It’s not often that I write fan letters. I can remember only one that I’ve ever written, in fact, and it happens that it was written to the person that I’m Zoom-interviewing today, the playwright and screenwriter Susan Sandler.

I wrote to her because when the film director Joan Micklin Silver died in 2020 I was filled with regret that I’d never told her just how much I loved her 1988 rom- com Crossing Delancey, which came out when I was in my mid twenties.

Never before (and rarely after) have I felt so seen by a film, in its story of curly-haired Izzy, played by Amy Irving, caught between her Jewish roots and her aspirations to be part of a glamorous literary world.

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Amy Irving and Peter Riegert in Crossing Delancey

The film’s message — find yourself a real mensch who adores you — was great advice at a crucial turning point in my life. My husband even looks a little like Peter Riegert, who played Sam the humble pickle man who woos Izzy (although my pickle man works in human resources rather than haimisha cucumbers).

Anyway, Micklin Silver is sadly gone, but the film, and the original play were written by Susan Sandler. And her email was easy to find, as she teaches screenwriting at New York University. So I wrote, rather gushingly, to say thank you, and received a lovely reply.

Today’s interview is not meant to be about Crossing Delancey — how can I resist though? — but about her new film, her first documentary and first as a director. It’s a portrait of Julia Scotti, a transwoman and stand-up comedian whom Sandler became friends with during summers on Nantucket island.

“The more I learned about her story, the incredible journey that she’s been on, the heart-breaking separation from her children for 15 years, I realised that there would be this wealth of archival material that would tell the then and now of her story,” she tells me.

The result is searingly honest, funny and heart-breaking, skipping back and forth from Julia now to Rick then, including interviews with the children who struggled to come to terms with their parent’s transition.

Crossing Delancey poster (1988)

Poster for 1988 film Crossing Delancey

The film took six years to make, much of it spent assessing Scotti’s journals and showreels, a job that Sandler savoured. “You know, as a writer, when you’re gathering research, you get pregnant with it, right? You just get so full of it.”

Some of Scotti’s early demo tapes were recorded over home movies, which Sandler would find unexpectedly —“jewels” she calls these clips of family life.

She is grateful to Scotti who was, “absolutely open to everything, she allowed me into every space in her life. From my point of view, it was very much about respecting that trust, by being very protective of her.”

She was careful not to hurt or embarrass her friend. “But she lets us inside, you know, to all of the pain and the doubt, and everything that we all wrestle with privately. As well as the public face, which is very much about giving people joy in her in her comedy.”

SS on set CD pickles

Susan Sandler on the set of Crossing Delancey

It all goes to create a nuanced, warm portrait, which answers many questions about transitioning gender, questions that are increasingly difficult to ask in the midst of a toxic public debate about trans rights. That debate has emerged in the sixyears that Sandler took to make the film, something she finds “shocking”, and she does worry about Scotti’s safety.

But, she adds: “It makes me very happy as an artist to know that the thing that I have made will help people understand what it is to be trans.” Scotti transitioned 22 years ago, when there was far less support available than there is now, but also infinitely less noise and politics about a personal decision.

“There was never a political intention for the making of this film,” says Sandler, “and that has never changed.

"This is a pure portrait, made with great affection and trust. And the simple truth is, this is someone who found her voice. The finding of one’s voice is the essence of everything that’s joyful. It’s what I do in my teaching. I teach at NYU in the film school and helping my students find their voice is what I live for.”

Sandler’s affection and friendship for Scotti is partly because she is Jewish and Scotti is Italian.

“You know, Jewish woman of a certain age, Italian women of a certain age, there’s a kind of bond, you know, an old world bond that we have.

"We talk about that all the time.” Scotti, she says, uses Yiddish beautifully. “ I think you can’t grow up in the comedy world — which is so much about Jewish humour — without getting a little Jewish, you know, along the way. So I think of her as being Jewish too.”

This is my way in to asking about Crossing Delancey, which is Jewish through and through, the New York setting easily translating to anywhere where Jewish grandmothers urge their granddaughters to find themselves a nice husband rather than living “alone in a room like a dog”.

Sandler is touched that it’s “held in a lot of people’s hearts and, being passed generation to generation, which is really sweet.”

It’s a “highly autobiographical” film, she says and she loved writing it and the play that preceded it celebrating her own relationship with her grandmother.

“Parents have intense wishes for their children to succeed in the world. But grandparents just want them to be happy, right? They see through all of that stuff, and they just want happiness, pure happiness, which ultimately is to be loved.”

The delicate ending of the film means you’re not quite certain that Sam and Izzy will find a way to be together, but Sandler reassures me that: “Well, I’m married to my pickle man,” although like mine, he’s not actually in the catering trade. Crossing Delancey was pioneering,
I suggest, in that it’s a film that —decades before #metoo — shows us how young women often struggle to be taken seriously in the workplace amid sexual predators and patronising bosses.

“Yes, the feeling of the way the world worked was not the way I wanted it to work,” she agrees. “All of those pieces, in the struggle of what it is to find who you love, but to also to find your own voice too — so we’re back to that.”

In fiction and, now as a documentary maker, Sandler looks for the same thing: the truth.

“You’re looking for a sense of what is going to move the story forward. Where are the emotional connections? Where are the windows inside a character’s heart? All of those pieces are live in both forms. So that’s what guided me.”

‘Julia Scotti: Funny That Way’ is presented by Bohemia Media on digital platforms March 31. ‘Crossing Delancey’ is available to rent on
Amazon Prime