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Ravi Jain, a Toronto-based director, is one of five shortlisted for the Siminovitch Prize in Theatre.Glenn Lowson/The Globe and Mail

The competition is tougher than ever this year for the $100,000 Siminovitch Prize in Theatre – for a couple of reasons.

The first is that for the first time, the jury for the richest award in Canadian theatre has expanded its shortlist to five nominees – two Torontonians, a couple of Quebec-based artists and an Edmontonian maverick. Previously, only four directors were picked.

"The entire field was really, really strong," says Bob White, head of new plays at the Stratford Festival and chair of the Siminovitch jury, which also included director Micheline Chevrier, translator Linda Gaboriau, playwright Mieko Ouchi and director Sarah Garton Stanley.

Jonathan Christenson, artistic director of Edmonton's Catalyst Theatre, whose macabre musical hit Nevermore recently had a run off-Broadway, tops the alphabetical list of finalists the jury will officially announce Mon-day.

Next is Ravi Jain, who recently had great success rediscovering Salt-Water Moon at the Factory Theatre in Toronto and shepherding the premiere of a provocative new play called The Adventures of a Black Girl in Her Search for God at the Shaw Festival.

Christian Lapointe, the in-our-face Québécois director whose works are favourites of the Festival TransAmériques and who recently caused a sensation at the Théâtre du Nouveau Monde with Pelléas et Mélisande, follows.

Fourth on the list is Ross Manson, long-time head of Toronto-based Volcano Theatre, which is touring Hannah Moscovitch's play Infinity around Ontario this season.

Nadia Ross, who, based out of Wakefield, Que., tours postdramatic performances around the world with her company STO/Union, closes it out.

In a way, the expanded Siminovitch shortlist properly recognizes that the art of direction has also expanded in English Canada since the prize was inaugurated in 2000 (lagging behind French Canada in this regard).

The nominees aren't just directors who know how to put a script up on its feet, but auteurs who are the essential creators of a show, agent provocateurs seeking to challenge existing audiences and innovators looking to find new forms to engage new audiences.

It's the diversity of directorial practice encompassed by the work of Christenson, Jain, Lapointe, Manson and Ross that is the second reason the 2016 Siminovitch jury has a difficult job ahead of it.

"It's kind of apples and oranges," admits White.

The Siminovitch Prize in Theatre is what White calls a "forward-looking" award, honouring artists somewhere in the nebulous middle of their careers as much for what they're going to do as what they've done already.

"It feels like what you're doing is putting some extra wind under a person, so they can take off a bit more and have a bigger profile," says White.

The Siminovitch is given out on a three-year cycle to directors, playwrights and designers – with the winner choosing a protégé to receive a third of the cash prize.

All five finalists for this year's directing prize will be celebrated with a reception at Hart House in Toronto on Oct. 17 and the recipient will be revealed to the world Oct. 28 in Ottawa at the National Arts Centre, where former Siminovitch Prize winners run both the English Theatre (Jillian Keiley, 2004) and the French Theatre (Brigitte Haentjens, 2007).

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