ESTHER POVITSKY has forged an extremely prolific career in comedy, with standup success (her Adam Sandler-produced Comedy Central special Hot for My Name premiered in 2020), multiple podcasts (My Pleasure and Trash Tuesday among them), her own TV series (Freeform’s Alone Together, which she co-created and starred in), and roles in other shows such as Crazy Ex-Girlfriend and Dollface and films including Home Sweet Home Alone and Mark, Mary & Some Other People. But if touring, acting, podcasting, and TV writing weren’t enough, Povitsky has now co-written a feature comedy in which she takes the lead as an actor and executive producer.
DRUGSTORE JUNE stars Povitsky as the title character, a wannabe influencer who finds a new calling as an amateur sleuth when the small-town pharmacy where she works is robbed. Co-written and directed by Povitsky’s frequent collaborator Nicholaus Goossen, Drugstore June boasts an impressive supporting cast featuring acting veterans James Remar, Haley Joel Osment, and Beverly D’Angelo, and comedy pros like Bobby Lee, Matt Walsh, Ms. Pat, Al Madrigal, and Bill Burr (the latter two also executive produced the film).
Utopia and Shout! Studios will release Drugstore June in Los Angeles and New York theaters on February 23, and in additional cities on March 1. We spoke with actor/screenwriter/executive producer Esther Povitsky about how her newest creative endeavor came about.
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COLIN McCORMACK: When you were growing up early in your career, did the performing and the writing always go hand-in-hand for you? Did writing for yourself come about later?
ESTHER POVITSKY: That’s a good question. I would say it came about later accidentally. As a standup comedian, I think my brain was not fully developed yet. I didn’t realize I was already a writer-performer, I didn’t put it together. That’s how I realized, Oh, maybe I should also try to write my own TV or film projects. But certainly, the way I got into all this was much more superficial and came from wanting attention. My foot in the door was just wanting to be seen and looked at and be a pretty actress, and then the rest of it came about on its own by accident. I’m not proud to admit that, but it is the truth.
CM: I think it’s probably the truth for a lot more people than would admit. How did the initial idea for Drugstore June come about?
EP: Originally, my writing partner [and] director, Nick Goossen, and I had written this as a web series for ABC Digital, which is now defunct, as is the concept of a web series. I don’t think those exist as much anymore, but they had a moment where that was going to be the next big thing. A lot of companies were putting money into that, so we were hired to write this series for ABC Digital and then they went out of business. And we [thought], Wait, we love what we wrote and they don’t have any use for it, so it’s ours. At the time, my TV series Alone Together had just gotten picked up so we [couldn’t] turn this into a show because I can’t do another show. And Nick, who has had lots of experience in the feature world, said, “Let’s write a movie.” I have no faith in myself in learning new things. I was like, “I can’t write a movie. I don’t know how to write a movie. That sounds like the hardest thing in the world.” He was like, “No, I’ll show you the structure.”
He took that upon himself and helped figure out the story structure of turning something into a feature. And then my thing was the character and the humor. Peppering in all the very Esther-y details, making sure those were perfect, and obviously helping with the story. We wrote the movie and a lot of it was based on my early-twenties messed up era. I was just a girl with no hobbies, no interests, really self-absorbed, obsessed with her ex-boyfriend, live-streaming every boring detail of her life every day. It’s very much, unfortunately, true to life.
CM: Speaking of Nick, he also directed your Comedy Central special. How did you two first end up meeting and connecting?
EP: He was a really big fan of the LA comedy world. At the time — maybe this was 10 or 15 years ago — I had a podcast with the comedian Brody Stevens, the Brode & Esther podcast. And [Nick] was a big Brody fan, so he had seen me on that and then reached out and was like, “I’d love to work with you.” We met up for burgers and had similar sensibilities, which almost makes no sense because he’s this super tall, masculine guy who comes from a boxing dynasty family. He’s really tough but then also has a very Esther-y personality on the inside, he just loves desserts and being self-deprecating. So we found that we had a very similar sensibility and stayed in touch. Our professional relationship started there and he would call me in to audition for certain projects he was working on and he cast me in a couple of his web series. Then together we sold that [web series version of Drugstore June] and that was our first thing. And then from there, we made the special together and now the movie.
And oh my God, I’m telling you, you really want a tall, confident white guy on your team because the place where we are so opposite is he’s like, “We’re gonna do this. We’re gonna sell this. We’re gonna get this made.” And I’m like, “There’s no way. You are delusional. You are crazy.” And then it happens. I have all the insecurities, so we are a good pair in that way where he has so much belief and faith. I’m trying to learn from that. It’s hard not to since he’s been able to pull so much off. With the special, he called me and said, “I showed Adam Sandler your standup and he wants to produce your special, so we’re going to do a special.” And I was like, “What? I can’t do a special!” I was crying, “I’m not ready. I can’t do it.” So it’s been really helpful for someone like me to have someone like him on my team just being like, “No, you can do this.”
CM: What was the moment where you finally realized, “Oh, Drugstore June is happening, we’re doing this”?
EP: They kept saying it’s happening and I was like, I’ll believe it when I see it. All the pre-production, I was still not believing it. But once we started shooting it, I was like, Okay, I guess we’re at least going to shoot this movie. You hear these things about indies that never see the light of day, they never come out, so I had been really scared about that. In my TV career, I have had the experience of writing a pilot and it doesn’t go anywhere. These are things you’re so attached to emotionally and you probably shouldn’t be, you should just look at it as a job. But I feel very connected to my work and it’s so important to me and I probably take it too seriously sometimes. And then not seriously enough in other ways, of course. In TV, once your show gets picked up, it seems like the network spent a lot of money and they’re going to put it out. But in movies, I just had no experience to know. So I still feel, Oh my God, people are going to see this movie. I’m just happy people saw the trailer. That’s huge. Every little thing for me is huge.
CM: As an actor, do you approach a role that you wrote for yourself differently than when you’re acting in somebody else’s script?
EP: Yes, totally. Because if I wrote it, I almost don’t even need to think about the performance. I know inherently what I’m going for. I’m biased, but I think the writer is the most important person in the process. So when I’m not the writer, it’s so unbelievably important to me that I am carrying out what the writer wants and more importantly, that I feel like I can and I’m capable. I’ll get sent an audition and I’ll read it and I’ll be like, I can’t do what they’re looking for. This is not for me. And then on the flip side, when an audition like Dollface came in, I’ll never forget reading that script and being like, I know that I got this, I can do this. Maybe I’m not what they’re looking for, but I know I can show them something that is on the page. I always look for that really strong connection. Otherwise, I don’t want to waste people’s time. I’m not Daniel Day-Lewis, I am a standup comedian who does podcasting. I know my strengths. Maybe one day I will be able to work with someone to step outside those current strengths. I like to be super self-aware of what I can pull off and what I can’t. I recently met with a director on a project and I was like, “Look, I don’t know if I can do this. There’s a chance and I want to figure it out with you. But I don’t know.”
CM: That’s where your trust in a director, and vice versa, really comes into play.
EP: Yeah, it’s got to be there.
CM: You and Nick wrote the role of June for yourself. With the other roles that fellow comedians are in, were you writing those with specific actors in mind?
EP: The role that Bobby Lee played, we always knew he should be my boss. He was someone in our universe that we loved and wanted to work with, so that was one we specifically based on him. My brother, played by Brandon Wardell, we had him in mind right from the get-go. And then a lot of them it was not like that. We didn’t give thought to the smaller parts until we got to casting. Then it was still so easy and fun to be like, “Oh my God, of course Trevor Wallace should be this and Jon Gabrus should be this and Nick Rutherford that.” So it was really easy and fun to plug those people in and watch them fully flourish, Steph Tolev, Brittany Furlan, Ms. Pat. When you get a comedian to set and you know how to give them the right role for who they are, you just watch them go for it. I’ll never forget Ms. Pat walking into the scene the first time and just improvising, looking at me and being like, “Look what crawled out of a rat’s ass.” And I just was like, Who would say that? That’s so funny. It’s so mean. It’s so original. I always say I’m a fan of comedy way more than I am a comedian. Getting to watch those people do their thing was the most fun.
CM: Once you were on set as a performer, did you ever have to put the writing hat back on to make any changes or adjustments on the fly?
EP: There were a couple of moments where we were like, Oh, I think we made a big mistake. We had to fix a few things. Luckily, from TV experience, I see that happen all the time and it always tends to work out. I will say this, because I never took the movie seriously because I have no self-confidence, up until we started shooting I had all the real names of people in the movie, including my high school ex-boyfriend. So we literally got to set and I said, “I think we should change the names.” And we had to do it in such a split second that I just gave him, without thinking, a version of my fiancé’s name, Dave. We’ll call him Davey because it’s not quite Dave and it sounds a little bit like the original name. That was something where I was like, “We should change this right now. This is our last chance.”
CM: I’m sure the distributors’ lawyers are very happy that you realized that.
EP: [Laughs] Yeah.
CM: As a standup, you obviously get immediate feedback on your jokes as they land. How was that with the script and the final cut of the movie? Did you guys do a table read to see how everything went? Were you part of test screenings to see how the final result went?
EP: We did a table read, which was so much fun and we got good feedback through that. Mostly, the experience of the table read was, Oh my God, these performers are so funny. We made all the right casting choices. We’ve had a couple of screenings, but I would say that we have a really good team between our director, our producers, myself, and my fiancé Dave King (he’s a writer/producer and he weighed in a lot). Nick had a couple director friends weigh in. Adam Sandler was really involved in a screening and giving notes. Within our little comedy community, we took a lot of notes and figured it out before testing it on an audience. Which is different from standup, you’re totally right. Standup is so weird in that the audience is, I don’t want to say all that matters because you have to find it funny first, but at least with standup if you find it funny and it’s bombing, you’re not going to keep doing it unless you’re crazy. Which sometimes I do, but I shouldn’t.
CM: You’ve done so much in different avenues within the industry. Is there still something that you haven’t delved into yet that you’ve been wanting to try?
EP: That’s a good question. I think I just want to do more of what I’m doing. That’s always been my answer in this arena. I’m always open to other things that feel like they ring true and get a yes to all the questions of: Is this funny? Is this honest? Is this true for me? I don’t know what that could be. Obviously, I want to be in a Broadway chorus, that’s what I really want to do even though I’m 35 and five feet tall. I’m still holding onto hope that that could happen. I’m eight months pregnant right now, so after the baby, I am looking forward to doing another standup tour and standup special. I feel eager about getting that done and then seeing where I feel on the TV and film front. A lot is about to change for me with having a baby, so I’m excited to let that change me and see where that takes me creatively.
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Thanks to Esther for talking to us about DRUGSTORE JUNE. Learn more about the film at drugstorejune.com.
This interview has been edited for length.
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