CHICAGO — Few nonresident playwrights have exerted a broader influence on Chicago theater than Richard Greenberg, the author of “Take Me Out,” “Three Days of Rain,” “The American Plan,” “The Violet Hour,” “The Dazzle,” “The Well-Appointed Room” and many other titles, a good number of which premiered at Chicago’s Steppenwolf Theatre in the early years of the 21st century under the artistic direction of the late Martha Lavey, for whom the whip-smart and verbally driven Greenberg was among the greatest living writers.

Prolific and intellectually restless, Greenberg was in many ways the loquacious American version of the late Tom Stoppard, and in turn a significant influence on such Chicago writers as Tracy Letts. When she wrote about “The Well-Appointed Room,” the fifth Greenberg play Steppenwolf had produced, the voraciously intellectual Lavey described Greenberg as “one of American theater’s most engaged and inquiring playwrights.”

Robert Falls, formerly Lavey’s opposite number at the Goodman Theatre, is also a longtime fan, even if Greenberg was more connected to the other big Chicago theater. ‘There is a rigor to Richard’s plays and a determination to go against any sentimentality,” Falls said. “His characters are armored. They debate. They fall in love. They fall out of love. Language is usually their best defense.”

So when Greenberg died last summer — from cancer and at the age of 67 — the mourning in Chicago theater circles was as palpable as in New York. As it was, of course, within Greenberg’s own family.

“Richard did not read his reviews from either Chicago or New York,” the playwright’s droll brother, Ed, said in a recent telephone interview. “But we did. And if anyone said anything negative about his plays, that was the address to send the anthrax.” The older Greenberg works in finance. “But I would always bring up Richard with my clients,” he said. “I was so very proud of my younger brother and all he accomplished.”

Ed Greenberg, who now supervises his late brother’s estate, will be in Chicago on Monday for the opening of Falls’ Goodman homecoming production of “Holiday,” the last Richard Greenberg play to be completed during his lifetime (although Ed said there were “four or five things on Richard’s computer,” yet to be mined).

“Holiday” is not exactly au fait with Greenberg’s other work.

For one thing, it is a new, contemporary adaptation of a 1928 Philip Barry play, a romantic comedy best known from its adaptations to film, especially the 1938 movie directed by George Cukor and starring Katharine Hepburn and Cary Grant. The movie is widely seen as a classic of the so-called “screwball comedy” genre, not a genre with which one immediately associates Greenberg. But his brother says that underestimates the eclecticism of his tastes and that Greenberg did not have any interest in baseball until he wrote “Take Me Out” and then turned immediately into an expert. “When Richard took on an interest, he devoured it,” Ed Greenberg said. “And he delighted in ‘Holiday.’”

“Holiday” follows a self-made investment banker named Johnny Case who meets an affluent woman named Julia Seton while on vacation in New York; the two plan to marry, and things complicate from there as Johnny’s plans for self-fulfillment rub up against the ideas of the woman’s rich father and her contrasting siblings come into play.

So what, exactly, did Greenberg do to this play? Modernized it, for one thing.

“It’s amazing how Richard succeeded in transporting the Philip Barry play to contemporary times in ways that are unique to Richard’s voice, while also making sure that it’s still ‘Holiday,’” said Miranda Barry, the playwright’s granddaughter, the keeper of his flame and an entertainment executive in her own right.

“Holiday,” one might reasonably say, is Barry’s second most famous play after another Barry work that also became a Hollywood classic, “The Philadelphia Story.”

“Richard follows the storyline of the original ‘Holiday’ very closely,” Miranda Barry said, “but the characters are completely contemporary. Julia is now a young entrepreneur with a wellness line. Her father is a more fully realized character. Richard’s style is both hilarious and all his own, especially his rhythm and wit.”

Barry, who was in Chicago watching rehearsals for several days, clearly viewed Greenberg’s work as ranging well beyond a polish or a mild update. “There is now a turning point where everything becomes much more serious,” she said. “Suddenly, everyone watching goes quiet because people are traveling on a journey to really think about whether it is better to live to work or work to live. It gets to the depths of the themes of this play that doesn’t fully happen with the original Barry play because it has all of this froth and zaniness.” The frothy zaniness was, of course, one of Barry’s Hollywood calling cards, but there always were serious themes submerged underneath.

Originally, “Holiday” was poorly timed. “It came out in 1928, just as the bottom fell out,” Miranda Barry said. “Nobody wanted to see a play about a man who wanted to stop working. So the tour was a disaster. But the times now are very different, obviously, and people are thinking about what really matters to them.”

The Greenberg and Barry estates, along with Falls, all share the same interested agent in George Lane, the legendary CAA deal-making personality, so that also explains this unusual marriage. And, indeed, there have been rumblings of a Broadway transfer already for “Holiday,” possibly with the addition of stars. A one-night benefit reading for The Acting Company in New York in the fall of 2024 featured Ella Beatty, Rachel Brosnahan, Lilli Cooper, David Corenswet, Hiram Delgado, Chris Perfetti, and the big draw John Slattery, of “Mad Men” fame. That doesn’t mean such actors would be interested in, or available for, a Broadway staging, or that Falls or a commercial producer would be interested in them, but “Holiday” has a long history as a star magnet.

Monday night in Chicago, though, will see the world premiere of the last ever Richard Greenberg play, at least until Ed Greenberg decides to face whatever remains on his beloved brother’s computer. The Goodman cast features Luigi Sottile, Molly Griggs, Jordan Lage, Jessie Fisher, Bryce Gangel, Erik Hellman, Alejandra Escalante, Rammel Chan, Wesley Taylor and Christiana Clark.

“This is simultaneously a Philip Barry play and a Richard Greenberg play,” Falls says. “If you came to the theater and had no idea who Philip Barry was, you’d just accept it as a contemporary Richard Greenberg play.”

Falls also said this is the first time in his long career he had worked on a new play without the playwright sitting next to him at rehearsal. “This is a new play and every new play I ever have done has been about me serving the playwright,” Falls said. “That’s still true here but this one can feel lonely. Richard is not here.”

But “Holiday” is there. Or, at least, arriving. A new Richard Greenberg play and perchance a new favorite for his older brother.

“We enjoyed all of Richard’s work,” Ed Greenberg said to the suggestion. “We would talk about our favorites every once in a while and we’d try to be objective. But really, that was just to show that we are smart, analytical people and not just emotional.”

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Through March 1 at the Goodman Theatre, 170 N. Dearborn St.; 312-443-3800 and www.goodmantheatre.org.

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