The ambitious ‘Leopoldstadt’ finally arrives in Chicago area

It’s easy to think British playwright Tom Stoppard lived a charmed life. He was the toast of the West End, and his writing garnered some of theater’s most prestigious awards, from the Oliviers to the Tonys to an Oscar.

Even Stoppard said his life was charmed, until he began wrestling late in life with a reckoning — numerous family members had been killed in Holocaust, and his Jewish identity was something he hadn’t yet tried to understand.

This scrutiny of his own history fueled his final play, “Leopoldstadt,” a Herculean undertaking for any theater company with its original cast of 38, five acts and five decades of familial history. Before his death in 2025, Stoppard mined his own biography with the help of his friend and frequent collaborator, director Carey Perloff, who through August will stage a slightly scaled down version of the work in its Midwest Premiere at Writers Theatre in Glencoe.

“Tom Stoppard had a very complicated life, much of which he didn’t know that much about as an adult,” said Perloff. “He had gone around saying that he’d led a charmed life, which he had in many ways, and he was the most charming, resilient, positive human being you’ve ever met, but he then felt terribly guilty that he hadn’t understood what had happened to his family.”

In real life, all four of Stoppard’s grandparents were killed in the Holocaust. In the play, a Jewish family in Vienna is chronicled for 50 years spanning before and after World War II.

“Leopoldstadt” first premiered at Wyndham’s Theatre in London in 2020, before going to Broadway in 2022 and racking up the awards. And while it would sound crazy for any off-Broadway theater to put a Broadway-sized production on an intimate stage, that’s what Writers is doing.

The Writers’ version of the epic family drama boasts a cast of nearly 30 performers, requiring 475 costumes and 35 wigs for the production that spans 1899 to 1955.

The key ingredient is Perloff. She’s been a collaborator with Stoppard for more than 30 years. “Pinter and Stoppard: A Director’s View,” her book on the prolific writer, published in 2022. In it, Perloff reflects on working with Stoppard and another fellow playwright of renown, Harold Pinter.

With “Leopoldstadt,” she worked with Stoppard directly to figure out the doubling and cutting of ancillary characters to ensure the production would work off Broadway.

“We sat at his dining room table, spread out the script,” she explained. “Took characters, reassigned lines — I have those pages from Tom all marked up. It’s moving to me. I wish he was here. It’s the first Stoppard play that I’ve directed in 30 years that I can’t pick up the phone and call him.”

Just weeks before the Midwest premiere — which cost Writers $1.3 million to secure — the design teams are hard at work.

“This play has only been done in large Broadway-style houses up until this point,” said artistic director Braden Abraham. On a private tour backstage in late May, he pointed out the additional staff needed to make it work. There are 14 people making the costumes — Writers usually hires five at most. They also had to bring in a wigs team, with three staffers, and a few extra hands on the wardrobe crew. “So, what we’re doing here is a first. We’re taking this play of enormous size and scope, and we’re putting it in our intimate 250-seat theater.”

An additional concern for a production spanning so many years, with so many characters, is ensuring audiences can follow the story. Perloff said that’s part of the show’s charm.

“Here’s the challenge,” said Perloff. “It’s like reading a Russian novel. You have to give yourself permission that you will not remember that Sally and Rosa are Vilma’s children. That’s okay. Because otherwise you’ll spend your whole time looking at the genealogy in the program.”

Chicago’s pool of talented actors helps the director pull off casting individual performers in multiple roles across the acts.

“These Chicago actors are like nothing else,” said Perloff. “I have worked in a lot of cities. They are remarkable. But in addition to their individual talent, what makes it different in Chicago is that they really are like a company, because this town employs its own artists. It’s not about how many celebrities we can get from L.A. So, in the room together, they’re very brave, and they’ll go the distance.”

Perloff described a scene between Steppenwolf ensemble member Ian Barford as he squares off with Lookingglass ensemble member Joey Slotnick. “First of all, they’re hilarious,” she said. “But they just go toe-to-toe. They’re not scared of each other. It’s fierce.”

Like Stoppard, Perloff said she has her own personal connection to the production.

“This play is so personal to me, because in so many ways it’s also my mother’s story,” she said. “This Viennese family, highly cultured intellectual, was really her family, much more than it was his family.”

But Stoppard did write himself into his own play, she pointed out.

“There is a character called Leo, who was Leopold Rosenbaum and has changed his name to Leonard Chamberlain, and that is the Stoppard character,” said Perloff. “I thought it was incredibly brave that he wrote that scene, because it’s quite self-lacerating. I mean, the guilt that this character feels at his ignorance of his family trauma is palpable, and it’s really moving, and it takes a lot of guts to write that.”

Even with the heavy subject matter that covers themes of belonging and assimilation, the grief and loss of the Holocaust and the horrible aftermath, the play will still deliver plenty of joy, Perloff said.

“Here’s what I loved about Stoppard,” she explained. “He never took himself too seriously, and he always found mordant humor in everything. So, there are a lot of laughs in this play. There’s a lot of humanity. People will recognize their own behavior — and their own families.”