I was sitting the other night, catching up on this season of Orange is the New Black, and I was struck by just how terrific an actress Annie Golden is on the program. What makes her all-the-more special is the fact that her character doesn’t speak, but says so much with her eyes and her facial expressions. In one particularly thoughtful moment I found myself asking “Has she ever played Mrs. Lovett in Sweeney Todd?” I think this would be an inspired casting choice, and Golden is no stranger to Broadway musicals or playing psychotic Sondheim characters, having originated the role of Squeaky Fromme in the original Playwrights Horizon’s production of Assassins (1990).

This got me thinking: If I could cast some roles in Sondheim musicals, who would I choose and why? We all love a little speculative casting, so why not play that game right here. Today’s blog features some of my favorite choices for people I would cast in Sondheim roles.

A Little Night Music
Countess Charlotte Malcolm: Alison Fraser

Some might say that Alison Fraser has “aged-out” of this role, but I find her timeless onstage and will make the argument that can pull this off. The script for A Little Night Music is not specific about age, so I think we are fine here, especially since ability trumps years. Fraser has made a career out of playing quirky, offbeat characters, and the gloomy Charlotte Malcolm (with her acid tongue and morose demeanor) is the type of role in which Fraser can do in her sleep. I can already imagine the dryness with which she would deliver lines like “You are a tiger, I am a hawk. We are our own zoo.”

Merrily We Roll Along
Charley Kringas: Taran Killam
Mary Flynn: Ann Harada

As was witnessed by those who attended the Encores presentation of Little Shop of Horrors, "Saturday Night Live" regular, the hilarious Taran Killam, was born for the musical theatre. Killam specializes in a variety of roles, from over-the-top crazy to twitchingly neurotic. I think he would make a delightfully frantic Charley Kringas in Merrily We Roll Along, bringing his undaunted comedic chops to the tour-de-force number “Franklin Shepard, Inc.”. Sure, Charley is not all laughs, but everyone knows the best and most versatile comedic talents are latent dramatic performers. He’d be wonderful.

How about Ann Harada for Mary Flynn? Harada is best known for her broad humor in musicals such as Avenue Q, Les Miserables, and Cinderella, but even at its most outlandish, her delivery has always held an undercurrent of heart and warmth. In Merrily We Roll Along, Mary may be a drunk and she may be acerbic, but she is the glue that holds everyone together (well…until she no longer can). I think Harada would bring a sincerity to Mary that would be both winning and powerful.

Into the Woods
The Baker’s Wife: Laura Benanti

Ms. Benanti has already proven a luminescent Cinderella in Into the Woods, but I have always felt her timing and ability to turn a phrase were more-suited to the Baker’s Wife. The role is equal parts determination, frustration, humor, vulnerability, and earnestness. Benanti has proven, again and again, to be one of our most nuanced actresses, capable of navigating complex characters and infusing them with depth. I assert that a Benanti interpretation of “Moments in the Woods” would rival unforgettable turn originated Joanna Gleason.

Follies
Sally Durant Plummer: Betty Buckley

Betty Buckley just performed “I’m Still Here” in a concert version of Follies in London, and people raved. Truly, however, I think we would all be thrilled to see her in a leading role in Follies. Let’s envision her playing Sally Durant Plummer, wrapping her tremulous and gorgeous voice around songs like “In Buddy’s Eyes” and “Losing My Mind.” Buckley has always brought a bit of an edge and a quiet fragility to the characters she has portrayed onstage, and Sally would be the type of role she could really sink her teeth into.

Anyone Can Whistle
Cora Hoover Hooper: Joanna Gleason

For all the critics who hate the book to Anyone Can Whistle, I say “baaaah”. I find it to be sharp, intelligent, and biting satire. I think the character of Cora Hoover Hooper is a delicious character, full of contempt for those she leads, and making a mockery of the post for which she has been entrusted. “Me and My Town”, “The Miracle Song” and “A Parade in Town” are all terrific songs that shade this character with a variety of emotions and motivations. Why not marry this role with my favorite actress: Joanna Gleason. As she has proven, time and again, Gleason can find humor and heart in places others seem to overlook. She would flesh Cora out to be one of the most compelling characters to ever populate a Sondheim musical.

Sunday in the Park with George
George: Michael Cerveris

I will thank my sparring partner Robbie Rozelle for this suggestion, but for once, he and I wholeheartedly agree on something. Cerveris has proven a powerhouse performer of the American Musical stage, and he seems at home in a wide-range of challenging roles. His recent work in Fun Home, not to mention his reflective Sweeney Todd make him an ideal choice to inhabit the role of a detached artist who struggles to see his vision reach fruition. “Finishing the Hat” is just waiting for a performer like Cerveris to explore the crevices of its haunting, pointed meanings.

Sweeney Todd: The Demon Barber of Fleet Street

Sweeney Todd: Terrence Mann

Terrence Mann has made a career out of playing dark and misunderstood characters, from his icy, sinister control as Inspector Javert in the original Broadway production of Les Miserables, to the heartbreakingly, misguided Leon Czolgosz in Assassins. As dark, brooding, misunderstood characters go, Sweeney Todd is probably the most complex. Mann would be so much fun to watch in this role, and, I suspect, a little frightening.

Passion
Fosca: Open Call

I’m the one pers1on who doesn’t love this musical. Totally left cold by it, as a matter of fact. I was hypnotized by Donna Murphy’s performance in the original, and loved her despite how much I just didn’t care about any of the characters (We can have this debate in another article). I do, however, think Fosca is a challenging character to sing and act well, so I would want to see someone who could really do it justice on both accounts. I have wracked my brain, again and again and have not come up with the perfect fit. Perhaps my readers have an idea?

Company
Bobby: Jonathan Groff

Who wouldn’t want to see this? Jonathan Groff sings beautifully, he is easily one of the sexiest men on Broadway, he is charming, and he also registers a certain ambiguity onstage that makes him an interesting choice to play the non-committal Bobby in Company. Bobby also needs a cheeky sense of humor, which Groff has demonstrated, time and again, from his stunning impersonation of Sutton Foster’s performance in Anything Goes, to the way he delivered the wittier potions of Melchior Gabor’s sexual frustrations in Spring Awakening.

Assassins
John Wilkes Booth: John Cameron Mitchell

Fresh out of Hedwig’s high heels, I think it takes someone with three names to pull off a character with three names. All kidding aside, John Cameron Mitchell has a lovely voice and a theatricality that I think would perfectly capture the over-the-top John Wilkes Booth in Assassins. I can just hear him putting on that that southern accent, pouring forth his manifesto in “the Ballad of Booth.” Though he considers himself “retired from acting”, I think most of us would love to see more of him (Molina is Kiss of the Spider Woman, anyone?).

Now that you have read through, please contribute your thoughts on who YOU would like to see cast in various Sondheim roles.