There is a profoundly—and unintentionally—fucked-up moment toward the end of Vanya and Sonia and Masha and Spike, Christopher Durang’s aggressively frivolous riff on Chekhov set in modern-day Pennsylvania. The themes are physical comfort and metaphysical discomfort, naturally, and the plot concerns two aging siblings (Vanya and Sonia), who’ve been living in the old family home off the largesse of their movie-star sister (Masha), and what happens when they learn that they might have to get jobs and apartments of their own.

To complicate the picture, Durang has added three other characters: Spike, Masha’s young, pretty, and idiotic boyfriend whose main accomplishment is having been “almost cast in the sequel to Entourage”; Nina, an earnest aspiring actress who’s visiting her aunt and uncle next door and drives the aging starlet Masha bonkers with jealousy; and Cassandra, who Durang describes at the top of the script as “cleaning lady and soothsayer, any age, probably African American.”

Cassandra is literally a “magical Negro,” that literary cliché described by Spike Lee, Heather J. Hicks, and other cultural critics back in the early 2000s as the token black figures who typically occupy a lower economic station (the archetypal example is Will Smith’s mystical golf-caddy character in The Legend of Bagger Vance) and exist solely to assist white and wealthy protagonists on their quests for inner fulfillment.

Durang doesn’t seem to have gotten that particular memo—Cassandra isn't some self-aware commentary on that old phenomenon. She is the phenomenon.

While Vanya’s white characters fret about money and ennui, Cassandra cleans up after them and occasionally launches into prophesies: “Beware the Ides of March! … Beware the middle of the month! Beware Greeks bearing gifts! … O fools looking behind but not looking ahead, dost thou not sense thy attendant doom?” (Vanya responds with mild irritation: “I have asked you repeatedly to just say ‘good morning.’”) For the play’s climactic moment, she comes in to work on her day off because, as she explains to Vanya: “I’m worried about you and Sonia. I had presentiments last night.” I know this is supposed to be a zany comedy and all, but details like the “magical Negro” housekeeper volunteering to work on her day off because she’s had “presentiments” about her employers are about as disconnected and insulting as President Bush being awestruck by a grocery-store checkout scanner back in 1992.

That’s the backdrop for Vanya and Sonia and Masha and Spike’s profoundly fucked-up moment.

Quiet and agreeable Vanya, like any good Chekhov character, has secretly been working on a play. Nina insists on a group reading, Spike texts his way through the beginning, and Vanya asks him to stop. “I can multitask,” Spike says. “I can drive and text, or watch a movie and tweet.”

This sends Vanya into a 1,500-word monologue (longer than this review) that’s equal parts bitter about the present and nostalgic for the 1950s: “You can multitask, how wonderful,” Vanya begins. “You twitter and tweet, you e-mail and text, your life is abuzz with electrical communication… There are 785 television channels. You can watch the news report that matches what you already think. In the '50s there were only three or four channels, and it was all in black and white. And there were no child stars who became drug addicts like Lindsay Lohan… We licked postage stamps!”

On and on and on he goes, unspooling his nostalgia for the 1950s and the wretchedness of the 21st century while Cassandra sits and smiles through his rhapsody about Old Yeller, Davy Crockett, Ozzie and Harriet, and the decade before the Civil Rights Act was passed. Vanya doesn’t mention that, but I watched Cassandra's face throughout his tirade, wondering if that thought was dammed up behind her fixed smile. “Now, now there’s twitter and e-mail and Facebook and cable and satellite, and the movies and TV shows are all worthless,” he concludes. “We don’t even watch the same worthless things together, it’s all separate. And our lives are... disconnected… I’m worried about the future. I miss the past.”

It’s the theatrical equivalent of click-bait for white, middle-class geezers. When Vanya was finished, the overwhelmingly pale opening-night audience gave him a big round of sympathetic applause.

Which is not to say that Vanya, et al. is a thoroughly rotten script. Durang plays with frivolity the way a math prodigy might play with a Rubik’s Cube—he's serious about his games—but frivolity can be a dangerous thing when it’s not aware of its own fatuousness. Take, for example, the plays of Yasmina Reza (Art, God of Carnage), which are so self-absorbed with upper-middle class nothingness that they become grotesque and offensive. One counter-example is the TV show Curb Your Enthusiasm, in which Larry David investigates and mocks the delicacy and solipsism of the highly privileged. Another is, well, Chekhov.

The performances, directed by Kurt Beattie, are all clean and bright—R. Hamilton Wright as the slightly brittle but mostly genial Vanya; Pamela Reed as Masha, who’s exhausting herself by trying to seem vivacious and carefree; and Cynthia Jones as an exuberant and obliging Cassandra. Marianne Owen gives a particularly good performance as the sad-sack Sonia, and provides a nuanced emotional taxonomy of her character’s low-volume existential crisis. (In one of the play’s sharpest exchanges, she tells her brother Vanya about her bad dreams: “I dreamt I was 52 and I wasn’t married.” "Were you dreaming in the documentary form?” Vanya responds.)

To its credit, Vanya and Sonia and Masha and Spike opens with the beautifully tense, high-stakes politeness of Chekhovian comedy, as Sonia brings her brother Vanya his morning cup of coffee. Their parents were professors who were deeply into Chekhov, and jet-setting Masha pays the bills, which explains a few things about the two siblings: their names, their ability to survive comfortably in the family home without working, and Sonia’s anxious refrain that “we are in our twilight years, and we realize we have never really lived.” What she means is that they’ve never really struggled. They are kept creatures in a hermetic world, without the joys and strife of work and romance to fill their days, so they freak out over the little things:

SONIA: I brought you coffee, dearest Vanya.
VANYA: I have some.
SONIA: Oh. But I bring you coffee every morning.
VANYA: Well, yes, but you weren’t available.
SONIA: Well, I was briefly in the bathroom, you couldn’t wait?
VANYA: I don’t know. The coffee was made, you weren’t there, I’m capable of pouring coffee into a cup.
SONIA: But I like bringing you coffee in the morning.
VANYA: Fine. Here, take this cup and give me that one.
SONIA: Alright. Now I feel better.
VANYA: I’m glad… [sips the coffee] I’m afraid the other cup tasted better.

This exchange escalates—“you’re implying I don’t do anything right,” “I didn’t say that,” “yes you did”—until Sonia has thrown both cups of coffee against the wall and exclaimed: “I have two pleasant moments every day in my fucking life, and one of them is bringing you coffee!” Owen and Wright execute this dance with perfectly restrained calibration, making the first 10 minutes or so of Vanya and Sonia and Masha and Spike a bracing, tiny tragicomedy about small details that falls firmly in the same Chekhovian lineage as Alice Munro—or, for that matter, Larry David. It would have been almost perfect on its own.

Alas, there was more.