skeeved out, I sat there and cried with a total stranger, my seatmate, after the curtain came down.
Steven McKnight, theatre critic
#3 Sweeney Todd, Sweeney Todd
#2 George, Sunday in the Park with George
#1 The Baker’s Wife, Into the Woods
Sondheim’s greatest character, a woman without a name who doesn’t even survive until the final curtain? A definitive YES because the Baker’s Wife is the heart of one of Sondheim’s most accessible and beloved musicals.While the other characters are largely just fairy tale characters, the Baker’s Wife is the one character with a modern sensibility that vibes with the audience. Her ultimate song Moments in the Woods is classic Sondheim, witty and playful on the surface while addressing life’s deep ethical challenges. It’s a stand-out role that won Joanna Gleason a well-deserved Best Actress Tony Award.

Toby Orenstein, Artistic Director, Toby’s Dinner Theatre
#2 Mrs Lovett, Sweeney Todd
#1. (a tie) George and Dot, Sunday in the Park with George
I could not pick my favorite between George and Dot as they both share a huge spot in my heart.
The year is 1990 and I have just obtained the rights to my favorite musical Sunday in the Park with George. I was obsessed with the piece and I cast an actress who was just moving to the area, Sherri Edelen, to play Dot and Ryan Perry as George. George is the male version of me. He is obsessed with his painting. As obsessed as I was with directing this show. The beautiful song “Move On” is an anthem not to miss out on life that is happening around us. The obsessiveness of George for perfection and the understanding of Dot but realizing that life must go on were life lessons for me as a director, wife and mother. I have a room in my home dedicated to this show and I thank Stephen Sondheim for giving us the gift of this most beautiful musical.
Absent a recording from Toby’s production, here is Bernadette Peters and Mandy Patinkin performing “Move On”.
Susan Galbraith, theatre critic and Artistic Director of Alliance for New Music-Theatre
#3 Mother, Pacific Overtures
#2 Fosca, Passion
#1 Joanne, Company
When Sondheim wrote “The Ladies Who Lunch” for Company, he handed Elaine Stritch her first signature song, one audiences would demand for the rest of her career. Even on opening night in 1970, she delivered those zingers like no one else. She could “kill” with a look and get away with it because she was so screamingly funny. The song redefined for me what musical singing could be – raw and powerful.
Here, she records Company‘s Broadway album.
Jonathan Mandell, theatre critic
I can’t say that Stephen Sondheim is especially known for focusing on character development; that’s not what makes him great. What makes his characters memorable are the songs they’re given to sing.
#4 Emma Goldman, Assassins
#3 (tie) Desiree and Madame Armfeldt, A Little Night Music
#2 Amy, Company
#1 Carlotta Campion, Follies
I pick Carlotta Campion, the former showgirl from Follies, because of the song “I’m Still Here,” which has particular resonance at the moment. Originated by Yvonne De Carlo in the original 1971 Broadway productions, it’s one of Sondheim’s songs that’s taken on a life of its own, with everybody from Eartha Kitt to Barbra Streisand to Shirley MacLaine to Broadway actress and cabaret singer Sally Mayes to Chris Colfer in Glee. But, for the all time greatest performance, I’ll pick Elaine Stritch, who once said nobody should sing that song before the age of 80.
HAPPY BIRTHDAY, MR SONDHEIM.
Playbill has just posted birthday wishes and songs from Broadway stars. Watch it here.
Now it’s your turn.
Who are your Sondheim characters? What Sondheim memories do you have?