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Ninety firefighters worked to put out the blaze that gutted 116 Avenue Road, home of the restaurant Sotto Sotto. Officials are treating the fire as “suspicious,” saying that it could take several months to determine the cause.Hamilton Greenwood

On Christmas night, a still-unexplained fire destroyed the building at 116 Avenue Rd., home to Spuntini restaurant on the top floor and the aptly named Sotto Sotto (Italian for underneath) in the basement.

Many Yorkville residents were tipped off to the three-alarm disaster via the throngs of smoke and screaming sirens. Ninety firefighters worked to put out the blaze, which officials are treating as "suspicious," saying that it could take several months to determine the cause. Some 5.6 million others got the sad news via a different source – Drake's Instagram. The rapper and devoted Toronto booster posted an in-memoriam style snap of Sotto Sotto. "My second home," he called it, and he wasn't exaggerating. In recent years, Drake has shown serious love for his top hometown haunt, name-dropping it in two separate songs. He has been spotted dining there almost as frequently as he's seen courtside at the Raptors game – the latest in a long line of A-listers who helped to turn a subterranean shoebox into much-loved Toronto institution.

The space began its culinary life as Sisi, also an Italian neighbourhood spot opened by Leo Schipani in the late eighties. It became Sotto Sotto in 1993, after Mr. Schipani fell on hard times and sold his restaurant to its current owner, Marisa Rocca. "It" status came swiftly with a mixed bag of bold-face fans: Michael Jordan, Jason Priestley, Tony Danza, Dean Cain, Ellen Degeneres and Anne Heche, to name just a few era-defining celebs who spent time there.

A lot of the allure was geography: Sotto Sotto was located steps away from the Four Seasons, which meant L.A. imports could stroll over without putting too many miles on their Manolos. And lot of it was timing.

"It certainly didn't hurt that the birth of Sotto Sotto coincided with the explosion of TIFF, in the nineties," says Shinan Govani, who covered celebrity comings and goings for the National Post back in Sotto's heyday. Mr. Govani adds that the star power that swooshed around the restaurant during the film festival carried over to celebs shooting in town throughout the year.

"That reached a kind of apex in the early aughts – in 2001, The New York Times reported, that there were about 40 TV and film projects shooting in Toronto at one time," he says. The final piece was that ineffable matter of ambiance: In many ways, Sotto Sotto was the first hipster hangout in the sense that it was casual and cool in the we're-not-trying-to-be-cool kind of way. The curb outside may have looked like the site of a "my car is more expensive than your car" competition, but inside celebs could relax and rest assured that their needs were taken care of.

"It was a very cozy place with nooks and corners and privacy, which was very attractive to celebrities," says Helga Stephenson, who was the director of TIFF just as Sotto Sotto was taking off. "There was also the fact that you could get great food, but you didn't have to be dressed to the nines – now that's just a given, but it wasn't then."

It truly is harder to name celebrities who have not Sotto'd at one time or another, to use a verb first coined by Toronto stargazer Rita Zekas: Justin Bieber, Brad Pitt, Bono, Bill Murray, David Beckham, Burt Reynolds, Brook Shields, Bruce Willis, Blake Lively, Ben Affleck – and that's just the Bs. Oprah Winfrey threw a private dinner during TIFF 2009. John Hamm hung out there at the height of Mad Men-mania the following year. Along with Hollywood royalty, the restaurant has also been frequented by at least one actual royal (Sarah, Duchess of YorkFerguson), many politicos (Stephen Harper, Justin Trudeau), several star athletes (Chris Bosh, Sidney Crosby, Donovan Bailey) and an artist formerly known as Prince.

"We are heartbroken over the loss of our restaurant that has been a part of the Yorkville neighbourhood, history and culture for more than 22 years," Ms. Rocca said in an official statement released on Boxing Day. After arriving in Canada from Italy in the late 1980s, Ms. Rocca began her culinary career as a dishwasher at another Yorkville restaurant, Fieramosca, and worked her way up. Sotto Sotto was her first restaurant, and one she says she plans on rebuilding. Management is currently appealing to long-standing customers to help to restore its friends and patrons database, which was lost in the fire.

For the time being, though, Drake will have to go elsewhere to "talk women and vino," as he rapped of the restaurant on his 2013 hit album Nothing Was the Same. In the case of Sotto Sotto, it seems like nothing ever will be.

MEMORIES OF SOTTO SOTTO

Shinan Govani, society writer

As a professional people-prowler, Sotto Sotto was a must – it was the kind of place you could walk in and spot Gordon Gekko dining with Mrs. Doubtfire, as was the case one night with Michael Douglas and Robin Williams – but it was also a tricky place for snooping, due in part to the fact that it was so incredibly snug. I remember one time Jake Gyllenhaal was in the restaurant. It was during the time that he was dating Reese Witherspoon, who wasn't with him, but was picking him up in a car from near the back door [near the kitchen]. Somehow, or another, I found myself back there and watched as "Mama" [owner Marisa Rocca's 70-something-year-old mother, and a legend at Sotto Sotto] elbowed her way in to have a pic taken with the V-necked Jake. Though, as one of the staff whispered to me, Mama didn't really know who Jake was – she just enjoys having a picture taken with famous people. Mama gave me a jar of her secret chili sauce that night. And off I went, into the night with condiments.

Joanne Kates, food writer

It was this crappy, dank little basement and in front every single night there would be a lineup of six or seven mouth-watering cars – a Porsche, a Maserati. Mercedes were ordinary. Their owners were so wealthy they didn't care about getting a ticket. The place became a celebrity magnet pretty quickly. This was when all of the stars still stayed in Yorkville during TIFF, and I think another thing that made it popular is that the food was relatively healthy. Celebrities are generally paranoid about gaining weight and in 1993 there wasn't a lot of healthy food in Toronto restaurants. Sotto Sotto never met butter or cream – their signature seasoning was balsamic vinegar and garlic – everything came with radicchio and balsamic. In Toronto, that was very new. It was also the people who owned it – Marisa Rocca and her family, who also worked there, who were very trendy and cool. They hung out with the customers in a way that was very hipster and not the norm. Back in those days there was still a subservience on the part of wait staff and chefs in Toronto. There was none of that at Sotto Sotto – they were making it clear that they were just as cool as you were.

Suzanne Boyd, editor-in-chief of Zoomer Magazine

The location – being right there on the Mink Mile – was key. It was cave-like, which made it kind of sexy. It was sexy to go down the stairs and just feel enveloped in this warmth and wine and pasta. For me, it was all about Mama's eggplant parmesan. She would only make it sometimes, and if she hadn't made it on a day that I would go in, I would be so let down. It was just so amazing. Sotto Sotto was the kind of place you could pop in for a quick drink or celebrate a big occasions – not a lot of restaurants are good for both. I met Drake there a couple of years ago, he was always swooping in at some point because he lives in the neighbourhood. It was a favourite of a lot of celebrities. You'd be at the table and turn around and oh, there's Bill Murray. Of course, it is! Sotto Sotto has just been a constant in my life for so long – breakups, boyfriends, it's always been there. I was actually supposed to have dinner there on Boxing Day. I can't believe it's gone.

Michael Budman, co-founder of Roots

Sotto Sotto was the go-to place for any celebrity who came into town. Marty Short loved it, Mark Wahlberg, Lorne Michaels, Wayne Gretzky. I started going back when it was Sisi. It's hard to imagine now, but back in the late eighties and early nineties it was the only restaurant in Toronto that was open on a Sunday night and it was the same when Sotto Sotto opened. I loved to take my family there for dinner. It was so cozy on a cold winter's night and the food was delicious. The antipasto Gordonia was world-class. The other thing that was special is that they would stay open late. During the film festival, we [Roots] would throw these midnight spaghetti dinners that went on well into the night. That's something that started back in the Sisi era and that continued on at Sotto Sotto. It was just a great tradition.

Jimmy Molloy, luxury real estate agent

I grew up in that neighbourhood, so I remember when that space was a dry cleaner and after that it was a deli. I think it was closed down because they were running a bookie joint out of it. In the eighties it became Sisi Tratorria and then they ran into hard times and Marisa took it over. She really embraced what the space is – it's a basement. It's such an intimate womb-like space. It's a hidden gem, almost like a speakeasy quality. When you take your wife there it's like you're having dinner with your mistress. Today, there are so many restaurants in these huge spaces with these huge ceiling heights. They're like cathedrals, whereas Sotto Sotto was more like little chapel to get great pasta and grilled fish. You always feel better when you're under the covers – that's how you felt there. It was about intimacy and romance. I don't think you'd ever go there with your accountant.

Jason Priestley, actor

I was very sad to hear the news about Sotto Sotto, which I have certainly spent a lot of time in over the years. I started going in the mid-nineties, which was back when Beverly Hills 90210 was sort of at its height of popularity, and there weren't a lot of places I could go and just relax without getting approached by fans of the show. They really knew how to take care of people who were in the public eye and they had their cozy back corners where you could sort of hide away. I remember one really great night I had there was the night that my documentary, Barenaked in America, premiered at the film festival. We – myself and the Barenaked Ladies – did a big dinner there before we went to the Winter Garden Theatre. Another memorable night, I was there and I got to meet Steve Thomas, the hockey player. I ended up having dinner with him and his wife. For me, being a hockey fan, that was quite a thrill.

These interviews have been condensed and edited

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