It's been ten years since I last got to interview Playwright, Lyricist, and Composer Pamela Weiler Grayson. At that time, Pamela's musical (co-written with Alice Jankell) Urban Momfare was playing at the NYC Fringe Festival Encore Series.

Now, Pamela's new play, OBSERVANT, which is the recipient of a 2024 grant from the New York State Council on the Arts and a semifinalist in the Jewish Plays Project’s 12th National Jewish Playwriting Contest, will be headlining the Emerging Artists Theatre’s Bi-annual Spark Theatre Festival NYC.

In this interview, Pamela once again answered my call, but this time around, she reveals:

• How she has grown as a playwright over the past 10 years
• What she hopes audiences come away with after seeing OBSERVANT
• Why it's so important to have this play on stage right now
• Her favorite Jewish traditions
• So much more

Connect with Pamela: Website, Instagram

OBSERVANT will play at the Chain Theatre in NYC from September 12-28, 2024!

In OBSERVANT, three generations of women confront their relationships to their Jewish identities—and to each other. Comedy and tragedy entwine, like a braided challah, when a mass shooting in their community tests the bonds of faith and family. 

1. I can't believe it's been a decade since we did an interview together! The last time we spoke, your play Urban Momfare (co-written with Alice Jankell), was playing the NYC Fringe Festival. Since that time, how do you feel your playwriting skills or the stories you want to tell have changed? It’s crazy that 2024 is the 10th anniversary of URBAN MOMFARE! It’s like my “baby" is 10 years old and I’m thinking, how could I be the “mother” of a show that’s 10 years old?!  I have something interesting planned to mark the 10th anniversary, which I’ll just leave as a little teaser here…

I think I’ve really matured as a writer over the past decade. I have written many plays and one full musical (with co-writers) in that time period, with multiple readings and some awards for a bunch of them.

Continuing to take classes and workshops, and participating in writing labs, has probably been the most helpful in terms of honing my craft and growing artistically. Being in the room (which since Covid is often virtual), with other writers, and leaders in the industry, getting feedback, watching other writers’ shows develop, and having that “safe space” community of colleagues is invaluable.

I’ve been in Kate Moira Ryan’s Writing Workshop for so many years, with a lot of the same writers, that we’re practically a cult. Since 2021, I and my co-writers have also been members of Theatre Now New York’s International Musical Writers Lab, which meets every other Sunday afternoon on Zoom. These workshops and labs keep me sharp and fresh, and I’ve learned so much from them, especially about storytelling and structure.

I’ve been writing more plays than musicals since 2014, as they are easier to write alone and to get produced. While my first love is still musicals, I have grown to love writing plays as well. The stories I’m telling now are still ones that excite me and are usually inspired by deep questions I have about relationships, especially through a female lens. I’m tackling some tougher subjects these days, although I still believe in the power of comedy, and it’s hard for me to write a play about a serious topic, without sprinkling in a good amount of my dark humor.

2. This September, your latest play, OBSERVANT, will be playing at the Chain Theatre, headlining the Emerging Artists Theatre’s Bi-annual Spark Theatre Festival NYC. What does it mean to you to have your play as the headliner? Having OBSERVANT as the headliner in EAT's Spark Theatre Festival is incredibly meaningful to me, and I’m thrilled to have this opportunity for a full production! As you know, URBAN MOMFARE started out at EAT many years ago, when we first began developing it, and they helped us get produced for the Fringe in 2014, so having a new play that’s part of EAT’s festival, is very special. Paul Adams, EAT’s incredible artistic director, has been a huge supporter of me and my work for the past 10 years, and I’m so grateful. I’ve supported the theatre as well all these years, and it’s basically a mutual artistic and personal love fest. We put the “fest” in festival!!

3. Let's go back to the beginning. What event, thought, or conversation sparked the idea for you to write OBSERVANT? I’ve been contemplating writing a “Jewish” play for some time. I grew up Reform, in Manhattan. While I went to Sunday School at Temple Emanu-El, my family really celebrated Christmas (not in a religious way, but we did all the other stuff). I didn’t have a lot of Jewish friends, as there weren’t many in my school at that time. But during college, I wound up connecting with more Jewish people, and in law school my best friend happened to be Modern Orthodox.

Many times, when she took days off, I was like, “What holiday is this again?” I met other people along the way who were more observant, and I became very conscious of the fact that observant and non-observant Jews were sometimes quite judgmental towards each other - at times it felt like we weren’t even alike at all. I thought it would be interesting to write a play about this dynamic, especially if it occurred within one family.

The actual incident that inspired me to sit down and start writing my “Jewish play” was the Tree of Life shooting, in 2018. That temple shooting in Pittsburgh was a watershed moment for Jews in this country, and that’s when many of us began to feel the weight of our Jewishness in ways we never had before. I realized then that I wanted to write about how violent acts of antisemitism affect Jewish identity, because suddenly, we all had to think about it.

Cast of OBSERVANT
(Top Row: left to right) Yair Ben-Dor, Arielle Flax, Rebecca Hoodwin
(Bottom Row: left to right) Arielle Beth Klein, Melissa Wolff, Fady Demian

4. What do you hope audiences come away with after seeing OBSERVANT? I hope that audiences are able to reflect on how important it is to strengthen our sense of community and heal our internal conflicts in order to survive and combat the violent hate and toxic polarity that seems to be exponentially growing in this country and around the world.

I’d also like audiences to come away with a greater understanding of the complexities and diversity of Jewishness, and how we become forced to re-examine our identities when faced with serious existential threats.

Finally, I want audience members to let themselves laugh, because humor is the way Jews have coped with trauma for thousands of years, and that is probably one thing that’s never going to change – at least I hope it never will!

5. According to press notes, OBSERVANT is about three generations of women who confront their relationships to their Jewish identities—and to each other. What are some Jewish traditions you knew, growing up, you would always keep? Which ones came into question as an adult? While we were not that big on Jewish traditions in my family, I always loved the Passover Seder. I mean it has it all: singing, stories, and food. And you don’t have to fast, which is definitely a plus. Actually, we didn’t fast at all when we were kids, and now I don’t because I have acid reflux, which might be the most Jewish thing about me.

I still love Seders, and for many years we did them at our apartment. It was great watching my kids enjoy that holiday, like I did. I also really loved lighting the Hanukkah candles, and singing the blessings over the Menorah, with my dad. Of course it was also nice to get Hanukkah gifts, but we didn’t get that many because we also got Christmas presents, as long as we left cookies and a glass of scotch out for Santa (yep, it was the 70’s and “Santa” drank scotch).

I loved lighting the Hanukkah candles with my own kids, and even though they’re grown, I still light the Winnie the Pooh Menorah that we got when they were little. Pooh wears a yarmulke, and I just love that so much! I can’t think of any traditions that came into question as an adult, because I was just happy to hang onto the few that I had.

6. What was the hardest scene for you to write in OBSERVANT, and why do you feel this scene was so difficult? I don’t want to give away any real details about the scenes in the play, but I will say that it was particularly challenging to write about one of the characters who describes her experience as a survivor of a mass temple shooting. I had to research it and also get inside the head of someone who experienced that, finding the right tone and mix of emotions. I’m probably most proud of that scene. But I also had to work really hard to figure out how to end this play, as there's no easy way to wrap up a play about such a traumatic incident, especially with six characters who each have their own emotional arcs.

7. The show also deals with how to come to terms with and try to improve a violent & chaotic world, when we can't even seem to get along with our own families, communities or reconcile our internal conflicts. With all the chaos and violence happening in today's world, what would be some of your suggestions on how to make this world more peaceful? What are some internal conflicts you have experienced or are going through that you'd like to resolve that you feel would make life easier to live? After delving into all this mishegas, I think that a lot of the healing we need to do in this world first has to start from within. Once we wrestle with our personal issues and try to be more accepting of our own identities and flaws, while striving to improve and grow, we can then move outward to do the same thing with our families, then with our communities, and hopefully then on a more national and global level.

We definitely need to build more bridges, and I’d love to see more dialogue between people, both intra-faith and inter-faith. The intra-faith piece is important, because when Jews fight amongst ourselves, as we are seeing right now in this political climate, it makes it harder to be strong against antisemitism. I have had these struggles personally with my Judaism, and I want to do better. I also have struggles with anxiety, which is also probably one of the most Jewish things about me and related to my reflux (see above), so I think if I could manage that better, it would make life easier, both for me and my family. Although maybe not for the makers of Tums and Pepto Bismol.

Pamela Weiler Grayson's Winnie The Pooh Menorah

8. OBSERVANT was the recipient of a 2024 grant from the New York State Council on the Arts and a semifinalist in the Jewish Plays Project’s 12th National Jewish Playwriting Contest. For those of us who don't know a lot about the playwriting process, how did this grant help you bring OBSERVANT to life? The grant from NYSCA was really the catalyst for the production of this play. I was incredibly lucky to get that grant, as I know it’s not easy to get grants, and one of the requirements of the grant is to use that money in that calendar year. So, I knew that I had to use the money in 2024.

Because I had already done prior readings of the piece, including a staged reading in fall 2023, the next step was a production, so this was the perfect way to use that grant. The NYSCA funding will help defray some of the costs of actor and creative team fees, even though there are still many more costs associated with the production. It’s a huge help! And I’m also getting a lot of financial support from Emerging Artists Theatre, as part of the festival, particularly with theatre space.

9. Where is your favorite place to write, when you are writing a play? I always say that when writing songs, I do my best work in the shower (nothing like the acoustics and the privacy!), but for plays, I guess I have to give you the boring answer of sitting at my desk in my library/study (which is my “home office’). I love my writing space, as it’s painted in this fabulous dark green color, which everyone on Zoom always talks about, and it’s my sanctuary. I can write elsewhere, but I need quiet.

I’m not one of those people who can write scenes on my laptop at Starbucks, while the people next to me are bitching about their boyfriends. I do often think about my plays while I’m taking walks, or sometimes while I’m getting a pedicure. In those cases, I’ll take some notes on my phone, which I’ll later either transfer to my laptop or delete because I’ll decide they are complete trash and not usable.

10. How do you keep your focus when writing a play? For example, do you lock yourself in a room and put up a sign that says "Do Not Disturb"? or Do you turn off all your phone notifications until you finish writing for the day? I don’t just sit down and write for hours, usually. I’m not that disciplined and I need breaks. And I need to be inspired. I love writing in my green library/study, and usually I’m alone during the day, so it’s not hard to have privacy. I should turn off notifications, but normally I don’t. A lot of times I’ll admit I use those notifications as an excuse to take a break and check emails and texts. And social media can be a rabbit hole as well, so I try not to check it too often. But I don’t have the best will power, and I’m about to check Facebook right now before I answer the next question, so yeah, I’m probably not going to teach a course in writers’ time management.

11. What is something we didn't get to talk about in this interview that you'd like my audience to know about you? I feel like I've told you only a little bit less about me than I’ve been telling my therapist for the past 20 years, so I can’t think of that much more. Seriously, though, I do want to say that I started my career as a playwright and musical theatre lyricist/composer quite late. I had multiple careers before that, including being a performer, a stint as a lawyer, and many years as a freelance writer, plus mothering two kids.

The day I turned 50 I found out that URBAN MOMFARE had been accepted into the NY Fringe. And the year I turned 60, which was this year (yes, I’m trying to combat ageism here!), I found out that OBSERVANT was going to have a full production and was the recipient of a grant. I am passionate about “older” writers being given opportunities, especially older women, so the fact that I’ve been able to share my work and have it recognized, in mid-life, is really important to me. I’m also passionate about chocolate, which is another reason why I have reflux. See you at the theatre!

Pamela Weiler Grayson

More on Pamela Weiler Grayson:

Pamela Weiler Grayson is an award-winning plays and musicals have been seen on stages throughout the country, including Primary Stages, The Group Rep/Lonny Chapman Theatre, Cincinnati Lab Theatre, and Emerging Artists Theatre. Urban Momfare (composer/lyricist/co-book writer) won a Best Musical award at the New York International Fringe Festival, garnered four stars and a Critics Pick from Time Out. The Sustain, co-written with Alice Jankell and composer Aaron Drescher, and developed in Theatre Now New York’s International Musical Writers Lab, was a semifinalist at the 2021 Eugene O’Neill Theater Center’s National Music Theater Conference. OBSERVANT is the recipient of a 2024 grant from the New York State Council on the Arts and a semifinalist in the Jewish Plays Project’s 12th National Jewish Playwriting Contest. Dramatists Guild member. Education: Brown University, Fordham Law School, New York Theatre Workshop, and The BMI Musical Theatre Workshop.