The Seagull: Can Chekhov be made our contemporary?

Constantine is now an angry performance artist in a Pussy Riot T-shirt, while Arkadina is a Stratford Festival actress who name-drops Christopher Plummer. Masha may still be all dressed in black and in mourning for her life, but now she deals with her sadness by taking tokes from a one-hitter instead of snorting snuff.

Toto Totoyevich, I've a feeling we're not in Czarist Russia any more.

Director Peter Hinton's new version of The Seagull – Anton Chekhov's 1896 tragicomic classic about unfulfilled artists and unrequited love on a crumbling estate – is what is generally referred to as an updated production. But the other way to think about it is that it is a production that restores the play's contemporaneity.

The Seagull was not originally written as a period piece, but a play set in the present. It is filled it with references to real Russians that, for his adaptation, Hinton has swapped for current Canadian ones.

So Arkadina (a preening and perfectly cast Lucy Peacock) brags about of acting with "Chris," while the empathetic doctor Dorn (a wonderful Patrick McManus) is accused of walking around like "he thinks he's Jian Ghomeshi or something."

This is a case of moving further away from Chekhov's words, but closer to his intentions – and the best part of the approach is that The Seagull, for once, actually seems like the comedy that the Russian playwright claimed it was. The first scene in which Constantine's performance is undercut by his mother's attention-grabbing outbursts is certainly laugh-out-loud funny – at least, until we realize that younger artist (played by Patrick Costello) is taking everything deadly seriously.

Indeed, Hinton's production is a study of the eternal generation gap between the seriousness of youth and the inherent comedy of age. Everyone's in love with someone elusive, at least emotionally – the estate manager's daughter Masha with Constantine; Constantine with girl-next-door Nina; Nina with the writer and Arkadina's lover, Trigorin; Arkadina with herself – but it's only the young characters who pay a price.

Eo Sharp's striking if somewhat clumsy set gives us two patches of trees with scribbled-upon panels in between. At first, Hinton's staging is similarly non-representational – with Constantine pushing a moon made out of an exercise ball hanging on a long rope into the sky.

Gradually, however, the production becomes more tethered to reality and the problems with Hinton's adaptation begin to dilute its pleasures. These 21st-century Canadians with Russian names fit uneasily in this late 19th-century four-act dramatic structure.

Instead of being set on an estate, this Seagull takes place on the Niagara fruit farm turned winery owned by a retired judge named Sorina (Diane D'Aquila). Her antagonistic relationship with the winery's mad manager Shamraev (Michel Perron, over-the-top as per usual) never quite makes sense. Likewise, Simon Medvedenko, the penniless schoolteacher rejected by Masha, is hard to believe in this context – and not just because the effortlessly charismatic Andrew Shaver has been cast in the role, looking dapper in an Expos cap. Who wouldn't want to marry an Ontario schoolteacher today? Pension city!

For me, the final straw was when Constantine was praised for getting a story published in Saturday Night magazine. I was plunged into a the character's black moods upon realizing that this production made it to the stage without a single person involved pointing out that periodical sadly stopped publishing in 2005.

In short, Hinton's script is in need of another draft and an outside pair of eyes – as well as 40 minutes of fat trimmed from its over three-hour running time. Then it might be sensational, rather than a slog. But the production has its appeals, especially the younger actors: Krista Colosimo walks around as if she's always dragging a weighted-down scarf behind her as Masha; Costello is a bent nail that just can't straighten as Constantine; and Shannon Currie is truly gull-like as Nina, circling the stage, her eyes darting out in all directions, desperately looking for a safe place to land on this hostile estate.

Follow me on Twitter: @nestruck