Interview: Emily Skinner Unpacks Desiree in A Little Night Music, La La La

The summer night may smile three times, but there does not appear to be a limit on the number of times A Little Night Music will smile on Emily Skinner. She pays her latest visit to the Stephen Sondheim-Hugh Wheeler musical at Barrington Stage Company alongside a dream cast that includes Jason Danieley, Sierra Boggess, and two-time Tony-nominated stage legend Mary Beth Peil. This time, however, Skinner will be taking her turn inside the "glamorous life" of one of Sondheim's most complex leading ladies, Desiree Armfeldt.

With a storied career — including a Tony nomination (which she shared with Alice Ripley in the original Broadway production of Side Show) and a laundry list of legendary bosses from Julie Andrews to Hal Prince — Skinner knows better than most what it's like to wend from stage to stage, building the beautiful yet complicated mosaic that is a life in the theater. Though she claims her natural temperament does not always match Desiree's, their life experiences share many parallels — and for a few weekends in the country, the two get to shake hands.

This interview has been condensed and edited for clarity.

I've heard this isn't your first A Little Night Music. How many times has this show circled back to you?
It's so bizarre. I've played Petra once and I've played Charlotte twice — and then I did a little bit of Desiree for Hal Prince in his retrospective show Prince of Broadway. So this is a show that keeps showing up in my world. I feel very lucky because it's such a beautiful gem of a show. It's the best of the best in my opinion.

Is it at the top of your Sondheim rankings?
I'm not that person who can say, "My favorite Sondheim show is this!" I just think they're all so magnificent and special and diverse. But I will say that I think the best writing is in the two Hugh Wheeler shows he did — Sweeney Todd and A Little Night Music. The scripts are so witty, they're so smart, and they're so meticulously well-crafted. It's just a gift for an actor to live in them because you really have to do very little. You just have to deliver it.

Do you find yourself connecting to new things in the show each time you come back to it and take on a new character?
Yeah! I'm always sort of amazed how wonderfully Sondheim writes for women. It's staggering to me. And this show is about so much. It's about love at all levels — romantic love, and parental love, and aging, and how you change as a person. It's interesting to play Desiree at this point in my life. She's an actress who's had a lovely life of adventure, and now she's sort of re-looking at her life and going, Does this still satiate me? Do I want this or do I want something else with someone? Do I want to change my life? I certainly relate to that at the point where I am post-pandemic.

Sondheim captures so much of that push and pull in "The Glamorous Life." How much does that song resonate with you as a performer?
I just love that it's about how not glamorous the glamorous life is [laughs]. It's a life of running around and working very hard, frenetically. It's such a genius, clever song. I think if you're a performer, there's some part of you that feels like this is what you're meant to do and it's what keeps you going back. I spent a lot of the pandemic sitting with myself and really not missing performing at all. So when I started performing again last year when things opened back up, it was an interesting experience to go, "Huh, I am enjoying this again." But I think I'm enjoying it in a different way. So it's interesting. I love it but I don't know that I feel a craving for it in a way that I maybe did in my 20s. When I was a younger actress, I used to see older actresses and think, "They have such a sense of ease about them." And I think that's part of it. You get to a certain point and there's an innate sense of comfort onstage.

Do you see that in Mary Beth Peil's performance as Madame Armfeldt?
I certainly do. Watching Mary Beth do this role is like watching a master work. She has this one song "Liaisons" and it's like watching a nine-act play. It's the most incredible thing I've ever seen. She mines that song in the most relaxed way. It's just incredible. To me, watching her is one of the highlights of this experience.

In all the Sondheim you've done, did you ever get to work with him personally?
I did. I worked with Sondheim a couple of times. He was always really lovely to me, and was always very meticulous. His ear was for the lyric. I remember I sang "Ladies Who Lunch" and he had one note for me. He said, "Very nice job. You sang 'a' instead of 'the'."

Any other memorable pieces of wisdom?
He was writing a piece with David Ives in the last couple years of his life and I was asked to do an early reading of just the first act of it at the Public. But I was about to go do Into the Woods at TUTS in Houston and I couldn't do it. I wrote him an email and said, "I'm so honored, but I can't participate because I'm actually going off to do another of your shows." He wrote back and was like, "What are you doing?" And I said, "I'm playing the Witch in Into the Woods." And he said, "Oh you'll be wonderful. You know she's bipolar." And I was —"REALLY? Tell me more!"

He wrote me this email talking about how the parts of the Witch that feel dangerous he wrote with the idea in mind that she swings emotionally on a dime, and he kept using the image of someone who was bipolar. Isn't that interesting? I'd never looked at it that way, but that was great insight. That knowledge definitely made me feel emboldened in playing that role.

What kind of emotional life are you giving your Desiree?
I've tried to play with a Desiree who's looking for the good. That sounds really saccharine when that comes out of my mouth. But even at the end of "Send in the Clowns," she spins it to a positive. I'm very moved by people who are like that because I don't know if I'm necessarily like that. And I think that's probably one of the reasons men like to be around her.

She's one of Sondheim's most iconic characters. Has she been on your personal bucket list?
I don't think I had a personal bucket list. It might have been on somebody else's bucket list for me [laughs]. I think my bucket list has always been just do a lot of Sondheim. And I figure if I just stick it out long enough, I'll get to do another Sondheim and another Sondheim…