Francis Guinan, Kate Fry and Christopher Donahue Photo by Liz Lauren

In 1904, Chekhov wasn't thinking about how The Cherry Orchard would fare in decades and centuries to come. He was writing for his own contemporary audiences and for directors who often clashed with him about how to interpret his work. (Famously, Konstantin Stanislavski directed this play as a tragedy while the author considered it a comedy.) Goodman Theatre's outgoing artistic director Robert Falls–whose sparkling career has already featured productions of Three Sisters, Uncle Vanya, and The Seagull, completes his journey through Chekhov's best works with a very funny and very tragic The Cherry Orchard that includes a veritable Who's Who of some of Chicago's finest actors doing their finest work.

The plot is pretty straightforward and very Chekhovian: a formerly aristocratic family, owner of a decaying estate and its famously grand cherry orchard, is faced with bankruptcy unless they can be persuaded to sell off the land and build summer cottages along the river that runs through it. Perfect reflections of the idle rich, they simply can't bring themselves to destroy such an important part of their history, even knowing that the date for the land auction has been set and it will all be destroyed anyway. Instead of taking steps to avert disaster, they pretend everything will just take care of itself. They spend money they don't have; they throw parties they can't afford. But they can't see that the era that spawned all of this is coming to an end.

Within this setting, there are many interesting characters and relationships, but the bottom line is that this family is incapable of moving on, victims to the same kind of inertia that Isaac Newton wrote about: unless an outside force can act upon them, they will remain in stasis, even to their own detriment.

Yermolai Lopakhin (Kareem Bandealy), a successful local businessman whose father and grandfather were serfs on this same estate, tries his best to be that outside force, but Lyubov Ranevskaya (Kate Fry in one of her best performances), the flighty current owner of the estate, refuses even to consider his proposal, and her brother Leonid (Christopher Donahue), a man whose only passion seems to be billiards, lacks the force and foresight to change her mind. The two grew up on this estate and see it (and especially its orchard) as part of their lives, part of their family. Unable to imagine that it could ever be taken away, they both await some kind of deus ex machina to intervene for them, but the truth is that they have squandered everything they once had and know no one (save Lopakhin, whom they won't listen to) who could save them from their own folly.

Chekhov populates this work with all sorts of wonderful and eccentric minor characters. Francis Guinan is Firs, the 87-year-old butler who remains fiercely loyal to Lyubov and her family, which also includes two daughters, 17-year-old Anya (Raven Whitley) and 24-year-old Varya (Alejandra Escalante), the adopted daughter who takes care of the estate–or anyway would do so if her mother would stop randomly giving all their money away. Janet Ulrich Brooks steals the show as Charlotte, a governess who rides the estate on a bicycle, watching over it with a handy shotgun, and is quite adept at sleight of hand magic, which she is always happy to show off. Her magic, of course, is all illusion, an intentional echo of the magical thinking of Lyubov and Leonid. No one can or will help them–even the one relative who sends money can only afford 15 thousand rubles when they need at least a hundred thousand–yet they keep believing in a miracle.

Matt DeCaro plays Boris, a neighboring estate owner who is always asking everyone for a loan. Stephen Cefalu plays Petya, a perpetual student who, despite his attraction to Anya, only has room in his heart and brain for revolutionary philosophy. Two servants–Felipe Carrasco's morose and self-involved Yasha and Amanda Drinkall's wonderfully ebullient Dunyasha–round out the estate's regulars along with Will Allan's über-clumsy Yepikhodov, a bookkeeper in love with Dunyasha who provides a lot of comic relief.

The center of Todd Rosenthal's set is a rolling platform holding the family's now-unused nursery. It is lovely and contains many props that Rosenthal can be proud of finding, but it is one of the seasoned designer's few misses: its squared shape means that both of the side walls are cut off for specific subsets of the audience. The left side misses most of the sitting space in the room, while the right misses out on the windows, which play a key role in the family's reminiscence. A third-act ballroom set fares much better.

Falls has chosen his swan song well. This is a play about looking back to see what once was and reflecting on what might never have been. In a modern, changing world in which many people have lost their sense of place, there is a tendency to embellish the memory of the past, to overlook the issues and problems that defined it as much as any joy or laughter. In The Cherry Orchard, Falls captures that moment of change in all of its confusion and pain while keeping one eye on what makes the past nostalgic and romantic. Letting go of this place, like letting go of the estate, cannot have been easy but, as with The Cherry Orchard itself, change is inevitable.

The Cherry Orchard runs through April 30, 2023, at the Goodman Theatre, 170 N. Dearborn, Chicago IL. For tickets and information, please visit www.goodmantheatre.org.