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TIFF Shinan Govani: Having Jake Gyllenhaal at the party may beat actually rubbing elbows with him

I watched the man who created Don Draper gingerly shuffle into a place where he could get a good view.

“There he is,” said Matthew Weiner to the gentleman he was with, pointing to one Jake Gyllenhaal, as every atom in the place also swooshed to the bearded fella standing in the corner of Patria, here off King West.

Weiner, who brought existentialism to a whole new peak when he created TV’s Mad Men, looked somewhat forlornly at Gyllenhaal, then took a swig of something in his glass. There was a banquette, and a pillar of sorts, separating him and Gyllenhaal, in this restaurant where paella is usually in motion, the lighting is Streisand-worthy and a fabulous embroidered mosaic drapes much of the back.

“Let’s go,” said Weiner’s accomplice. Weiner ceded. They reshuffled. That song that put the words “Nae Nae” into the musical ozone this summer played not long after.

Jake Gyllenhaal (Stefanie Keenan/Getty Images for Grey Goose Vodka)

It seemed that having Gyllenhaal at the party was as good, if not better, than actually rubbing elbows with him, as is so often the case when one is in a room with celebs. Because even for a “celebrity show producer” who created one of the greatest shows ever – what does it count? I was there: what being at a party with a real movie star, more often that not, amounts to: It’s metaphysical, man.

Maggie’s baby bro sloped into the TIFF party, hosted by Grey Goose, just after the unspooling of his opening night film, Demolition. With the slicked-back hair routine, well-fitted suit, and the extra bulk he’s carrying of late, his style, as I’ve opined before, was in the vein of old-school Italian mogul Gianni Agnelli. It worked. Making the scene at the fairly boisterous party, too: the director of the somewhat bonkers film, Canada’s Jean-Marc Vallée. So, too, a two-pack of other cool directors – Jason Reitman and Denis Villeneuve. Co-star Chris Cooper hung back in the little outside alley of the restaurant. Looking zen, and pulling off a many-tiered ruffled dress courtesy of Balmain: Naomi Watts. As far as ruffles go, she was giving Frito-Lay a run for its money … and looking great.

Jake Gyllenhaal and Naomi Watts (Stefanie Keenan/Getty Images for Grey Goose Vodka)

As the party broke off into different tentacles – with many people using both hands to hold saucer-sized glasses of Grey Goose Le Citron with a pinch of basil – we noticed that Gyllenhaal’s first and last check-in at the party was with his agent, Patrick Whitesell. Scratch that. Superagent. Whitesell, it’s clear, has been instrumental in creating the recent Gyllensance of sorts. After a career that parachuted off in the early naughts – one that climaxed with an Oscar nomination for Brokeback Mountain some years later, but then grew somewhat aimless with his movie choices – the personable actor has had an over-and-beyond streak of late with movies like Nightcrawler, Southpaw, End of Watch, Enemy. And now, Demolition. As Grantland put it recently in a career biopsy, his recent movies are “notable for the degree to which it seems motivated solely by his evident pleasure in doing whatever the hell he wants...” And to think, this is only his second big film festival premiere this week...! A few short days ago, he was in Venice to premiere his other hot project, Everest.

Jason Reitman (left)) and Jean-Marc Vallée (Stefanie Keenan/Getty Images for Grey Goose Vodka)

When Gyllenhaal goes to the Academy Awards again as a nominee some day – and, at this point, it looks like when, not if – he’ll be ready. In fact, there are probably two things we can count on with the guy. One, that he’ll win a gold statue at some point. And, two, that he’ll get married. “I believe in monogamy,” the extra-eligible bachelor told Howard Stern in an interview a couple months back. “I believe in when you meet somebody who’s right, like, it’ll be right.”

Gyllenhaal, who’s been evidently focused on his career of late, but has dated beauties ranging from Taylor Swift to Kate Bosworth in the past, told Stern, “I love love, man.”

Conrad Black and Stephanie Seymour (George Pimentel)

Meanwhile: Even Baron Black of Crossharbour is not immune to the lure of parties this week. When The Room hosted an intimate dinner, inside Hudson’s Bay on Queen Street the other night for Stephanie Seymour – star of a new campaign for the elevated fashion space – the former media baron and prodigious writer of biographies made a solo appearance. Being introduced to the 1990s-era supermodel, Seymour was heard to say to Black, “I’ve read about you.”

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