‘Celebrity Chekhov’ Is as Much a Tribute as It Is an Invention

“What makes [Chekhov’s] stories,” Ben Greenman asks in the book’s introduction, “so compelling?”

A reinvention of some famous and some not so famous Chekhov stories, in Celebrity Chekhov, Greenman recasts the original characters with contemporary actors, politicians, socialites. I wondered if this book would be more in line with the hilarious satire he’s so well known for over at McSweeney’s Internet Tendency, but surprisingly Celebrity Chekhov is (as Harper Perennial put it) “more than just a literary stunt,” and is “a surprisingly compassionate window into a set of lives that have traditionally been considered tabloid fodder at best.”

So what makes Chekhov so compelling? Greenman’s response: “Chekhov understood people particularly well, and specifically he understood their weaknesses.”

I haven’t owned a television in nearly a decade. I do, however, flip through trashy magazines while waiting in line at Duane Reade. This is to say that I am familiar with Paris Hilton, Michael Douglas, Simon Cowell, and even Gary Busey (who makes a sad and seemingly perfect fit in the story “Terror”). The lack of knowledge, or even interest, in these public figures is not why I worried about my ability to relate to this book. I worried about my deep connection to the Anton Chekhov; his stories, his plays; his unrelenting depiction of the human condition. Alas with sensitivity and compassion, Greenman, breathes a new life into these stories.

General Zakusin from “The Album” becomes Sarah Palin and in a hysterical moment, she allows her daughter, Piper, to make paper doll cutouts of the lieutenant governor and the adjunct general. In “At the Barber’s”, Billy Ray Cyrus, to the exasperation of the barber, admits having betrothed his daughter Miley to a sporting goods dealer. “Why I… why,” laments the barber, clippers on the table, Billy now half bald. “I cherished sentiments for her. It’s impossible. I am in love with her and have just recently sent her a letter offering my heart.”

That’s what the best of Greenman’s stories do: yearn. They bleed like only a Chekhovian character can.

This book is as much a tribute as it is an invention. Sure, a few of the stories fall short. In “Choristers” Randy Jackson and company fail to stand up to their Russian counterparts. Count Vladimir Ivanovitch is no match for Bono. Yet, in his defense, Greenman admits that “sometimes the [celebrity] fit is perfect. Sometimes it’s intentionally, surreally bad, and sometimes the pleasure is in the disorientation.” Unfortunately, I couldn’t find any pleasure in the disorientation of the American Idol tribe.

Or Eminem in “Hush” does very little in place of Ivan Yegoritch Krasnyhin, the struggling, overly wrought author in need of peace and quiet in order to create. Aside from our ability to pronounce Eminem’s name with ease, the story simply lacks in the humor I’ve grown to expect from Greenman.

Most of these stories, though, sing with Greenman’s caustic wit, and they dance with love and sadness: Nicole Kidman in “The Darling” loses Tom Cruise to an unfortunate and unknown death. She finds love again — this time with Keith Urban, a lumberjack. When she loses him, too, who’s left? Brad Pitt’s son, of course.

This is when Greenman is at his best. His humor moves from morose to laugh out loud funny, to tears in your eyes as you read. He has complete control over timing. It moves to his pulse and the reader moves with it. Beat by beat.

The very best, the very, very best of these stories make us weep: Lindsay Lohan’s mother pleading with Jesse James to give her daughter a “good flogging” as she’s clearly let down the entire family; no new movie rolls, no longer in fashion, and a failed attempt at Shakespeare! Lohan is painted as the great failure, after all, from Gawker to Greenman.

Perhaps this was Greenman’s goal: to give the outer lives of these all too familiar celebrities some humane and internal qualities that the media can’t depict. Such as real sadness. Not the Britney Spears and Justin Timberlake who broke up a decade ago, but the Britney, years later in “A Lady’s Story”, who recognizes that her life has passed her by. “I was loved,” she says, “happiness was not far away, and seemed to be almost touching me…”

In “An Enigmatic Nature” Oprah says, “I yearned for something extraordinary, above the common lot of woman!” In “Bad Weather”, Tiger Woods’ lonely wife “waved her hands and burst into loud weeping, uttering, ‘Not at home! Not at home!’”

Much like Greenman’s previous collection, What He’s Poised To Do, the stories in Celebrity Chekhov take just a few minutes to read but stay with you long after. You’ll feel you need to return to them. They’ll pull you in that deep.

If they don’t, send me your copy of the book, I’ll put it in the mail and send it to a stranger as one reviewer did with Greeman’s previous book, because…why not?

Somewhere, someplace, someone loves Nicole Ritchie and has never heard of Anton Chekhov.