Tony Award Winner Joanna Gleason Explores Life’s Shouldn’ts and Shoulds at 54 Below

Chatting with the star of Broadway’s ”Into the Woods” and ”Dirty Rotten Scoundrels” as she prepares to make her cabaret debut.

It’s hard to believe that Joanna Gleason, a Tony Award winner for her definitive performance as The Baker’s Wife in Stephen Sondheim and James Lapine’s Into the Woods, has never done a cabaret show. Well, until now. Gleason, who has also been seen on stage in Dirty Rotten Scoundrels and Sons of the Prophet (among many others), makes her cabaret debut at 54 Below on October 9, 16, and 23 with a concert that explores her life’s important, defining moments. The actress fills us in on those moments, and her thoughts on the upcoming Into the Woods film, in the interview below.

Joanna Gleason
Joanna Gleason
(© Michael Crook)

Really, how is this your first cabaret show?
Joanna Gleason: I want to say that I’ve dodged it. I’ve been asked “Do you have a show?” for twenty-five years and I’ve always said “No, no, no.” I’m not one of those glorious song birds, the women and men who do these kinds of evenings. Truly, it’s not what I do…In Provincetown this last summer, it came about that I did two nights at the Art House. The first half was a play by Michael Patrick King, a very funny, twenty-five-minute one-person thing. Then, Seth Rudetsky interviewed me and I had the guys from Well-Strung. Do you know Well-Strung?

I don’t.

Joanna Gleason: It’s a gay string quartet. These men are heaven and they played that show for me and I sang four songs. Then, [54 Below Director of Original Programming] Phil Bond called me and said, “Would you like to do three nights in October?” This was the fight-or-flight moment. I’ve taken on so many things these last few years that I never thought I could do or secretly dreamed of doing. I said yes and I wrote a show. I have Well-Strung with me. As I’ve been writing it, I revealed to myself that there is, in fact, a window in to me that would maybe make it a kind of interesting, hopefully funny, night.

It’s an autobiographical show?

Joanna Gleason: It’s completely autobiographical, but it’s also what was in my head and some of the more pressing exigencies around my life that were not really well-known. How you get to be where you are right now not professionally, but personally.

So where are you right now?

Joanna Gleason: The simplest answer is I’m living on a tiny farm with Chris Sarandon. We’ve lived together for twenty-two years. I wrote a screenplay and it’s gaining traction and it’s being cast right now. I’ve written a novel. I’ve studied tango and I compete in ballroom competitions. I have one on Friday as a matter of fact. It’s about quality of life right now. And also, the bigger thing with doing this show is that I was at a point in my career where I wanted to tell the stories I wanted to tell. It’s so rare that you get cast in something where — it’s hard to find the great roles.

That’s unfortunate.
Joanna Gleason: The last great one was Sons of the Prophet. What a play. That was definitely a character [whom] I adored; a whole play that I adored. It’s very hard. You age out of anything interesting and good. That’s where I found myself. So I thought, why don’t I tell my own stories? So I started writing. I thought, I want to dance. If we can’t have fun now, after all the work, then when?

Have you seen any shows at 54 Below?
Joanna Gleason: I saw my sweetheart [and Dirty Rotten Scoundrels costar] Sherie Rene Scott do her show there, and Adam Guettel’s show. Part of me is terrified; do you know what I mean? Or, in the words of Sondheim, excited AND scared. It’s both things, but I’m just going to put it out there.

Tell me about your song choices.
Joanna Gleason: They’re mostly pop. There is, of course, some Sondheim in there. Of course.

How could there not be?
Joanna Gleason: I say in it, “Villagers with pitchforks would chase me to the river if I didn’t.” I’m going to have an able assist on that one. I don’t know if I want to say who…

I can imagine…
Joanna Gleason: [That person] and I sing…There’s a funny version of a completely different song. Then I go into “Moments in the Woods.” I’m also going to be singing from Nick and Nora. There are some old standards; a couple of things from the forties that I sing because it’s part of a section of a dream world that I lived in when I was a little girl. There’s a Johnny Mathis song, a twist on a Peggy Lee song, Billy Joel, James Taylor…and something from the Dixie Chicks. We don’t sing show tunes around the house, we never have. It’s the music that means something to me, the underscoring for the story I’m telling. It’s all about context. It’s about what these songs mean at a time in my life that maybe had nothing to do with [the time in my life that I sang them].

In what way did “Moments in the Woods” factor into your life when you were singing it eight times a week?
Joanna Gleason: I was in a completely “and/or” situation. I talk about it largely in the show. My life was quite divided for many years. Pieces of it were scattered all over the place. It’s about the thing of being able to have it all.

Will Into the Woods work as a film, in your opinion?
Joanna Gleason: It’s in very good hands. It has a pretty spectacular cast. I think that Emily Blunt is a beautiful choice for The Baker’s Wife. I’m a huge fan of hers. Am I proprietary or possessive of that show? A little bit; sure. We all are.

Is Broadway your be-all/end-all anymore?
Joanna Gleason: No, it’s not, actually. It’s monumentally time- and energy-consuming. It would have to be the kind of role that I wake up thinking about it and going to sleep thinking about it. I have to do this role. Of course I would. With the possibility of directing the movie that I wrote, the possibility of a novel getting published, and with this crazy other thing about performing in different ways — tango, cabaret — I find that my plate is really quite full. That’s not to say that if someone comes along and says, “Take a look at this…” and I think to myself “Okay…” I will commute six days a week. I will do it again.