Veteran Actress Bess Armstrong On Thriving As A Woman Over 40 In Hollywood

Yitzi Weiner @ Authority Magazine
Authority Magazine
I’ve been doing this for a long time. The world has changed a lot, and so has our business. I mean, there were only three networks when I began, and television and features were two separate worlds. That sure has changed! One huge positive change has been the increase in diversity. I’m embarrassed and sad to think of how unaware we were decades ago about how underrepresented people of color were in our industry. I applaud that change. I think that women over 50 — maybe even 40 — are still discriminated against. I’m waiting for that to change but not holding my breath.

I had the distinct pleasure of talking to Bess Armstrong. A veteran actress, Bess has been working for over 40 years. Trained in the theater, she was discovered during a NYC casting call for a CBS sitcom called On Our Own. After a few years starring in television movies, she moved into feature films with Alan Alda’s The Four Seasons. Other films include High Road to China, Jaws 3, Nothing in Common, That Darn Cat, and Diamond Men. Among her dozens of television credits, the mini-series Lace and the iconic series My So-Called Life stand out. Bess can currently be seen on the Amazon series Bosch, and I Love That For You on Showtime. The daughter of school teachers, Bess grew up in Baltimore. She lives in Los Angeles with her husband, the movie producer John Fiedler. They have two sons.

Bess, thank you for joining us in this interview series. Our readers would love to get to know more about your background. Can you tell us about your origin story?

I grew up in Baltimore, Maryland. My mother’s side of the family is originally from Louisiana, but my father’s side has been in the area forever, which meant we had a lot of family members nearby.

I feel very blessed for the upbringing I had. My parents were madly in love with each other, content with their paths in life, extremely creative, supportive, intelligent, and just fun to be around. I grew up singing in three and four-part harmonies around the piano, had family dinners with animated conversations, lots of noise, pets, etc. The older I got, the more I realized how truly special that was because most people do not have that sort of family dynamic in life.

Both of my parents were teachers, but once my Mom had her fifth child, she decided to drop down to strictly substituting. Being a faculty brat was interesting because you always knew when students were talking about your parents. They would suddenly change the topic or stop talking when you walked by. Thankfully, my parents were both pretty well-liked, so that was a rare occurrence.

Oddly enough, when my mom and dad were young, they were both given the opportunity to become professional actors but quickly realized they were not temperamentally suited for it. But, it worked out because they both fell into teaching, and you could tell by their love for what they did that it was the right path for them. My dad directed a lot of the school plays, and I’ll never forget spending time backstage [with him, watching rehearsals and wondering if I would ever be old enough to be in one too. Once I was in high school, I auditioned for every play I could — and was cast in a lot of them — even though my dad always insisted on having a panel do the casting so that it wouldn’t look like nepotism. I was already pretty seasoned by the time I got to Brown.]

When I first started college, I decided to major in Classics because it was my mother’s field, and I admired her so much. But I spent more and more time in the Theater Arts department, and when they made it a major at the start of my junior year, I switched. I think it’s safe to say that was a good decision! I acted in plays, choreographed, and directed. I spent three seasons of summer theater, and then, after graduation, I moved to NYC. I roomed with a friend from Brown who I had directed musicals with. When we first moved there, she declared that she would be a musical director on Broadway, and I said I was going to be an actress. Lo and behold, we both reached our dreams which we still high-five about to this day when we get together.

My original plan was to spend at least five years in regional theater and work my way up from there, but six months into being in New York, I was playing Viola in Shakespeare’s 12th Night, in an off-Broadway showcase, and I was spotted by agents. They started sending me out on commercial auditions. Coming from the theater, I found the concept of acting for a camera to be daunting. But one day, it just clicked — I got it — and I landed a string of Proctor & Gamble commercials right in a row. So then they started sending me out for actual television shows. Things happened quickly. I got an offer for one show, and a chance to screen test for another. I gambled on the screen test, because that show was a sitcom and would shoot in front of a live audience — something I was comfortable with. I got the role. The show was called On Our Own, and was, as it happens, the first pilot directed by James Burrows, who went on to be considered the king of half-hour comedy. The show was a big hit for CBS, but they wanted to move it to LA after the first season and the producer, David Susskind, refused. The show was canceled, which was really disappointing at the time, but I was off and running. I spent a couple of years starring in TV movies-of-week and then jumped into features with Alan Alda’s The Four Seasons.
Authority Magazine

Bess, I’m sure you have had a lot of amazing experiences throughout your career. Can you share with our reader one of your favorite stories?

Look — just the fact that I have been allowed to make a living acting for over 40 years is amazing, don’t you think? I sometimes still pinch myself because it doesn’t feel real. While my life hasn’t always been about acting, I’ve taken time off to raise my children as well, and the experiences that I have been lucky enough to have all felt like such a privilege. From filming all around the globe, riding a killer whale in Jaws 3, shooting aerial battles in antique planes for High Road to China, and working with so many incredibly talented actors — all of these are fabulous memories I will always carry.

Also, when I first started, you were either a TV star or a movie star, not both. But I kept trying to make the jump, and I ended up landing a starring role in the movie The Four Seasons, which was the first film that Alan Alda wrote and directed. What an amazing opportunity! And working with Alan, Carol Burnett, Rita Moreno, Jack Weston, Sandy Dennis, and Len Cariou? Now that’s a privilege.
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It has been said that our mistakes are our greatest teachers. Can you share a story about a mistake that you’ve made in your career and the lesson you learned from it?

When I was around 22 — totally green — and doing publicity for On Our Own, we met other actors from various shows on the network. I was making small talk with one actress and asked her what show she was in. She names the show rolls her eyes, and goes, “yeah, that one. The one nobody likes”. I responded with something along the lines of “yeah, I heard it’s not very good,” and moved on to the next person. So I get home later that night, and my phone is ringing off the hook. I picked it up to hear my agent on the other end of the line yelling at me about how this actress was about ready to jump out of a window because I had told her that everyone thought her show was terrible.

So after that experience, I learned to be careful about telling the truth in Hollywood. No actor wants to be told that they are in a role that is not a good fit for them, or that people do not like a show that they’re in..

You’ve been blessed with success in a career that can be challenging. Do you have any words of advice for people who might want to be a part of the entertainment industry, but are intimated by the prospect of failure?

Only go into this business if you can’t imagine yourself doing anything else and being happy because it will break your heart over and over again. But if you do go into it, plan to fail often, and fail better. Don’t take rejection and failure personally; just because you don’t get a role, doesn’t mean you’re not good at your craft. If you’re really lucky, for every 50 roles you audition for, you’re going to get one. That’s just the nature of what we do.

Every industry seeks to improve itself in one way or another. What changes would you like to see in the entertainment industry moving forward?

I’ve been doing this for a long time. The world has changed a lot, and so has our business. I mean, there were only three networks when I began, and television and features were two separate worlds. That sure has changed! One huge positive change has been the increase in diversity. I’m embarrassed and sad to think of how unaware we were decades ago about how underrepresented people of color were in our industry. I applaud that change. I think that women over 50 — maybe even 40 — are still discriminated against. I’m waiting for that to change but not holding my breath.

One thing I worry about is that a lot of the work process seems to be getting less personal — probably thanks to the pandemic, but also due to the rise in remote work. Directors used to be right there on set with you — directing, coaching. Now they have to spend almost all of their time in the ‘video village’ watching the monitors. Casting is another example — it’s rarely in person these days. I think that’s too bad — there was so much to gain from being in the same room with the director, getting their insights and feedback. I hope the pendulum swings back a little on that front. But you know what? This is out of my hands now. There are new generations leading the charge. I love watching what they are bringing to the table. These days, I’m just along for the ride.

Bess, you have such impressive work. Can you share with us some of the projects you are working on now, and what your plans are for the future?

Thankfully during the pandemic, I was able to keep working and continued my role on Bosch, as well as working on Grey’s Anatomy.

Right before the pandemic hit, I was cast in the pilot season of a new Showtime series called I Love That for You, which ultimately ended up happening, but we had to wait until March of 2021 to start shooting. It’s been a terrific show to work on. I love the whole cast, which is led by Vanessa Bayer, Jenifer Lewis, and Molly Shannon. It’s been a real hit, and we’re all keeping our fingers crossed that it gets picked up for another season.
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If you could inspire a movement that inspires the most amount of good and the most amount of people, what would that be? You never know what your idea can trigger.

You know, as someone who was not on any type of social media until recently, I never knew how much of an impact one person can have, so this is an interesting question to me. I haven’t posted on social media because I tend to be a pretty private person. But it’s been a cool experience to see that things I’ve done in the past continue to have an impact on people. I’m always touched to see someone tag me in a post revolving around a previous film or show that I was a part of and it has made me realize that people do care and remember things you were involved in, no matter how long it’s been. So developing a presence online is a post-pandemic goal.

I’m also a big believer in the mentality of “think globally, act locally.” Because I was raised by schoolteachers, and because I’ve raised two children, education is very important to me. I’ve spent 25 years on school boards, and I love that. Being in the industry as long as I have, I’ve gone from being the baby on set to the woman who now gets called Ms. Armstrong and asked if I need a hand stepping out of the makeup trailer, which is pretty funny, but also pretty humbling. These experiences made me realize that how you treat people is very important. How is the person doing lighting or the sound boom being treated? What about the PA who comes in and asks you what you want for lunch? I try to stay aware of everyone and treat them all as equals because they work very hard for their positions and are usually there before you come in, and after you leave. So I try and use my influence in that sense. I’m a human, just like everyone else. Sometimes I party too much or say something that might be mean, but at the end of the day, we must treat those around us how we would want to be treated.

Thank you for these amazing insights, Bess.

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Yitzi Weiner is a journalist, author, and the founder Authority Magazine. He is also the CEO of Authority Magazine's Thought Leader Incubator, which guides leaders to become prolific content creators. Yitzi is also the author of five books. In 2017, he created the popular, “5 Things I Wish Someone Told Me” series that highlights the empowering lessons learned from the experiences of high-profile entrepreneurs and public figures. This series has inspired a mini-movement among writers, with scores of writers worldwide profiling inspiring people to share their positive, empowering, and actionable stories. A trained Rabbi, Yitzi is also a dynamic educator, teacher and orator. He currently lives in Maryland with his wife and children.

Baltimore, MD

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