Jen Wineman
Interview Highlights
The world would be a better place if we all had a stronger relationship with our childlike imaginations.
Comedy is an incredible tool for accessing people’s hearts and affecting how they think.
It is helpful to find joy in pursuing a career in theater, not just in the successes.
Broadway needs to take more chances and expand the idea of what is “producible”.
Find Jen Online:
Website: jenwineman.com
Instagram: @winemanjen
Jen’s Current and Upcoming Work:
Bio
Jen Wineman (she/her) is a director and choreographer based in Brooklyn. Selected NYC credits include: Retraction (Theatre Row); Dog Man: The Musical (Lucille Lortel Theatre/TheatreworksUSA); Less Than 50% (59E59); Surfer Girl (Animus); My Heart is in the East (La Mama); Fable (NYMF); The King’s Whore (Walkerspace); F#%king Up Everything (Elektra Theater). Selected regional credits include: Tiny Beautiful Things (Merrimack Rep); Game On (Pittsburgh CLO); Shakespeare in Love (Virginia Rep); Into the West (Tantrum Theater); Baskerville (Dorset Theatre Festival); The Elaborate Entrance of Chad Deity (Asolo Rep & Miami New Drama); Sweeney Todd (Playmakers Rep); The 39 Steps, Shipwrecked (Triad Stage). Touring productions include Dog Man: The Musical (TheatreworksUSA); Twelfth Night and A Midsummer Night’s Dream (Asolo Repertory Theatre). Jen recently completed shooting a short film, Battle Rattle, written by Gardiner Comfort. Education: B.A. Vassar College, M.F.A. Yale School of Drama.
“Don’t save happiness for when you’ve ‘made it.’”
Meet Jen
Hayley: We are here with the brilliant Jen Wineman! Please introduce yourself, share your pronouns, and tell us a little bit about what you do in theatre.
Jen: My name is Jen Wineman, my pronouns are she/her. I live in Brooklyn, and I am a director and choreographer. I mostly do new work, and I love to live in the land of comedy.
Amy: Can you tell us a little bit about your journey?
Jen: I grew up doing theatre. Like everyone, I started out as an actor, because apparently, they don’t let you direct when you’re four. I was always in plays around my community and in school. But as a kid, theatre was just one of many activities that I did. For a while, I was convinced I was going to be an Olympic gymnast or a paleontologist, so I didn’t have a clear focus on theatre from birth or anything. When I was in eleventh grade, my school was doing Noises Off, and I tragically did not get cast. So I asked if I could be the assistant director. I didn’t know what that meant. I just knew that I would get to come to rehearsal and that I would get one of those priceless show T-shirts for everyone to sign at the cast party.
As it turned out, I got to do a lot on the show. I grew up in a house of Monty Python watchers, so even though I didn’t know it, a British farce with silly accents was right in my wheelhouse. Since I was a gymnast, the physical aspect of the play came very naturally to me. I remember helping to stage Act 2, which is all silent, all movement, and I had this Oprah “Aha!” moment where I realized that directing was my calling. I even remember saying to my mom, “Directing is so cool…it’s like I get to play all the parts!”
Two years later, I went to Vassar and majored in drama. The great thing about Vassar was that there were so many opportunities to make theatre starting in freshman year. So I was really lucky to be able to start directing right away, at age 18. I had no idea what I was doing, but that didn’t matter. The stakes were low, and we were all beginners, failing together.
At Vassar, I formed a core group of friends and collaborators, and after we graduated, we all moved to New York and started a theatre company called Studio 42. At first, the company focused solely on new plays by emerging writers. Eventually, it evolved into producing what we dubbed “unproducible” work. We did plays that playwrights couldn’t get produced for whatever reason – subject matter, technical requirements – we found a way to put on the plays for very little money and make them look fantastic. It became something that we were known for. Most of my early directing work in New York was with Studio 42. I didn’t realize at the time how lucky I was to get to learn and grow among friends in a semi-professional environment.
There came a point when I thought to myself, “I want to be able to do more than what I know how to do right now.” I loved working with young writers on new plays, but I wanted to expand my skill set and start getting hired by people who weren’t in my theatre company. I particularly wanted to learn about musicals, opera, and Shakespeare: things that I hadn’t had the opportunity to direct yet. I wanted to transition from directing being a thing that I did at night and on weekends to what I did for a living.
So I started looking at graduate schools and was very fortunate to get into Yale School of Drama. I had two big takeaways from my time there. The first is how much I love creating movement for the stage – and that evolved into doing formal choreography. And the second is that I find so much joy in creating comedy.
My aesthetic interests fall into a Venn diagram of comedy and magic. It could be literal magic like in A Midsummer Night’s Dream or just something magical about the play’s structure or the way the story is being told. I’m not necessarily the person to hire for a play where people sit on their couch and talk about how hard it is to be wealthy (although I enjoy seeing those plays when they’re done well!). Plays that take a lot of imagination and that feel impossible, that’s what I like to do. And if you sprinkle on top of that Venn diagram plays that deal with politics or race…then I’m truly at my best.
After grad school, I moved back to New York, and it was still a slog… But new doors started opening for me. I started getting interviews and meetings that I wasn’t getting before, and things slowly started changing. Momentum started to pick up as I booked more paying work, and I eventually started to have whole seasons of gigs lined up. Then I made the mistake of saying that 2020 was going to be my year and caused a global pandemic. I’m very sorry. (laughs)
About six months into the pandemic, when I was hungry to do anything creative, I started writing a book about directing and choreography. It’s called The Exploding Pot Roast (and Other Tales of a Moderately Successful Director). I’d always had ideas about what I would write about one day, but I thought that I couldn’t write a book until I won my first Tony. And then I realized that was silly, so I just started writing. The book is part comedic memoir, part how-to. It’s not “Here’s how you direct a play,” it’s more like, “Here are some things you might encounter when directing or choreographing in the American theater, and here’s how I dealt with those things.” It goes to a lot of interesting places. I need to get back to it, but it’s been hard since theatre has opened back up and I’m (thankfully) busy working again.
Jen’s Current Work and Creative Mission
Amy: Jen, what are you working on right now that you’re excited about?
Jen: I’m really excited about this new musical I’m working on called Starting Up. We just did a reading of it a few weeks ago. It is by Garett Press – he is the composer/lyricist/bookwriter, and it is a very hilarious sendup of the startup industry, which Garett worked in for a decade. The show is really goofy, but it wallops you at the end when the cast sings this song about how the internet brings us together and is creating a better world. It’s set in 2010–11 at the height of startup culture, and everyone is so hopeful that things can only get better from there…
I’m about to go down to Orlando to direct and choreograph the next tour of Dog Man: The Musical, which is the show I jokingly say I will be doing for the rest of my life. It premiered in 2019 at the Lucille Lortel Theatre and then went out on a national tour. The pandemic ended that. The most recent tour went out in January and just got back. This one is going to be a Florida/West Coast tour.
Amy: How would you describe your creative mission?
Jen: I like to use comedy as a way into people’s hearts and minds. When we’re laughing, we are much more receptive to new ideas and changing the way we think and feel about something. I love doing a show where you are laughing the whole time, and then you walk away with a message that you didn’t even realize you were being given.
An example of a show that I particularly loved directing is The Elaborate Entrance of Chad Deity. It’s a Pulitzer Prize finalist by Kristoffer Diaz. I did productions of it at Asolo Rep and Miami New Drama. This play has all the things I love in it. It’s a huge spectacle and contains feats of physical daring, and it’s also about race and politics and professional wrestling – which I randomly grew up loving. Chad Deity is an incredible meditation on race and privilege in America, and yet you are laughing the whole time. That is a show I would direct every year if I could. It encapsulates all the things we’re talking about. Everyone’s laughing, and everyone walks away with a gut punch.
Hayley: I love that.
Mentorship Experiences
Hayley: Jen, can you talk about influential mentors that you’ve had and what you’ve learned from them?
Jen: During grad school, Christopher Bayes was the most important mentor I had. He is a clown and commedia dell'arte master and a director in his own right. Studying with him helped me learn how to open up my heart and the hearts of the people I work with to allow “the little one to drive.” Chris gave me so much confidence in my ability to access my imagination quickly. Through working and studying with him, I developed my own improvisational style of working on my feet with actors, finding the funny and teasing out the juiciest bits. I try to infect the room with that energy so everyone feels free to pitch ideas or try weird things in an openhearted, generous way.
Hayley: Can you talk more about what it means to “let the little one drive”?
Jen: For me, theatre is all about imagination and harnessing that muscle that we all have, saying “It’s okay, flex this.” When we are kids, it’s so easy to play. All you have to do is jump up on a chair and you become a pirate. All the other kids immediately know that, “Yes, this carpet is now the ocean, and the couch is the island!” There’s no question. As we get older, we often push our creative muscles down and say, “That’s kid stuff. Let’s be serious. Let’s focus on being grown up and making money.” As if being creative and imaginative aren’t important. The world would be a much better place if we allowed that creative impulse we have inside to guide us instead of doing what we think we’re supposed to do because we’re adults.
Hayley: Amen to that!
Jen: That’s why I love doing things that people think are impossible on stage. Like in Dog Man, a cat wearing a robot suit needs to battle a bunch of giant buildings that come to life and are trying to destroy the city. All right, let’s go! Projects like that give me the opportunity to engage the audience’s playful spirits. To ask myself: What tools can I use to prick their imagination and make them fill in the rest of the story? To lean in and be a part of what I’m cooking up. When I can feel – forgive me for using this word – the synergy in the room and the moment of sharing that with the audience, it’s so exciting.
Amy: That’s my favorite part of theatre.
Benefits and Limitations of Womanhood
Hayley: Jen, how does womanhood fit into your identity, world, and experience?
Jen: It’s interesting. I’m a cisgendered woman. I’ve never questioned my gender or my expression of it. I’ve always felt free to show myself in the way that I’ve wanted to, which I know is not true for everyone. For a long time, I dealt with the sexism that I encountered by ignoring it and just pushing through. I realize that I unconsciously believed that talking about it would make it worse. That’s a very old-school feminist way of viewing sexism.
Amy: Right, if I’m tough enough to take it, then they’ll respect me.
Jen: Exactly. The idea that I won’t even acknowledge what’s happening because that somehow makes it real. Whereas if I just ignore sexism, I can press on. But I don’t think it’s effective, and I don’t think that helps other women. I’ve had experiences, especially in regional theatre, where I look around the table at a production meeting and every other person at the table is an older white man. I’ve had experiences where I get to the theatre on the first day, and I see that something’s been built incorrectly. And I’m telling these dudes, “We need to fix that. Let’s bring out the drafting. Why is what’s built different from what’s drawn?” That’s not necessarily something that men want to hear from someone who looks like me.
There’s this strange dance that I’ve had to do. As a leader, you have to empower the people you work with while also asking for what you need. But when women ask for what they need, they can get branded as demanding or difficult or worse. I’ve heard some pretty nasty things said about many successful female directors.
The fact is that a lot of people don’t want women telling them what to do. Full stop. Because of that, whenever I’m working with a new casting director, I always tell them that I want to fill the company with kind, generous actors who want to be directed by me. When I was 25, I was dealing with one set of things, and now that I’m not 25, it’s another set of things. Because I get to handpick my casts, it’s rare that I have a problem with an actor. It’s institutions that can be tricky. And it’s not always the men.
Especially once I became a parent, I’ve had to navigate and fight for what I need if I’m bringing my child to the rehearsal process. There was one theatre where I got an offer to direct and choreograph a production. My agent inquired about the three things he always asked about: a two-bedroom apartment, extra money to ship down some supplies, and whether the theatre had any resources for childcare. Over the years, I’ve encountered a wide range of resources. It’s been everything from, “We will provide you with a babysitter at no cost to you” to “Here’s a list of babysitters we love that other people have used.” And I’ve had theatres say that they don’t know and I’ll have to figure it out. My agent wasn’t implying that this theatre needed to provide anything in the way of childcare. The response was that the theatre rescinded my offer.
Hayley: That’s horrible.
Jen: And they told me point blank that they were pulling my offer because of me bringing my child.
Amy: That’s horrendous.
Jen: They said, “It seems like it’s gonna be too much for us to deal with. We don’t think we can accommodate you.” So I called the artistic director and said, “There are so many ways to make this work.” If your typical housing is a bedroom in a shared house, I just need two of the bedrooms. Or I would be fine with a one-bedroom if there’s a bed in the living room. You don’t need to provide childcare, we just wanted to know what you typically do to accommodate parent artists. About the shipping, I told him that my agent would usually negotiate an extra $200 to cover it. I assumed that they just needed clarification about what my agent was asking for, but the artistic director came back and said that it was impossible to make it work.
So I went full Gloria Steinem. I kept it professional, but I let the artistic director know that my “firing” wasn’t kosher. I let him know that he was making a strong statement about what kind of theatre they were and what kind of leader he was. I didn’t know yet that parents are actually a protected class. I just knew that what he was doing and saying felt wrong. Since then, Rachel Spencer Hewitt has started PAAL to advocate for parent artists, but at that time, I didn’t know what to do. I felt good about how I handled my conversation with him, but inside, I was furious.
The theatre had some internal conversations, and a few days later I got an email saying they’d figured it all out. They’d rescinded their rescinding of my offer! I did have the thought, “Should I go?” Maybe they’ve shown me who they are, and this is gonna be a nightmare. But at the same time, I felt like I had a responsibility to go and show them that it was, in fact, possible for a parent to also be a great director/choreographer. And you know what? Unsurprisingly, having my son there didn’t make things harder; it was fine. And the production came off really well.
Amy: Good for you, that’s a lot.
Hayley: That makes me so mad.
Jen: What’s great is that the leadership at a lot of theatres is changing. A lot of folks are retiring. And the ones who aren’t are learning a new way of being in the world. People are starting to speak up more. But I will say, my husband and I don’t put our kids on social media much. I don’t want people thinking, “Jen wouldn’t want this job because she’s a mom.” I did an interview for a show five days after giving birth to my daughter, and I felt that I couldn’t tell them the news because I didn’t want their decision to be about anything other than whether I was the right person for the job. So, yeah. Change is happening, but not all at once.
Amy: Jen, how do your gender and identity benefit you and the spaces you are in?
Jen: As a woman, it’s easy for me to make people feel comfortable. It’s easier for me to have gnarly conversations with actors because I have a non-threatening presence. If I’m choreographing intimacy, I can work with people and have really intense conversations and they’re not gonna get the wrong idea. Of course, I’m careful and aim to be as sensitive as possible. That doesn’t mean I’ve always gotten everything right, but I feel like I do have an advantage as a woman in that way.
When I did Chad Deity, it was an all-male cast and me. I remember thinking, “How’s this gonna go?” It turned out that bringing a female perspective to a show about a male-dominated industry allowed us to find nuance that I’m not sure they would have found with a male director.
I also think I’ve become a better artist since becoming a parent, because my time is more segmented. When I think back to my pre-kiddo life, it’s like I had all the time in the world. Now, my time doesn’t belong only to me. I’ll have a very specific time slot when I can prep for this interview or plan that rehearsal or send those 97 emails, so I use my time in a much more focused way. For me, time constraints yield much better results.
I love being a parent. But I also really love working. If I’m being honest, I would rather be in a rehearsal room than just about anywhere else. So every moment that I’ve spent working since having my son seven years ago, and especially since the pandemic began, I just feel so grateful to be in the room. I don’t take it for granted in the way I sometimes used to.
That applies to my social life, too. Getting to go out to dinner or drinks with a friend, having an actual date with my husband, I relish it. It’s my time. At first, I felt kind of oppressed by the relentlessness of the responsibilities that were added to my plate as a parent. But I’ve tried to flip the script in how I think about it. I get to go be in rehearsal for the next five weeks. There are all these things I need to do, but then in the afternoon I get to have three meetings about these upcoming shows. “I get to” instead of “I have to” has been an important shift for me.
Amy: That’s a great reframe.
Jen: It’s not always easy to do, but I try.
How to Improve the Theatre Industry
Hayley: If you could wave a magic wand and make a change to the theatre industry, what would it be?
Jen: Equity for all genders and all races. Easy answer. Also getting Broadway to take more risks on things that aren’t revivals and movie adaptations.
Hayley: “Unproducible,” perhaps.
Jen: Yes! Let’s do some unproducible shit!
Amy: Yeah! Expanding our perspective of what’s producible.
Jen: When you look at A Strange Loop, you would never guess that it would be a Broadway hit, and it is! When I first saw it Off-Broadway, I didn’t think it could move to Broadway no matter how great it was. I was thinking, there is no way tourists from Wisconsin are gonna get off the bus and watch this.
Hayley: But look, it’s happening!
Jen: Yeah, so I would like more of that please!
Thoughts on Work/Life Balance and Lessons Learned
Amy: How do you think about balancing your creative work with the rest of your life?
Jen: It’s funny because that’s a question that’s only ever asked of women. I don’t necessarily have a great balance. Most working parents don’t. The most important thing for my mental health and well-being is exercise. Not just for feeling good in my body but also being ready to choreograph and get on the ground in rehearsal. The emotional and mental gifts that exercise gives me only get more important as I grow older.
The thing that helps me is that even if I don’t have balance every day, I have things to look forward to that restore me again until next time. Like adult gymnastic classes with my husband or a night out with friends.
Hayley: Jen, what is something you wish you had known when you started out?
Jen: Don’t save happiness for when you’ve “made it,” because it’s human nature to constantly move the goal post for success. If you are always chasing something that is out of reach and saying, “I’ll be happy when…,” you’ll just never be happy. If you don’t find joy in the pursuit of this career, it is not your career. That does not mean you need to be ecstatic every minute of the day or enjoy getting rejected or having your emails ignored, but finding a way to be joyful within the pursuit makes it easier for things to come to you.
Also, go to therapy and don’t wait.
Final Thoughts
Amy: We would love to hear about what you are most proud of.
Jen: I’m proud that I’ve figured out how to make a career out of this. And I’m proud that I’ve had a positive impact on many of the people I’ve worked with as an artistic collaborator or as a teacher. That means a lot to me, more than people liking this show or that show. I’ll have actors tell me that I helped them reach a new level of what they do because of our work together. Those kinds of conversations mean the world to me.
Hayley: Thank you so much for sitting down with us, Jen.
Jen: Thank YOU!
