Interview: Holly Sidell on Portraying Isabel in CROSSING DELANCEY

The romantic comedy Crossing Delancey, written by Susan Sandler, premiered off-Broadway at the Jewish Repertory Theatre on April 25, 1985. In 1988, Warner Bros. released a film adaptation of the play starring Amy Irving as Isabel, or Izzy, a modern young woman who lives alone and works in a New York City book shop. When she is not pining after Tyler Moss, a handsome author she admires who frequently drops by to check on sales of his latest book, she is visiting her grandmother (Bubbie) in Manhattan’s Lower East Side who knows what Izzy needs to be really happy is to be married to a nice Jewish man with whom Izzy can start her own family.

Isabel is shocked to find out Bubbie secretly hired Hannah the Matchmaker to find a good Jewish man for her to marry. (L-R) Sharron Shayne, Holly Sidell, Amy Tolsky

So, the irascible granny and her friend, Hannah the Matchmaker, have conspired and found a “good catch” for Isabel, whose initial reluctance gives way to a blossoming romance when she finally meets Sam, the pickle vendor. But will she give up her pursuit of the aloof author and realize Sam may be the right man for her? After all, the desire to love and be loved in return is universal, but so is the desire of parents for their children find happiness in ways they approve.

Told through a series of vignettes, Crossing Delancey examines the old-world Jewish family custom of all young women needing to find a husband as soon as possible to settle down and raise a family against a modern 1980s Jewish woman in New York City learning to stand on her own two feet. Sandler’s charming tales offers wisdom on both sides of the equation, ending with the more traditional outcome but acknowledging that modern women can have it both ways – as long as they find a right man as their life partner.

I spoke with Holly Sidell (pictured) who is portraying Isabel in the current production of Crossing Delancey at Theatre 40 in Beverly Hills through June 21. Here’s what she had to say about her interpretation of the character, her desire to take on such a demanding role, and why she feels the characters speaks to the struggle of young Jewish women everywhere who struggle to find the balance between pleasing your family and yourself at the same time.

Hi Holly. First of all, Crossing Delancey is deeply rooted in Jewish tradition and the immigrant experience. Were you raised on the Lower East Side or have relatives who live or lived there to offer you inside information about what life there was like?

I was born and raised in Los Angeles, but my dad grew up in Rogers Park, Chicago, an area heavily populated with Jewish immigrants from Eastern Europe, much like the Lower East Side in New York. My dad’s grandparents were immigrants, and although my dad does have some stories, my grandfather died before I was born and my own Bubbie passed away when I was very little, so I never really got to know her in that way or hear more stories firsthand. But still, there’s something about the culture and importance of/emphasis on tradition in Crossing Delancey that feels connected to my roots.

Also, through a past relationship, I spent many years around a close-knit family whose path was very much like Bubbie’s, originally from Eastern Europe, settling on the Lower East Side (although they eventually came to Los Angeles). The way they shared stories, memories, and family histories, and the way they talked to and related to each other, reminds me so much of the world of the play, especially the matriarch of that family. Spending time around them gave me real insight into that world, and was very special to me.

New world values clash with old world tradition each time Isabel (Holly Sidell) and her Bubbie (Sharron Shayne) get together.

You call Isabel a “bucket-list role” for you. What has drawn you to play her?

First, as an actor, it’s a gift to get to go on a complete character journey and transformation like Izzy does, and those opportunities don’t come along every day. But beyond that, there is something deeply personal to me about getting to inhabit this world. As mentioned above, my dad’s grandparents were immigrants, but I never really got to fully know that part of my family history. So there’s something special about stepping into a play like this and imagining or experiencing what life may have been like for them.

I also think it’s important to make sure stories like this are continued to be shared, and that tradition and Jewish lineage preserved. There’s a line in the play where Sam says that the older generation tells stories, and that “they’ve got to talk about it to make it real.” I love that line, because I think that’s part of why this play still resonates. As older generations pass on and life changes so quickly, there’s something ceremonial (and crucial) about holding onto, and acknowledging, these memories. To honor the generations that came before us - their lives, sacrifices, and everything they endured.

The cast of Crossing Delancey at Theatre 40.
(L-R) Amy Tolsky, Ari Hagler, Holly Sidell, Matt Landig, Sharron Shayne. 

How did you first get involved with the Theatre 40 production?

Theatre 40 does a series of weekly play readings throughout the year, where members come in and read the roles. We did one of Crossing Delancey in early 2025, and I got to read Izzy (and Amy Tolsky read Hannah!). As mentioned above, Izzy has been a bucket-list role for me, and the reading made me fall even more in love with the play and Izzy. So when it was then added to the upcoming season, I was hoping it would work out that I’d get to play her – and thankfully I got cast!

Is this the first time you have worked with director Jonathan Fahn as a director? If not, on what else and where?

Jonathan actually directed my one-person show, Deconstructing Holly, which premiered literally the day before the world shut down from Covid. We worked very closely together on it for several months, and then again later for a run at the Hollywood Fringe Festival. Because the piece was autobiographical and extremely personal, I knew I needed a director I felt truly safe with, someone collaborative who could bring an outside eye to material that was so deeply personal to me, create a safe environment to explore difficult material, and help shape the piece alongside me.

This is the first time we’ve worked on a full-cast production, and it’s been wonderful coming back together. As an actor, your relationship with your director is everything, because sometimes you’re too inside the work to fully see what you’re doing. You need someone who can guide you honestly while also creating an environment where you feel comfortable trying things, asking questions, and exploring. Jonathan creates that kind of space, and I think he’s done a beautiful job with this play.

Isabel (Holly Sidell) has a crush on Tyler Moss (Matt Landig), a writer whose books she sells in the bookstore where she works.

Now let’s talk about Isabel’s internal tug-of-war between her upwardly mobile, independent uptown life and her traditional, deeply rooted Lower East Side family heritage. How do you identify with her, both her search for love and wanting to pursue her own career?

I think Izzy tells herself she’s happy being single because she’s afraid she can’t have both love and independence. For her, it’s not just about romance; it’s also about what stepping back into that world of tradition and expectation might mean for her identity. She’s worked very hard to build this sophisticated, independent life for herself, and part of her fears that embracing the life Bubbie wants for her means losing a part of herself. She even says, “I have the luxury of going anywhere I want to go… doing anything I want to do,” and yet she doesn’t do those things. She has built an independent life, but hasn’t quite given herself permission to fully live inside it.

It’s also very interesting that she says, “I don’t have any ambition,” because I don’t believe that’s true; I just believe she isn’t allowing herself, or fully knows how, to claim that part of herself yet. Tyler represents this very intellectual, artistic world that she aspires to be part of, so I understand why she’s drawn to him – and I have this little personal vision that after the play ends, Sam becomes the person who encourages Izzy to actually explore her creative side.

And by the end of the play, Izzy isn’t really becoming someone else — she’s reconnecting with parts of herself she had shut down. One of my favorite moments is in the final scene, when she toasts with Sam and says “L’chaim.” It’s the only time she speaks Hebrew in the play. It’s such a small moment, but to me it signifies opening herself back up to that part of who she is, ending the tug of war, so to speak.

Isabel is shocked to find out Bubbie secretly hired Hannah the Matchmaker to find a good Jewish man for her to marry.
(L-R) Sharron Shayne, Holly Sidell, Amy Tolsky

Do you view Izzy’s initial resistance to the matchmaker (Hannah) as an act of personal empowerment, or as a defense mechanism against living within her family’s old-world ways? 

I think it’s both. On one hand, Izzy is fighting for her independence and trying to define herself outside of what everyone expects from her. But also part of her resistance is defensive. She’s so determined to separate herself from that world that she initially dismisses the wisdom within it.

The pressure around marriage and family, while frustrating to a modern woman like Izzy, comes from a very real desire to keep people connected and preserve a sense of lineage and continuity. And she begins to recognize that there’s wisdom in some of what Bubbie and Hannah want for her - she just has to find her own version of it.

Isabel is less than impressed when Hannah the Matchmaker brings Sam the Pickle Man over to meet her.
(L-R) Amy Tolsky, Ari Hagler, Sharron Shayne, Holly Sidell

The audience watches Izzy slowly recognize the depth of Sam (the "Pickle Man") as he has private conversations about her and life with Bubbie. I have always thought Izzy was eavesdropping on them without being seen by the audience, and hearing him changes her mind about his potential as a husband, especially since she seems to change her attitude about Sam soon thereafter. Are you, in fact, listening to the scene backstage?

I love that idea. That actually isn’t how I’ve been playing it, no, but you’re right that when Izzy hears from Bubbie that Sam came over to wash her windows (in the scene you’re referring to) it is a turning point. Izzy loves Bubbie fiercely. Even though she struggles with the traditions, the pressure, and separating herself from that part of who she is, Bubbie is still her heart. So hearing that Sam came over to help take care of Bubbie is when she starts opening to him on that level.

Do you think realizing it was Sam who sent her the hat influences how she feels about him?

Holly Sidell models Isabel's new hat. Photo courtesy of Holly Sidell.

Yes, in a few ways. First, Izzy is a fantastical romantic (as the audience gets glimpses of when she breaks the fourth wall and shares her inner thoughts), and the idea of being wooed is exciting to her. Second, she loves the hat. It makes her feel cool, sophisticated, freer somehow. And the fact that this man who she thinks is not sophisticated or up to her level or standards picked it out completely throws her. Sam sees a side of her she doesn’t think he’s supposed to understand. The hat brings something out in her, and the image she has of him starts to crack a little.

What do you see as the exact moment or line where she realizes Sam is actually her equal rather than just a "schlub"?

The hat definitely starts opening that door, but the exact moment is when she learns that Sam took writing classes from Tyler Moss, this man she has put on such a pedestal, and that Tyler thought Sam’s work was good enough to be published. Up until then, Izzy has been viewing Sam through a very limited lens. Suddenly, she realizes he exists in the intellectual and artistic world she values too, completely destabilizing the assumptions she’s made about him.

The awkward silence between Sam the Pickle Man (Ari Hagler) and Isabel (Holly Sidell) speaks volumes.

Ari Hagler portrays Sam in the Theatre 40 production. Have the two of you worked together before as actors? And if not, how do you approach the heavy romantic tension and mutual teasing in your scenes with him? Was there an intimacy coordinator on the production?

We had never met until callbacks, but as soon as we started the scene together, I immediately thought, “Wow… he is Sam.” Ari is a very grounded and present scene partner, which made the chemistry between Sam and Izzy much easier, and more natural, to build. As actors, we create these relationships very quickly, so trust and communication become a huge part of the work, along with making sure there’s safety underneath everything. Because that foundation exists between us, we’re able to really live in the moment as Sam and Izzy, rather than trying to manufacture attraction or tension. A lot of it simply comes from each of us doing our own work honestly and responding to where the characters are with each other in each scene.

Ari and I talked about it together, then with Jonathan, and ultimately felt we didn’t need an intimacy coordinator for this production. And sure, the first stage kiss with anyone is always a little awkward, but after that it becomes almost like choreography. Once that structure is in place, it gives you the freedom and space to really live truthfully in the moment.

Sam the Pickle Man (Ari Hagler) returns for a second time to take Isabel (Holly Sidell) on a real date. But is she ready to go out with him?

How about the other actors, Sharron Shayne as Bubbie, Amy Tolsky as Hannah, and Matt Landig as Tyler. Have you worked with any of them before? Where and in what play?

I had never worked with Sharron before but have been a fan of her work from afar for years, and am so happy to get to share the stage now. Amy and I had only ever done the Crossing Delancey reading before – and I couldn’t imagine anyone else as Hannah. So I feel very lucky we’ve gotten to do this together! The first time I worked with Matt was many, many years ago in a production of Moon Over Buffalo in the Palisades. We’ve done a few readings together since then, but this is our first full production together at Theatre 40, and it’s a true pleasure to work with him; the Tyler scenes are so fun. Honestly, everyone brings so much to these characters and is so good at their craft, and I feel very lucky to get to tell this story with them.

Bubbie (Sharron Shayne at center), shares her old world knowledge about dating and marriage with Sam (Ari Hagler) and Isabel (Holly Sidell).

Since the close-knit Bubbie and granddaughter relationship is so essential to the production, how did you and Sharron Shayne evolve into making the characters believable?

Sharron makes it easy. We’ve spent time together outside of rehearsal and shared vulnerable stories and parts of our lives with each other - especially stories about her childhood, her family, and growing up in the same kind of world as Bubbie, which has added so much richness and specificity to the relationship for me. I also genuinely love her as a person, so getting to inhabit this grandmother-granddaughter relationship with her has been special. What’s beautiful about Izzy and Bubbie is that they can drive each other completely crazy, but the love underneath it is never in question, and I’d like to think Sharron and I have created our own version of that in real life.

Tyler (Matt Landig) meets Isabel (Holly Sidell) for a drink. But she is disappointed he is not interested in her romantically.

Why do you think Izzy decides Tyler is not the right man for her after wanting to get closer for him for so long?

As with so many things in life, the reality rarely lives up to the fantasy. And while that realization can be painful, it can also be freeing. Izzy goes through a process I think many women experience in real life: longing for the exciting, unavailable man, only to realize that the true love story is ultimately with the stable, consistent person who makes you feel truly seen, safe, and cherished.

Is there anything else you would like to add about yourself and/or the production?

Someone described our production as feeling like a warm hug and a gentle smile, and I love that because we really do hope that’s how people leave feeling. Yes, it’s funny and romantic and nostalgic, but underneath all of that, I think the play speaks to something very universal. No matter your background, culture, or traditions, we all ultimately want the same things — connection, belonging, to love and be loved, and for the people we care about to be happy.

Thanks so much, Holly, for your insights on the Crossing Delancey characters and story.

Crossing Delancey, a romantic comedy written by Susan Sandler is directed by Jonathan Fahn and produced for Theatre 40 by David Hunt Stafford. Performances continue in the Mary Levin Cutler Theatre, 241 S. Moreno Dr., Beverly Hills, CA 90212 through June 21 on Thursday through Saturday at 7:30 p.m. and Sunday at 2:00 p.m. Theatre 40 is located on the campus of Beverly Hills High School, with ample free parking in the designated lot after entering via a driveway at the intersection of Durant and Moreno Drives. General admission tickets are $35 with reservations by calling (310) 364-0535 or online at http://theatre40.org Available seats are sold at the door a half hour prior to show time.

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