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Gwen Hollander: “How would it feel if I were them”

Keep your eyes on your own page. Everyone’s journey is going to look different; this career is not necessarily linear. This has always been a very big struggle for me, and social media makes it so much harder. It takes a lot of discipline! As a part of our series about pop culture’s rising stars, […]


Keep your eyes on your own page. Everyone’s journey is going to look different; this career is not necessarily linear. This has always been a very big struggle for me, and social media makes it so much harder. It takes a lot of discipline!


As a part of our series about pop culture’s rising stars, I had the distinct pleasure of interviewing Gwen Hollander.

Gwen Hollander is an actress, singer, and writer who can currently be seen in Showtime’s Kidding and Hulu’s Future Man. She spent the first part of her career in New York working in musical theatre. She now resides in Los Angeles with her husband and their two dogs!


Thank you so much for doing this with us Gwen! Can you tell us the story of how you grew up?

Thank you for having me! I was born and raised in Miami, Florida, with an older brother. I had a pretty standard childhood, I think! I was always into the arts…it started with piano lessons, then dance class, then school plays and voice lessons. By the end of middle school, I was pretty much spending all my free time working on those kinds of things. I went to an amazing performing arts high school (New World School of the Arts), and then after that, I went to The Boston Conservatory. I left after one semester, though! One of the amazing things about my high school is that there’s also a college program, and for our art classes we had the same professors and, essentially, the same curriculum as the college students. So, I’d basically had a college conservatory education, and then I went to another conservatory! I knew I had so much more to learn (I mean, we’re never done learning anything, ever!), but my parents actually suggested to me that I try just moving to New York…It was hard for me to process because I was extremely academically oriented in school and it seemed crazy that I would “drop out!” But I do think it was the right move, for me. By no means do I endorse skipping college and heading straight to NY or LA! It just happened to be the right thing for me to do, given my specific circumstances and the choices I had made up to that point. Had I chosen to go to a liberal arts school I may have stayed!

Can you share a story with us about what brought you to this specific career path?

I was always into performing as a kid, but my real “aha” moment was when I was 13 and went on a field trip with my 8th-grade drama class to see the touring production of The Phantom of the Opera. It wrecked me. I couldn’t get up from my seat when it was over; I was just sitting there staring at the empty stage. The ushers finally had to move me along! I decided that night that I was going to do this. I went back and saw it several more times while it was in town, and my dad managed to get me backstage to meet the actor who played the Phantom. I ended up writing him letters for the next few years (he was very sweet and wrote back and also sent me signed production photos that are still hanging in my childhood bedroom in Miami. Years later a friend of mine was working on a show with him and I told her this whole story, and he called my voicemail and left a message singing “Music of the Night” from Phantom. It was such a full-circle moment because at that point I was living in New York and working professionally as an actor!). I was just so profoundly moved by that experience in the audience of that show… I still can’t really put my finger on it. But I think most actors have that show they saw that flipped that switch, for whatever reason.

Can you tell us the most interesting story that happened to you since you began your career?

This feels so overwhelming because this career is really just a series of interesting moments! Sometimes when I try to think of stories I just draw a blank, even though I know there are SO many. But as I thought about this, I think I’d say the story of how I met my husband is pretty interesting, just in terms of the connections you make in this business and how things line up in miraculous ways. I was living in Los Angeles at the time, and I got an email one night from a friend I had been in a sketch group with a few years before…he had written a musical that was about to have its world premiere at a very prestigious theatre in the Berkshires, and they had just lost an actress to a big job, and they thought of me and were wondering if I might be able to fly out a few days later to start rehearsals. It was totally out of the left field, I was shocked that they’d thought of me… I hadn’t seen them in years. I wasn’t really pursuing musical theatre anymore and had no interest in going back to NY…and I’d have to book my own travel because it wasn’t in their budget to have an out of town hire; they only had the budget for the actress they’d already cast, who was local. And I knew nothing about the show (I knew how talented my friend was, but I didn’t even know what I’d be doing) and I had a whole life and plans and commitments in Los Angeles…but I said yes. On the first day of rehearsals for this show that had come out of nowhere three days earlier, I met my scene partner, who is now my husband. And it’s not just that; people meet their significant others in shows all the time! It is that both of us had just gotten out of very serious long-term relationships and neither of us had any interest in meeting anyone at that time. And also that we ran in all the same circles; we had all the same friends (from when I was living in NY), and we should have met dozens of times, but we never had. He knew who I was, and I had heard of him before, but I didn’t even realize it until much later. It was one of the only times in my life that I’ve truly believed in “fate,” and that there are certain places you’re supposed to be at certain times. The composer of that show and his wife, who was an actress in the show and was also in the sketch comedy group, performed our wedding ceremony because they were the reason we met!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Oh, I’m sure I made all kinds of silly and embarrassing mistakes… I don’t know why I’m drawing a blank on specifics; maybe just because you try to block those things out? I’m sure I got in over my head a lot by saying what I thought people wanted to hear… like, “are you a dancer?” (I can “move well,” as we say in musical theatre, and I’ve taken a lot of dance throughout the years… but I am NOT a “dancer” in the way someone means when they ask that). And there were times when I said “yes!” and then found myself in a dance call with DANCERS. Which is a humiliating experience that feels like the longest 45 minutes of your life, and you wish you could melt into the floor. So, I did a lot of things like that, and the lesson I learned is to NOT DO THAT! I’m very honest about what I can do and what my weaknesses are. In the world of TV and film, they often ask you about certain skills and take your word for it, and then you show up on set and are expected to do it (no one has time to find out if you can really ride a horse or play varsity level softball). Lots of people are going to be pretty angry if you show up and admit that you rode a pony at a birthday party when you were 5 or played T-ball in elementary school!

What are some of the most interesting or exciting projects you are working on now?

Well, right at this very moment everything’s kind of on pause within the industry as we practice social distancing… so I don’t exactly know what’s next! I’ve been working on a project from home that’s been a lot of fun; I wrote parody lyrics to a bunch of songs from “Avenue Q” and have been putting together videos from footage that my friends in Los Angeles and New York have sent to me. I’ve been posting them in conjunction with fundraisers for The Actors Fund (they’re raising money to help all the artists who have found themselves without work because of the pandemic), and we’ve actually raised a lot of money so far! So that’s been fun, and also feels good. I also work on a show with my husband and some of our friends called “The Astonishing Show Show,” which is a live show featuring puppetry, magic, music, and comedy. We perform every other month at a theatre in Los Angeles, and it’s so much fun and so satisfying. I’m really starting to enjoy creating my own stuff, and it took a long time for me to get there; I was very resistant! But starting is the hardest part. Once I got into the groove, I really enjoyed the process. It is so gratifying!

We are very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in film and television? How can that potentially affect our culture?

It’s so important for so many reasons. One reason is that it’s vital for children to see themselves represented in the stories being told (adults too, of course, but ideally that kind of exposure starts at a young age so that a person grows up feeling like a member of society and not something “other”). So much of what we absorb about the world is through the stories we’re told, and we consume the majority of our stories through film and television. If someone isn’t seeing themselves reflected in those stories, what does that lead them to believe about themselves and their place in the world? Everyone should see everyone co-existing in all the stories, because that’s how it should be in real life. It’s a shame that it is something we even have to think about and that it doesn’t just happen naturally, but I’m glad the conversation is finally being had.

Another thing that I think is important is that we don’t just shoehorn diversity into the same old stories we were already telling, just for the sake of optics. Sterling K. Brown spoke about this so beautifully in an interview a few years ago, how so much of diversity on TV is that a character just “happens to be diverse.” But he loved that his ethnicity was part of his character’s story as the adopted child of a white family; it wasn’t a character that just happened to be black. He was telling a story that was specific to the black experience. And that goes back to the first thing, about people seeing their experiences reflected, so they know their experiences matter. And maybe they felt alone in that experience and see that they’re not! I felt the same way after seeing “The Farewell;” I had never seen a movie released widely in the U.S. that was so unafraid to just tell a Chinese story and not whitewash it in some way (that’s not to say there hasn’t been one; it is just the first one I’d seen!). The movie trusted that the audience wanted to see that story, and we DID! I want to learn about other cultures and experiences, and I don’t learn about other cultures merely by seeing someone from another culture onscreen. I want to know their stories! So, this part extends beyond the actors; we need more diversity from the writers and directors, too. And we need more female voices, too, on all sides!

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

Keep your eyes on your own page. Everyone’s journey is going to look different; this career is not necessarily linear. This has always been a very big struggle for me, and social media makes it so much harder. It takes a lot of discipline!

It’s going to be very hard! It’s a long game and, again, it’s not necessarily linear. There are times when you get a job and are tempted to think “oh my gosh, this is it! It’s happening! Now it’ll be easy!” But it won’t ever be “easy,” because even if every door were to open easily for you (which I guess maybe has happened for some people, but it’s never been my experience), you still have to work hard so that you’re prepared to meet that opportunity at your best. And yes, you work hard to get the role, but then once you’ve got it, you then have to do it. And do it well! Which leads me to…

Your work is never done! You’re never done learning. There’s always something to work on, and there will always be something you’ve never done before, whether it’s a type of role or a specific skill. I worked on a film a couple of years ago where I was supposed to play the guitar, or at least look like I was playing the guitar. I took lessons and worked very hard on my own in the limited pre-production time we had…but I still wish I’d worked even harder to make it look even better. I did the best I could in the amount of time we had, but this kind of thing pops up all the time, and it is part of our job to always be learning.

Ask for help. Whatever that may mean for you. It might mean support from friends; it might mean going to therapy. I know some people feel like it’s a sign of weakness to ask for help or go to therapy, but it’s actually a sign of great strength to do what you need to do to take care of yourself. This business can be cruel and inhumane, and therapy has helped me to just accept that fact and not try to normalize it, and not think that something’s wrong with me because I get frustrated and sad sometimes. It’s hard, but I chose it! So, if I’m going to continue to choose it every day, I might need some help!

Just make your own work. People had been telling me this for years before I finally did it. I was resistant for lots of reasons, but a big one was fear. What if it wasn’t good? What if no one cared about what I had to say? And honestly, it may not be good, and people may not care! The key is to be doing it for you, which is really hard to wrap your mind around… and again, I struggle with this every time I start a new project. You just have to start.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Find other things you love to do. This is hard because there’s the school of thought (to which I have always subscribed) that says “give it everything! Work so hard and think of nothing else, and then you’ll be undeniable!” And yes, we should always be working hard. But because this business is not necessarily a meritocracy, if you don’t have something else in your life it’s very easy to feel bitter and angry. There are a lot of factors that we can’t control, so even if you give it 100% of your focus 100% of the time, you still might not see the results you had hoped for. So let yourself feel burned out; it’s human! Then find the thing you can do that you know will make you feel good. And then, once you’ve recharged, you can get back to work!

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Well, I think one of the biggest societal problems we have is a lack of empathy, and I think I would somehow want to tie that into my love of animals. I think animals (both domestic and wild) can teach us so much about kindness, empathy, and maybe more exposure to/education about conservation and regard for animals could help foster that in people. I’m not sure exactly what that would look like, but I would be very interested in finding out!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I will always thank my mom first, for being the most supportive person on the planet. She was my very biggest fan and greatest cheerleader. She passed away just over nine years ago, which was devastating and left a huge hole in my heart. But I would also say my friend and mentor Dani Davis, who was always a mother figure to me, even when my mother was still here…she was my “New York mom” and then became a real mother figure to me once my mom was gone. She has supported me in all ways, but in addition to being a sort of surrogate mother, she also taught me SO MUCH about myself as an actor.

I first met her when she was teaching a class in NY; it was a musical theatre class that was, essentially, about song interpretation and auditioning. She taught me the value of being authentically myself, even when it is scary. As auditioning actors, we’re so focused on being who “they” want us to be that sometimes we forget to be ourselves and share what makes us unique. It’s literally the only thing we have that no one else has. If you’ve got 100 girls auditioning for the same role in a well-known musical, chances are you’re going to see 100 girls doing basically the same thing because that’s what we assume “they” want to see. And again, if it’s a well-known project, then we’re likely to recreate what we’ve already seen, because hey, that’s what they want, right? Well, I remember years ago I had an audition for the role of Eponine in the National Tour of Les Miserables (a dream role of mine which I had already played regionally but would have loved to do again). I went to Dani to coach for the audition, and I was supposed to bring in my own song in addition to singing “On My Own” (Eponine’s big song from the show). Dani said “Well, I think it’s obvious. You have to sing “Eye of the Tiger” (we had created a very funny audition piece where I sang the song starting as a very serious ballad and then it kicked into full-on Survivor/Rocky III mode halfway through; it had kind of become my signature song). I looked at her like she’d lost her mind, and she said “What? They said a song of your choice! Why wouldn’t you sing that?” I said, “Because they’re going to think I’m insane, or an idiot, or that I’ve never seen the show!” And she said “Or, they’re going to be so excited to hear something other than the heart wrenching teary ‘why doesn’t he love me’ ballads that they’ve been hearing for the past 6 hours. This is what YOU do. Show them what YOU do! Then sing “On My Own” and show them that. But introduce YOU first.” That was the audition philosophy she taught that was so valuable: Introduce yourself. Don’t try to be what anyone wants, just show them who YOU are. And go from there! As terrifying and counterintuitive as it felt, I sang “Eye of the Tiger” for that audition. And though I didn’t get the role (they were going in a completely different direction that had nothing to do with me), she was right. They asked what I was singing, and when I told them, they were surprised and super excited. They jammed and danced and tapped their feet through the entire thing. Then I sang my song about heartbreak. It was terrifying, and it still is, to show up authentically and not fall into the trap of “what do they want me to be?” But I will carry that with me, always.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Mine’s pretty basic. I’m all about the Golden Rule: Do unto others as you would have them do unto you. Treat others how you’d like to be treated. No one wants to be treated badly, so if we truly stuck to this, no one would treat anyone badly (or, if they did, they’d hopefully realize in retrospect that they wouldn’t have wanted to be treated that way and learn something from it). We all slip up and behave badly sometimes; it’s only human. But if we just look at things through that lens, the “how would it feel if I were them” lens, everyone would just be kinder. And it really shouldn’t be that hard to be kind!

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

I always say Tom Hanks, and I don’t even really have the reason why! It has just always been Tom Hanks. I’ve loved him since I was little, and I’ve just always wanted to hang out with him. I’d love to work with him, of course, but I’d be happy just to hang! There’s a reason why he’s one of the most beloved movie stars in the world…I think people want to be friends with him. And I’m no exception!

How can our readers follow you on social media?

Instagram: @gwenstagram811

Twitter: @gwennyh811

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