Jessica Sherr On The 5 Things You Need To Create A Highly Successful Career In Film, Off-Broadway, and Live Performance Art

Yitzi Weiner
Authority Magazine
Published in
19 min readMay 31, 2024

Take Care of Your Mental Health: Journal, meditate, and practice gratitude. The world is a strange place with a lot of unrest, and as a creative person, it’s crucial to maintain inner happiness to create ongoing work. Burnout is real, so take 15–30 minutes each day, preferably in the morning, to take care of yourself. This inner care will reflect in your external work.

I had the pleasure of talking with Jessica Sherr. Jessica is a multi-talented actress, writer, and producer based in New York City. Known for her infectious and vibrant personality, Sherr has made a significant impact in the entertainment industry with her dynamic performances and creative storytelling. Her one-woman show, Bette Davis Ain’t For Sissies, directed by Drama Desk Award-winning Karen Carpenter, has earned international acclaim, marking a high point in her career. The show debuted at the Edinburgh Fringe Festival and went on to enjoy a successful run at St. James Theater in London, followed by two four-week runs in Chicago, and over 400 performances across 30 states and three countries. Sherr’s portrayal of Bette Davis was so compelling that the Bette Davis Estate gifted her with a pair of Davis’ scarf, gloves, and earrings to wear during her performances.

In addition to her theatrical success, Sherr has made notable appearances on television, including roles in Claws (TNT), Cloak and Dagger (ABC FreeForm), and Blue Bloods (CBS). Her versatility as an actress is evident in her ability to seamlessly transition between drama and comedy, captivating audiences with her on-screen presence. Sherr has also made her mark as a producer. Her Award-Winning dark comedy Wicked Image has earned her multiple accolades of Best Comedy Reedy Reels Film Festival, Austin Under the Stars, Borrego Springs, Baltimore Next Media, and Best Director at the Woman in Comedy Film Festival in Atlanta. It has been screened at esteemed film festivals such as the Lighthouse Film Festival, Beaufort International, and Block Island Film Festival, earning her the titles of Best Short Short Comedy at the Cutting Room International Film Festival. Jessica’s work on the award-winning web series, Scratch This, has earned her recognition and numerous accolades. The series has been honored as the Best Web-Series at the Garden State Film Festival and has received the prestigious Best Ensemble Cast award at the Bilbao Seriesland & Miami Web-fest.

Born and raised in San Diego, Sherr’s passion for performance was evident from a young age. Her mother recognized her talent and enrolled her in tap dance classes at the age of three, where Sherr developed a love for performing. Her early experiences in children’s theater, including roles in The Wiz and productions at Starlight, an outdoor theater in San Diego, solidified her desire to pursue a career in the arts. Despite facing setbacks, such as not being accepted into the Bachelor of Fine Arts program at UC Santa Barbara, Sherr’s determination led her to New York City, where she has been thriving for over two decades.

Sherr’s dedication to her craft is complemented by her extensive training with Wynn Handman. She is currently studying with esteemed acting coach Glenn Morshower and studies in improvisation at renowned institutions like the Upright Citizens Brigade (UCB) and The Peoples Improv Theater (The PIT). Beyond her artistic pursuits, Sherr is a certified personal trainer and holds a real estate license, underscoring her commitment to personal growth and physical fitness.

Her journey in New York began with theater roles and independent film projects, which laid the groundwork for her subsequent success in television and film. Sherr’s breakout role in the independent film, Where Are You Sophia, alongside well-known actor Corbin Bernsen, introduced her to the world of independent filmmaking. This experience, coupled with her work in theater, has shaped her career and allowed her to develop a unique voice as both an actress and a writer.

Sherr’s one-woman show, Bette Davis Ain’t For Sissies, not only showcases her talent as a performer but also highlights her skills as a writer. The show, which delves into the life and struggles of the iconic actress Bette Davis, has resonated with audiences worldwide. Sherr’s ability to embody Davis’ spirit and determination has earned her widespread praise and recognition. Her feature film script, BETTE, based off her solo show, is co-written with Caitlin Scherer Top 5 Comedy Finalist at Austin Film Festival, was a finalist for Screen Craft and Scriptapalooza and placed in the top 10% of the Nicholls Fellowship.

Looking ahead, Sherr is involved in several exciting projects. She continues to tour with her one-woman show, bringing the story of Bette Davis to new audiences. Additionally, she is working on a new feature film project with filmmaker Chandler Wild and Scott DeLaCruz, titled Hilary Quick Doesn’t Talk to Her Anymore, Semifinalist Austin Film Festival and set to film in 2025. Sherr is also in the process of producing and starring in a feature film adaptation of her Bette Davis script, aiming to bring the legendary actress’s story to the big screen.

Sherr’s fearless approach to taking risks, her passion for storytelling, and her ability to connect with audiences make her a standout figure in the entertainment industry. With her star on the rise, Jessica Sherr continues to captivate audiences with her talent, humor, and dedication to her craft. As she ventures into new creative endeavors, Sherr remains committed to bringing compelling and authentic stories to life, both on stage and screen.

Jessica, It’s a delight and an honor to meet you. Before we dive in deep, our readers would love to learn about your personal origin story. Can you share the story of your childhood and how you grew up?

I started off as a young creative person. At the age of three, my mom saw great talent. She put me into tap dance classes. I was little and always the smallest one in the class, so I’d be on the end of all the dance lines. You have the tallest girl in the middle and the shortest on the ends. I’d have to travel across stage with my little legs. And I remember how seriously I took my role of getting across the stage quickly.

I was very passionate about my tap dancing. I got the bug when I was tap-dancing Snowman. I knew at that moment, on stage, seeing the audience and feeling their excitement, that I was meant to be a creative person. My mom has always been very good about supporting my creative side. I was a quirky kid, always having big ideas. I remember being on the playground with crazy ideas of building a fort or a castle and she’d always say, “Let’s do it!” She was really good like that.

I feel my mom has been a huge supporter of making sure my ideas get translated. She saw that the dancer in me turned into being really good at doing theater, so she found a creative arts school called F.A.M.E in San Diego. Theater opened up this world of creative arts that I hope every kid gets to experience. It’s a place where you find yourself when you don’t fit in. There’s a place there where you can dream big with other kids who are similar. Together, you can build a story or a theater production that’s exciting and feels very alive. That’s where I started.

Amazing. Can you share with us the next chapter of that story? How did you get your first break in entertainment and how did your career develop?

What happened was I started out in San Diego, and luckily, San Diego, California has a really great theater scene. If you’re a theater person there, you have children’s theater. One thing I did was called Junior Theater, and Junior Theater was fantastic. They would take regular plays and have kids perform in them. One of my first plays with them was The Wiz, and I was part of the Yellow Brick Road. It wasn’t a big speaking part, but I got to dance with three other Yellow Bricks, and we became the best of buds. It was so fun to have rehearsals together, and that kind of gave me confidence to go to something called Starlight, which is also in San Diego. It’s a very famous outdoor theater.

The way that Starlight works is, because it’s outside and San Diego has a very active airport, you have to freeze whenever a plane flies over. So, if you’re on stage and there’s a plane, you watch these little lights go yellow, and then green, and you have to stop. It was really in the moment and very cool. That was the coolest thing, being part of a Starlight play. Then I went to college at UC Santa Barbara. Sadly, I didn’t get into any of the theater programs. I got into what I would call the academic side of theater, but I actually auditioned twice for their Bachelor of Fine Arts program and didn’t get in, which was what I really wanted to do. It set me back, and I had four years of not really getting to do what I love.

So, I bought a one-way ticket to New York City because I had these big dreams of making it there. I thought, if you can make it here, you can make it anywhere. I took that frustration of not being able to do what I wanted and said, “I’m going to get so good in New York that I can go anywhere I want.” I’ve been in New York for 22 years now, a long time.

How did New York change your career? How did it put your career on a different trajectory?

Because the weather isn’t as warm as San Diego, it made me work really hard. I had more time, like during winter, you can’t always be outside on the beach just hanging out like you do in San Diego. I fell in love with the drive people have here. People ask if I’ll ever leave, and I say I love the drive. If I can find a place that has a drive like New York City, then absolutely, but I love that people work really hard here. You can create and be supported by others in New York. It’s not just, “Oh, I’ll get to you tomorrow.” It’s like, “Okay, what do you need? How can we support you?”

I started in theater here, and then I got my first independent film role that I auditioned for, like everyone does. It ended up being with a well known actor named Corbin Bernsen. That was exciting because it taught me about independent filmmaking and being in an independent film, which is very different from Hollywood. Like everyone, I got my agents, and I got my first feature film where I was in the movie Annie (Columbia Pictures). That was cool because friends recognized that I was in a major feature film. Then I got into auditioning for film and TV, and now my film and TV life is balanced with my theater life.

I wrote a play back in 2008. People said I looked a lot like a woman named Bette Davis, a very famous 1930s actress. Someone dared me to write a solo show, so I did. I ended up writing a show about Bette Davis’ life in the 1930s. It became a huge success. I did it in New York at the New York Fringe Festival, then took it to Scotland at the Edinburgh Fringe Festival three years in a row, where I sold out my 100-seat audiences. It was phenomenal. I got a run at the St. James Theatre in London because an audience member called and said the show was so good, they must bring Jessica over. I reached out to the Bette Davis estate, and they gave me a pair of Bette’s scarf, handkerchief, and gloves to wear in the show. It’s been blessed.

I had two runs in Chicago, both four-week runs. A theater there had seen a piece of my show and thought it was interesting. They wanted to champion playwrights, so I got to do a run in Chicago twice. Then I started touring with it and performed over 400 shows in Performing Arts Centers around the country. Little did I know, the snowman Jessica would get her due diligence. It’s just me on stage, performing a full show about this well-known actress who fought against the Hollywood movie moguls. It’s been one of my greatest joys because it’s brought me a lot of confidence to know that I can write and perform.

That brought me to realize how much I love producing as well, which led me into my other life — producing independent films. I wanted to be able to do really good work. Bette Davis has been such a success, and I realized I want to play more characters. A few years ago, I produced a dark comedy film called Wicked Image. It’s about Lucifer, Satan, and the Devil meeting with a corporate PR agent to rehabilitate their images — which includes reminding the world that they’re women. However, they quickly discover that the PR agent is more evil than they are. I play Satine, aka Satan. It’s this joke on society not realizing the devils are actually women and also about how bad humans have become with corporate greed. It’s similar to Bette; it’s a woman’s story fighting against society. I seem to be drawn to these kinds of works and characters.

Wicked Image has been successful. I’m on the independent film circuit now, and we’ve won Best Comedy Performance at Borrego Springs International Film Festival, Best Comedy at Reedy Reels Film Festival, Best Comedy at Baltimore Next Media Film Festival, Best Comedy at Austin Under the Stars Film Festival and our director won Best Comedy Director at the Women’s Comedy Festival in Atlanta. It’s a funny film and glad audiences are enjoying it..

So I usually ask this question at the end, but I’ll ask it now: how would you compare and contrast your personal character with the character of Bette Davis? How are you similar, and how are you different?

Yeah, I think there are some similarities in that we’re both strong-minded and determined. We both love to do really good work authentically. I’m not someone who will ever dial it in. I will work really hard until I know I’m ready to perform or present something. I think Bette was the same way. We’re both stubborn in that sense. We don’t like mediocrity and don’t feel that dialing things in or being mediocre is the sign of a true artist.

I fell in love with how strong Bette was. When I read her book, The Lonely Life, It really showed how smart she was. I thought, “I wish I could have a mentor like Bette Davis.” When I said that to myself, I never knew my show was going to be so successful. It’s really been interesting how we’ve complemented each other. I think she’s kind of picked me because most people who play Bette play her like drag queen Bette, but I play young and plucky Bette Davis. So, we complement each other very well.

I have a feature film script called Bette that I’ve written with a co-writer, Caitlin Scherer. We worked on Wicked Image together. We wrote a feature film script to champion this trailblazer. I will play Bette Davis on the big screen as my next incarnation.

Can you share with us the exciting projects you’re working on right now and what you hope to be working on in the near future?

Yeah, yeah. Wicked Image has done very well on the indie film festival circuit. Often at film festivals you see dark content, but Wicked Image is bright, funny and stands out. People love it and it’s created a dialogue for me to connect with new audiences and meet so many filmmakers.

I met a filmmaker in Borrego Springs, Verve a Reposar, and we both love each other’s style. We’re working on another dark comedy together. We’ll write it and shoot it over a weekend this summer. It’s based on the idea that the Goddess Aphrodite loses her ability to love and her goddess friends must find a way to bring hope back.

Bette, our feature film is currently in Hollywood with a producer who is actively pitching it. When all goes well, it will be me on the big screen playing Bette Davis.

I met two filmmakers, Chandler Wild and Scott DeLaCruz, at the Block Island Film Festival. They have a feature film script, Hilary Quick Doesn’t Talk to Her Anymore. It was a semi-finalist at the Austin Film Festival this year. I read it and really loved the concept. I’m going to help produce it and I’ll be playing one of the characters in the film. We’ll be filming Upstate New York to take advantage of the tax credits. And start Spring 2025.

You’ve been a successful actress, filmmaker, and have many other talents. Can you share with our readers the five things that you need to create a successful career in Hollywood?

Here are the five things that I think are essential for creating a successful career in Hollywood:

1. Create Something for Yourself: Make a calling card that you truly believe in and can stick with for a long time. For me, it was Bette Davis Ain’t for Sissies. I wrote it, and it’s been a 12-year project that brought me 12 years of success. It gave me the confidence to present it and put me into the world of good actors who can collaborate with others.

2. Set a Due Date: Create something with a deadline. The New York Fringe Festival and the Edinburgh Fringe Festival gave me specific times to prepare and perform. Artists should set a due date, whether it’s for an open mic next Tuesday or any other event. Put it in your phone and don’t let anything get in the way of it.

3. Start Small: Take small steps, like joining an improv class at UCB or The PIT. Commit to six classes and show up. Embrace the concept of failing forward. Every time you fall, you learn and pick up something valuable. When I reached out to the Bette Davis estate, they provided me with personal items of Bette’s for my show. If I hadn’t written the show, I wouldn’t have had the courage to do that.

4. Utilize Accessible Resources: Understand that it’s very accessible to make a short film. You can do it in two days with a small crew and a modest budget. Good lights, sound, script, actors, and a dedicated space are all you need. I wish I had known this earlier, as it would have given me more creative energy and ongoing projects. With film, you can send people a link and have your work seen, which is harder to do with live theater.

5. Take Care of Your Mental Health: Journal, meditate, and practice gratitude. The world is a strange place with a lot of unrest, and as a creative person, it’s crucial to maintain inner happiness to create ongoing work. Burnout is real, so take 15–30 minutes each day, preferably in the morning, to take care of yourself. This inner care will reflect in your external work.

Is that enough? (Laughs)

It’s been said that sometimes our mistakes can be our greatest teachers. Do you have a story about a humorous mistake that you made when you were first starting out and the lesson that you learned from it?

My greatest mistake, hmm… yeah, not getting into the Bachelor of Fine Arts program in college. When I was at UC Santa Barbara, I had coached my monologues with the head of the drama department. Years later, after I had moved to New York, he emailed me on Facebook. He said, “I’m so sorry. The talent you are now is not the talent we saw. I’m sorry that we held you back in college.”

I realized that if I hadn’t had the gut to keep going, I might not be as gritty as I am now. Mistakes create a lot of grit, and you need grit because you need to be able to say to yourself, “You know what, I fell forward, but I’m getting back up.”

When I first wanted to go to Scotland, I had no money. I was thinking, “What am I doing?” One day, by accident, my roommate talked to a guy who worked for an advertising company. They needed people to talk about toothpaste. She came home and asked if I could answer five questions about toothpaste, so I did. The world is such a wacky place — I ended up getting a class A commercial for Aquafresh. It paid me enough money to go to Scotland three times, hire a real director, and pay for a publicist. I didn’t mean to do it; it just happened.

Sometimes, what seems like a failure is just the universe working in a funny way. You need to create grit for yourself because it strengthens your spine. When I first did my Bette Davis show in 2011, I got bad reviews. It took me a long time to get over it. I remember thinking, “How could people be so mean?” I had to remember that not every review matters. The best thing you can do is know that a review is just one person’s suggestion and criticism, but it’s not who you are. Never read reviews during a run. Now my reviews are stellar, but it took me a long time to figure that out.

There was a point where I wanted to give up because it felt so wrong. I was spending so much money on this play, thinking, “What am I doing? It’s not bringing me direct success, but it’s doing something.” So, long answer answered.

Yeah, that’s a good answer. I’m really happy you pushed forward. I probably would have stopped if it were me.

I mean, there were so many times I wanted to stop because it was just so difficult. Here’s another wacky story: I was doing the show and did a little 15-minute showcase of my Bette Davis show out in Milwaukee to try to get theaters to pick it up. That’s what I do. I go to places outside of New York for booking conferences, and you never know who’s going to pick it up. So, a guy from Chicago saw it and said, “I really like your show. Do you want to come to Chicago? I’ll give you four weeks and a theater.” That had never happened in New York. I was shocked.

When I went to Chicago, I wasn’t fully ready. I had just gotten back from Edinburgh and it wasn’t fully ready for a critically acclaimed run, but I did it anyway. During my third week, he said, “I really like your show, but I think you can expand it. Come back in a year and do it again.” So, I spent a year expanding the show and came back. That was the first time I really felt validated. Both the show and I were reviewed really well.

The second time I performed in Chicago, I got to expand the show in a way it didn’t have before. It wasn’t just about the star Bette Davis; it showed her underbelly, her life at home, her failed marriages, her strained relationship with her daughter. It showed her failures. That was hard because when I first presented it in Chicago the second time, I had no idea if it would be liked. It was a tough process, but as an artist, you just have to go through it. It’s not all going to be roses, and most of it isn’t, but that doesn’t matter. You still have to go through it.

From all that success, I gained confidence in the show. I started touring in performing arts centers, anywhere from 500 to 1000 seat theaters. I now have a Drama Desk Award-winning director, Karen Carpenter, who’s amazing. I wouldn’t have had the confidence to ask Karen if she would help me without all those trial and error experiences out of town.

Before COVID, my plan was to redirect the show and raise enough money to do it Off-Broadway. That’s still going to happen. Because of COVID, I didn’t get to raise the money as planned. In New York, to have a success, you need investors. It will happen because the show truly deserves it. I wouldn’t have had the confidence to ask Karen to come on board without those experiences. She’s an amazing director who brought the life to the show that I, as an actress and writer, couldn’t achieve on my own. Actors shouldn’t direct themselves unless they really know what they’re doing. You need an outside eye to help you get to the next level.

Producing is different. Producing is more about setting things up, like how we arranged this call. Directing is like telling me what to do. Producing, directing, acting, and writing are all different brains. I found out that I’m not a good director because it keeps me in my head. I had to realize that while I was on stage, I was critiquing myself instead of just acting. I needed someone better than me, and that was Karen. I reached out to different directors, and Karen was the only one who said she didn’t want to change my show, just make it better.

Producing gives actors power. When I produce, I hire the people I want on my team. If I make a mistake in hiring, I can move on. Producing allows you to have full control over the final product, like editing and color correction. As an actor, you don’t have that ability. It’s a strange career because you’re not allowed in certain rooms until you’re at a certain level or until you do your own thing.

It’s fascinating and mind-blowing when you think about the different levels. No one tells you this in college or acting school. They don’t tell you that your career is based on what others see you do in auditions or performances. It’s a very slow process, often a 20-year overnight success. After 20-some odd years, people might say, “Oh, you’re doing so well,” but it’s been a long journey.

Jessica, because of the platform that you’ve created and the work you do, you have enormous influence. If you could spread an idea or inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Oh wow, I would love to see something like they do in improv, where you learn to say “yes, and” in a healthy way. I wish people would listen to each other more and collaborate in a way that brings joy, happiness, and laughter. Sometimes I feel like there’s less laughter to be had these days. The idea of family is changing, and the world feels more disconnected than connected. If there was a way to create a space of joy where people could come together and laugh, a movement of laughter that heals, I think we really need that right now. We need a platform for healing.

That’s beautiful. How can our readers continue to follow your work and support you? How can they purchase anything that supports your work?

There are a couple of websites as well as social media. My personal website is

www.JessicaSherr.com,

For the show dates and tickets, www.bettedavisaintforsissies.com. You can watch the show on Tubi, rent it on Broadway Demand, or come see a show in New York.

I have 5 shows in New York at The Triad Theater on West 72 June 20, July 16, Sept 12, Oct 20, Dec 15

The Bell Theater in New Jersey Oct 19

Montalvo Arts in California on Nov 14th

As an independent artist, I am a 501(c)(3), so you’re welcome to donate. During COVID, I did live Zoom performances from my living room every other Thursday, and people from around the world would watch and donate. People were incredibly generous. If anyone wants to donate, Venmo @@jessica-sherr Zelle jessica.sherr@gmail.com or PayPal.me/jessicasherr

My Instagram is @jessica_sherr @bettedavisaintforsissies I’m always on Facebook too.

I’m doing the show in New York at a theater on the Upper West Side. I’ve decided to do it once a month, and the show has been phenomenal.

Well, it’s been so nice to meet you. I hope we can do this again next year.I hope all your projects blow up in a good way, and you win all the awards.

Thank you. Thank you for your energy. I really appreciate it.

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Yitzi Weiner
Authority Magazine

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator