In our last look at the colourful world of TIFF parties, we head to The Roosevelt Room—TIFF’s silent party star—to pick up our bunny ears and toast Playboy’s newest cover girl, Toronto’s own Charlie Riina.
In certain circles, there’s a little pastime known as PnP, or Party and Play. So when, during the dénouement of TIFF, an invite comes to party and play (professionally, of course) with a newly-minted Playboy star, one can’t help but (reluctantly) trade in those tickets to Wuthering Heights and cordially accept. But we’ll get to that part soon enough. To be frank, I was more thrilled by the chance to finally land at The Roosevelt Room Supper Club, one of the festival’s busiest, yet surprisingly underrated, venues.
When Ken Bryan and Anthony Miceli opened the Room in November 2009, they knew exactly what they were doing. Tucked away, almost annoyingly hidden, in an alley off Adelaide West, a stone’s throw from the city’s wavering club district, the project was modelled after the 1920s Roosevelt Hotel in Hollywood, the original setting of the first Academy Awards ceremony in 1929. The place pays homage to that era of old Hollywood—from the floors to the curvy lines that illuminate the décor—and there’s barely a hint of that modern, outright opulence you find at many of the city’s other supper clubs.
That’s why you’re not quite sure what to make of The Roosevelt Room; its dinner service has been steadfastly improving with each new season and each new chef, but the programming doesn’t always deter bass-thumping, fist-pumping bros either. It’s not uber-exclusive like the SoHo House that popped up on Duncan Street for TIFF’s first four days, and not nearly as painful as Nikki Beach. It’s decidedly Toronto’s own touch of class.
But the venue does have something in common with its terribly temporary TIFF contemporaries: its proximity to the Bell Lightbox a.k.a. festival central. This little detail was carefully considered by the owners, with a lease that was signed to practically coincide with the announcement of the Lightbox itself. I mean, it’s no big deal, really; you can frequent RR whenever you want. There’s just something about the damn place during TIFF that seems to actually make sense.
In fact, the Roosevelt Room has become the veritable silent star of TIFF’s party hoopla. In its short two-year tenure, it’s has managed to accumulate a throng of star sightings, yet has remained under the media’s radar as an “It” hotspot. This year alone, the Roosevelt has been an anchor for cast dinners and after-after party shindigs. Spotted throughout TIFF ’11: Colin Farrell, Ethan Hawke, Gerard Butler, Juliette Lewis, Anna Kendrick, Chace Crawford, and, duh, Dave Matthews. And we’re not talking the simple “come in, circle the joint, take a few pictures, and leave” type thing. The aforementioned have actually had dinner chez Roosevelt, attracted by Chef David Rocco and his exquisitely crafted menus. (He’s also done the Room’s fall 2011 menu that’s now being served post-TIFF.) So, of course, I’d like to try that new Roosevelt Room menu and hang out at an impending sausage fest.
But first: the curious case of Charlie Riina.
8:30 p.m.: I’m 30 minutes late, but the star of the hour isn’t even here yet. There’s a small turnout for what I’m pretending (in my head) is a “cast dinner” since I’d been itching to report from inside one all festival, and somehow missed them altogether. There’s one long table in the centre, and a cluster of smaller ones surrounding it—but not too close, no. To my amusement, two Macleans staffers are here to cover this thing, too.
8:43 p.m.: It’s a guessing game: when Riina will get here, whom she’ll bring and what they’ll all wear. I mean, what sort of thing does one wear to a Playboy fête? Cutting to the chase: “Well, I’ve already seen her naked, so….” (Google for yourself, hello.) Circulated guesses include: tube tops, bunny ears, sequins of some kind, short shorts, highest heels. It’s not mean-spirited or anything, but seriously: am I too overdressed for this thing? We’re also discussing which cover of Playboy Ms. Riina will grace. Turns out, it’s a special edition of the Nudes series for its October/November 2011 issue. What does that mean? From what we (everyone here, and online) can tell: no enhancements, 100 per cent natural ladies. I’m relieved we’re all sitting together, but I can’t get past the whole “Macleans is here?” thought.
9:30 p.m.: Chef Rocco’s new menu is served: Quinoa mango salad, tequila shrimp, Cornish hen, chocolate mousse, braised ribs. We’re talking about Maggie Gyllenhaal and Hugh Dancy. They tried this very menu last night at the Hysteria cast dinner. (“Maggie loved the mushroom risotto.”) There are also custard tarts so delicious that they’re second only to those found at Nova Era Bakery in Little Portugal. (Oh dear, please don’t let this be the highlight of my night.) The guest of honour finally arrives with a gaggle of men in suits and only a few girlfriends in tow (“her closest friends,” we’re told). One is, in fact, wearing short shorts. Riina herself is, in fact, wearing a sequined halter. Check, check.

10:43 p.m.: I’m escorted to Charlie Riina’s table. Our entire three-minute conversation goes like this:
So, what’s it like being part of the whole Playboy empire?
It’s extremely exciting and a little bit overwhelming.
And you’re from Toronto, right?
I was born in Poland, but I live here now.
Are you going to relocate to L.A. or something, or are you here forever…?
No, no, I looooove Toronto. [I find out later that she lives in Etobicoke.]
I heard that you revealed on ET Canada earlier this week that you parents don’t even know about this yet?
Yes! And they still don’t.
Not big fans of ET, I guess. Are you ever going to sit them down and tell them, “Look, this is what’s up”?
No, I want to surprise them.
Let them figure it out?
[Laughs] Yeahhhhhh!
Okay, but doesn’t that scare the shit out of you?
A little bit, but I like that. [I find out later that she also has an older brother who also doesn’t know about the pictures.]
What’s the hardest part about being admired by thousands of men?
There is no hard part, I love it. Wouldn’t you?
What do you do for a workout?
I’m all about boxing. Strictly.
Who’s the most interesting person you’ve met throughout all this?
Hugh Hefner!
Oh yeah? And what’s he like these days?
He’s amazing—very humble, nice, and actually funny.
What’s the biggest misconception about being a Playboy star?
That you have to be bleach blonde with fake boobs. When I did the cover, I was a brunette.
How did you end up doing this?
One day, I decided I wanted to try to pose for Playboy, and I did. And then they called me, and said, “You’re on the cover.” Okay, cool.
Next steps?
Working for Playboy still, and trying to get into movies.

10:58 p.m.: Guys who have lined the street outside for a meet-and-greet begin to trickle in. The tables are flipped; it’s all bottle service now. Of course, we’re ushered off to the side. Some girls—either Riina’s friends or waitresses, I can’t quite figure it out—emerge dressed in the “bunny uniform” (See: The House Bunny.)
12:15 a.m.: People are getting ridiculoussss. Pour, pour, shot, shot, snap, snap. “Dude, she’s fucking solid” is also happening a lot. Ukrainian DJ Juicy M. (flown in specifically for this event) is waiting to hit the decks. Fuck, she’s just as gorgeous, too. More guys going absolutely nuts. I’m told I must stick around because Juicy M is “amazzzzinnng.” I do, and she’s good. Good enough for right now—like, I’ve-had-three-vodka-martinis-so-I’ll-totally-dance-to-Jay-Z good.

12:30 a.m.: There’s an outfit change for Riina, who seems to be having fun: posing for pictures, getting creeped, PnPing up a storm. Girls are dancing like they’re a Lohan trying to get on TMZ. Guys have their “hunting face” on. Someone asks if I’m Perez Hilton. If tonight were a film, I’m pretty sure you’d call this part anti-climatic.