For years, Amy Jo Jackson has been bringing commanding female characters to life, like Madame Blood in Kapow-i GoGo, Magenta in The Rocky Horror Picture Show, and Ursula in The Little Mermaid. In her newest 54 Below show, however, she is owning her feminine power by singing songs traditionally performed by men. I am thrilled to share my interview with Amy, where we talked about her show I Want To Be Your Man as well as cross-gender casting and the macho men she is dying to play on-stage.

The last time that I interviewed you was for Kapow-i GoGo, where you played Madame Blood.

Indeed it was!

What have you been up to since then?

I’ve been quite busy since then. Over the holidays, I played Ursula in The Little Mermaid down in Little Rock at Arkansas Repertory Theatre, which was amazing. It was an amazing cast. Sold out every performance before tech was over, so then we added a few shows. Kids in costume at every single performance…

Aww, that’s adorable!

Adorable! I made a child vomit out of fear. I’ll never do better. Never, ever do better. I found out like two hours after the show from the choreographer. So that was pretty sensational, and then I went to Cape Cod to the Wellfleet Harbor Actors Theater to do A Midsummer Night’s Dream. I played Titania and Hippolyta, so I just got back from that at the beginning of April. I’ve been playing lots of queen characters, which is lovely, and now I’m working on this show.

How long have you been working on it at this point?

It’s an idea I had – I usually have about five ideas in the hopper, like at some point I want to put together a show about this, or not even about this but with this kind of feel to it. I can’t remember why I decided May, but I was like, you know, I want to do another show. I’m feeling antsy. I’m feeling like I want to do another piece, and I think it’s just the one that seemed the most appropriate right now. It is stuff that a lot of friends of mine and I have been talking about with regards to women in theater and on stage.

Could you talk a little bit about what the show is and where the title I Want To Be Your Man comes from?

Certainly! The show is me, singing all-male material. It’s not a gender-reverse cabaret, and I’m not having men come on to sing women’s songs. It’s all material for men. I have guests coming on, but they’re all women. We’re all going to sing male material, partially because I’m six feet tall. I’ve played a lot of men in my time. The fact that I just did Shakespeare and played two women is unusual. I’ve played a lot of men in Shakespeare, so I usually do at least one gender-bent number in the show, and I thought that would be a really interesting thing to explore.

I remember going to this group where people get up and do speeches, which primarily focused on Shakespeare, but you can do whatever you want. I was going to get up one night, and I didn’t make the list in time, so I was out with a bunch of people afterwards that I didn’t know that well. And they were like, “What would you have done?” And I said, “Oh, I would do this speech from King Lear. I would do Edmund.” And all these guys – I realize at this point that I’m sitting at a table full of men – they’re all like, “Why would you do Edmund? I mean, that’s so interesting.” I was like, “I think it’s very interesting to do men’s speeches. I enjoy playing with androgyny,” and they’re all like, “You think you look androgynous?” And I said, “There’s an inherent androgyny to a women playing a male role.”

There is something about the athleticism and the way these men are written, the directness and the confidence that is very satisfying to do. Of course, there are women who are written to be strong and confident, but there are a lot fewer of them than there are just like, “I’m just a regular Joe off the street, but I still have a very firm opinion and no problem asserting it.” And there is something that is very impacting about getting to live in that space and getting to be a woman singing some of these songs.

Some are songs that are not necessarily about being masculine, but they have a particular point of view that I think is inherently male in one way or another. I’m exploring a bunch of different perspectives.

I was curious, did you hear that Shakespeare in the Park is doing an all-female production of Taming of the Shrew?

Starring Janet McTeer, goddess of my universe? Yeah. (laughs) I think I cried when I found out because I also love Cush Jumbo. I think they’re both wonderful. I’ve actually been up for Petruchio before, and yeah, I’m so excited about it. I have a couple of friends in it, and I cannot wait. I think it’s going to be very kick-ass, especially a play like that, which is about, in a lot of ways, gender politics.

Yeah, and it’s really tricky to do nowadays.

It is!

The sexism in that show is insane!

You do have to have a clear vision of how you’re going to look at it. People try to massage it in a way, and it’s like, this is the play! It’s not pretty. You have to find a way to reconcile it to whatever point you are trying to make, but the ways I have seen it most successfully done and explored in a way that feels full are single-gender. I saw an amazing all-male production. I’m excited to see this one, but that’s when I’ve seen it ferociously itself, able to explore without us all going, “Ehhhh…” in the same way.

Could you talk about the other women who are going to be in the show with you?

Sure! I have one song which is a quartet, so I’m going to have several friends from different parts of my life on to sing that with me. Audra Cramer, who was my understudy in The Little Mermaid, and Deborah Berenson who I met at 54 Below doing this concert lab that I hosted there last summer. She is wonderful, and I have Sarah White, who I met at the Flea working on The Mysteries, so that’s going to be very exciting. And then I’m singing a duet with Lilli Cooper who is a fantastic, ferocious force of nature and has a voice like you would not believe. She’s doing SpongeBob right now. She’s rehearsing for that, but lucky for me, they are rehearsing in New York.

How many of these shows have you done before, like cabaret-style shows?

Solo shows, this will be my third engagement at 54 Below, but it will be my second completely-different show. My first one was September 5, 2014, and then last year, I did essentially the same show, same skeleton. I would say two-thirds of the show was the same, and then we modified certain pieces. I’ve performed there a lot. I’ve hosted some evenings, but this is my second complete show that I’ve put together.

How do you choose the music that you’re going to use in it, and are there any composers that you really enjoy?

I start with playlists. That’s how I actually get ideas. I feel like all of this goes together, so I’m going to put it in a playlist. My first show was just songs I had put onto every playlist for years. I feel like this song belongs in the show if it is on my mind that much, but I’m also listening for a through line and moving them around on a playlist going, okay, maybe this is saying too much of the same thing as this. But that’s how I start because I’m so aural. I’m also a voice and speech person and a dialect coach, so I’m really responsive to how things inform what is performed before and after.

I started with musicals, even though I’m doing a lot of rock and pop in the show as well, but I started with musicals because that’s obviously what I think of when I’m like, what characters would I want to play that it would be much difficult to be cast as. I also thought, what are the most stereotypical male masculine characters I can think of? And then I put all of those songs into this playlist. It was like 100 songs long, and I started asking what I was really interested in singing and asking what is fun too, because it’s not a heavy show. I think it’s going to be very funny and has an upbeat kind of celebratory feel.

As far as composers, there are so many! So many good ones. I was really glad that I got a Rodgers and Hammerstein song into this show. I love Sondheim. That’s an obvious answer. I’m working with a lot of different composers this time around because I am doing some rock and punk, so I’m not working with traditional theater composers the same way that I’ve been before. In general, I love Michael John LaChiusa and Adam Guettel, and I do a lot of their stuff just in general. I’ve worked a Guettel into the show. I’m very excited about that. Stuff that is really tricky to do in an audition because it is musically complicated for a pianist is stuff that is very exciting to do in a cabaret.

I read recently that with Hamilton, Lin-Manuel Miranda is open to casting women in the male roles in the show. What are your feelings on this, and do you think more shows will adopt this because Hamilton is so big and everyone is trying to figure out that special formula?

I hope so. We’ve been making such headway in non-traditional casting in regards to race, which is super exciting and I think necessary. People need to see themselves reflected in a positive way, which is why it is so important to have an inclusive experience, and I do feel like that’s very true of women. I just got engaged, which is very exciting.

Yes, congratulations!

Thank you! But I immediately found myself very overwhelmed by people asking me questions that I was like, well, that feels private to me or that is none of your business. But this idea of, haven’t you been thinking about this your whole life because you’re female? Well, no. I think the rom-com grip, the grip that the rom-com has on our expectations of what women are supposed to be.

With the show I was just in, there were a bunch of us living at the actor’s housing, and The Bachelor finale was on. They were all watching it, and I was kind of trying to do my work in the corner and half watching it. Eventually, I just started watching, and I was like, this is shocking. I’m not opposed to reality shows. RuPaul’s Drag Race is my favorite show, but something about it really upset me. This is what we’re supposed to be supporting and applauding and wanting? You have these two women who are like, “Oh gosh, I sure hope he proposes to me!” Something about it just turned my stomach.

I think having women play either roles that were originally conceived to be played by men that then they just happen to make female – take the Sigourney Weaver track, do that, that sounds great – or roles that are supposed to be male but just putting a woman and not having it necessarily be a big statement. This is done with men quite frequently, where a man will play a role that is traditionally female, like Bracknell in The Importance of Being Earnest is coming to mind, but we don’t see that done as much with women.

I was always the type – I don’t know if this is a type, but this is me. I grew up watching Annie and wanting to be Miss Hannigan. I would sing “Little Girls” sitting on the edge of the tub with my hair in my sponge rollers with a glass of water because I didn’t know what gin was.

This was me in my childhood, so of course I want to be Matilda when I got a little bit older, but then I’m like, no, I want to be Trunchbull! And then she comes out, and it’s a man, and I get why, but it’s like, ah, curses!

Ursula is often played by a drag queen, which again is fierce but sad. It’s a very male-heavy show, so I think if it’s a way to level the playing field and create more opportunities for really meaty, exciting roles for more women, that’s really exciting for young girls to be able to see that and think, “Oh, that’s a thing I could do!”

I played Sir Toby Belch in an all-female production of Twelfth Night. We did performances at parks all around the city, and we did the show four nights in a row at Sunset Park. This little girl came to every single show, and on the last show, she had made these little pendants, like a little banner, and it said, “Girls Doing Shakespeare!” She drew on it, and we were all disasters. (laughs) This is the most amazing thing!

With Waitress opening this season, it will be the first time a Broadway show has had an entirely female creative team, and it’s really exciting because again, girls can see it and know that there is a place for them in directing or writing.

Another one was Fun Home. I was talking to a friend, and he said, “I didn’t really care for Fun Home. I thought it was kind of boring.” I was like, okay, part of that could be personal taste, but part of it is you’re bored because you aren’t seeing yourself reflected in any way. Imagine how we must feel all the time. We’re disengaged. Not bored, but not willing to investigate a world that is not the one that I inhabit. I think it’s very important for people to see these incredibly deep and beautiful songs and relationships and not being portrayed as frothy or having no agency.

I’m singing in this event at Joe’s Pub next week that this friend of mine has this blog called Cast Them Loose where she takes really egregious character breakdowns. Sometimes the breakdown itself isn’t the problem, it’s the problem that you use “yet.” Smart yet attractive. If you changed one word, this breakdown wouldn’t have an issue. So she’s doing this show at Joe’s Pub, and it’s definitely a lot of prostitutes. So many strong yet innocent or strong, capable personality while still being attractive.

I read that you are going to be donating half of the proceeds from the show to She’s The First. Could you talk a little bit about the organization and why it was important for you to support it?

Sure. They are this amazing, fairly small organization. They sponsor scholars in low-income countries so that these girls can be the first in their family to graduate high school. I’m getting emotional just talking about it. It’s so beautiful. I think someone was posting about the organization on Facebook, and at the time, I was looking for an organization to make a donation to as a wedding present. And then I went to Ethiopia two years ago and worked in a little village for just a week, but as you expect, it was extremely eye-opening.

The organization works with girls in African countries and in India and a number of other countries, and they have such an upward message of supporting a traditionally left behind group. When women can get out there and learn and get jobs, it just makes life better for everyone.

We are donating half of the ticket sales to this organization, which will go towards sponsoring a specific scholar, so I’ll be able to share updates on her. I think it’s exciting that people can have even a tangential impact by buying a ticket to a show, knowing that in some small way, they are affecting someone’s life.

You mentioned about male roles that you really enjoy. If what we were discussing earlier came to fruition and more shows started doing cross-gender casting, what are the five roles that you would want to play and why?

I’m going to limit myself to one Shakespeare because we accept that a lot more readily, but if I do one Shakespeare, and there are so many I want to do, Richard II. Let’s say that. It would be so interesting, and Fiona Shaw has already done it, so there is a precedent. I would love to play Gaston in Beauty and the Beast. I think he is hilarious. I would love to play Jamie Tyrone in Long Day’s Journey Into Night. I want to play Sweeney Todd, but I also want to play Mrs. Lovett. Henry Higgins! I would love to play Henry Higgins. I’ve sung “I’ve Grown Accustomed To Her Face” in shows a couple of times, and there’s something so delicious about hearing a woman spout all this chauvinistic stuff. Maybe Harold Hill? I seem to be really drawn to jerks! (laughs) But I’ve played a lot of villains.

I was actually just talking about The Music Man this morning with a friend, and Harold Hill, it’s a really hard role to pull off really well because you have to be so charming.

Anti-heroes are difficult. My dad hates The Music Man specifically because this guy is a liar, and the whole town gets behind him like, oh, you’ve brought us joy, but that makes up for the fact that you lied to us and we spent all this money. Let’s see… Fagin in Oliver. Let’s say Fagin. That would be delicious. I’ve picked a lot of characters with really wordy songs, and that’s kind of all villains.

Do you feel like I Want To Be Your Man is a show for everyone or do you have a specific audience in mind?

I expect different people to get different things out of it. Because I date a writer, I have a lot of conversations about multi-dimensional female characters, and so I think someone that is a writer might see it and think, oh, these are just human stories. Anyone has access to all of this. I do hope it helps other women in the industry to own their power more. If I can contribute to that in myself or in anyone else, I mean, what a gift.

I also want people to know that they are going to come and have a very good time. It’s going to be silly. It’s going to be loud. It’s going to be exciting and fun. It’s not preachy. It’s an exploration and celebration of this really fun music. I do hope that no matter what, they have an enjoyable hour of their lives and they leave having laughed and heard some kick-ass musicians play the hell out of a venue.

How can people get tickets for I Want To Be Your Man?

Go to 54Below.com. The show is May 12 and 14, and if you want to find out more about She’s The First, it is ShesTheFirst.org. They are also on all social media, and it’s great because they share a lot of pictures and personal stories of individual girls. You can see the way they are impacting lives.

Where can people find you online and catch up with your latest projects?

I’m at AmyJoJackson.com, and you can also find me on Instagram, and Twitter, Facebook, and YouTube.

Tickets are available for I Want To Be Your Man online and through the 54 Below box office. There is a $25 food and beverage minimum for the show. Doors open at 8:45 PM on May 12 with a 9:30 PM starting time, and doors open at 11:00 PM on May 14 with an 11:30 PM starting time.