Checking in with a modern-day Drake
She’s all grown up!
The Drake Hotel — a reliable bastion of laid-back cool in this town — turned 18 this past week. And to help welcome her adulthood, I checked in. As someone who was at the opening of the Toronto fixture, and has been watching its trajectory since, it was a chance to survey some old ghosts but also vet the just opened Modern Wing (a collection of 32 added rooms, complete with sprawling rooftop suite that looks like a crash pad made for Roger Sterling from “Mad Men”).
The fun? It got going kind of immediately when, upon collecting my key card, my eyes roved to an attached piece of paper answering key questions about the hotel. Besides such gotta-knows as, “What’s the Wi-Fi code?” and “Where can I get ice?” there was this beauty: “Is this hotel owned by Drake?”
As if. There, in fine print, was the deal: “No. We opened our doors in 2004 — long before Drizzy helped put Toronto on the map.”
“We get that question a lot,” the employee at the reception desk told me. Oh, honey, I thought-bubbled: Drake was still in a wheelchair earning his chops on “Degrassi” when this place opened on a barren stretch of Queen West, past Dovercourt.
The long history of the Drake is one puréed into the lore of Toronto itself. First erected in 1890, the property was known as Small’s Hotel, its patrons largely consisting of passengers of the nearby Canadian Pacific Railway. In 1949, it was expanded and rechristened as the Drake, its fortunes once again tied to the vagaries of the railway: when the neighbourhood station closed, it too flailed.
Eventually, the space became a flophouse — characters right out of “Les Misérables” floating through — and through the 1980s and ’90s, it served as both punk bar and rave venue. Entrepreneur Jeff Stober bought the place in 2001 (for a reported $860,000) and officially refashioned it back into the Drake, a hotel doubling as a bastion of art, culture and miscellaneous hipsterdom.
The opening party to usher in its new era, on Valentine’s Day 2004, I remember well: much of the downtown who’s who in the house. Many of them with their Razr flip phones and in their True Religion jeans. A good array of the media/film/music cognoscenti and a few “suits,” too, for good measure. It was a cold night. The line to get in? Around the proverbial block.
To put it in perspective: the Drake 2.0 was born in the same year that the term “wardrobe malfunction” entered the common vernacular (that whole Janet Jackson thing at the Super Bowl); the Boston Sox nabbed the World Series ending an 86-year-old drought (curses be damned); Paul Martin was this country’s prime minister (remember him?); “The Apprentice” first premiered on television (oh oh); and JLo and Ben Affleck spectacularly disengaged (during their first, guns-ablaze romance).
Putting it in further JLo terms tells you exactly how much time has lapsed. The Drake is old enough now that it has spanned one Lopez marriage (Marc Anthony, 2004 to 2014), one Lopez engagement (ARod, 2017 to 2021), one Affleck marriage (Jennifer Garner, 2005 to 2015) and, well, one Lopez-Affleck reunion (2021 to ?).
Days after the Drake’s official opening, I columnized: “It’s been open for only a week and already the Queen Street West hangout seems as if it’s always been there. That’s probably the highest compliment I can pay it. Neither It Spot nor Hot Spot, it seems, happily, to have transcended that terminally fatal designation.”
Everyone came in those nascent years. I remember sitting near Ryan Reynolds and Alanis Morissette one night in the dining room (remember when they were bizarrely engaged?). There was a post-party another night in the same space following the premiere of the movie “Hairspray,” at which young Zac Efron made the rounds on the tippy toe of stardom. From Sidney Crosby to Rachel McAdams, the boldface flowed at the hotel. “A chimney-smoking Keanu Reeves was found chilling on the patio of the Drake the other day,” I recall writing.
Some early fanfare for the Drake came inadvertently when its 30year-old sous-chef, Alan Wyse, began a May-December relationship with Kim Cattrall, then in the vampiest fervour of “Sex and the City.” That certainly got worldwide attention. How’s that for hospitality?
There is, of course, the Drake Underground, too, long an institution within an institution. A sound Valhalla that fits about 150, it has seen acts ranging from Beck to M.I.A. to Broken Social Scene; comedy nights and poetry slams, alike. In more recent years, it was where Billie Eilish made her Toronto debut.
Planting myself in the new wing of the hotel for a night, I got a closer look at the new reno: if the original wing is the younger, que sera sera sibling, the modern addition is the older, more worldly, still with-it one.
And what was not to like about the rooftop suite, which comes with two ensuite bedrooms, a proper bar, posh eight-seat dining table plus sitting area? Think: Danish Modern with witty pops of colour and generous art. Everything from the sumptuousness of the door handles to the heft of the furniture told me the design has been very thought out. Did I mention the suite has a massive, cocktail-partysized balcony? And that the whole lair seems made for post-pandemic splurge … and just the right amount of trouble?
Downstairs, the lobby, too, offers some 2022 relief with its discreet, low-sunken seating, a few nooks designed for working and an Lshaped corner bar that was fun to sit at. A tiny jewel box, with just six or so seats, it is the more chill answer to the hubbub next door. It gives good tête-à-tête.
Running into Stober, the founder, the next morning when I was checking out, he told me he could not believe it had already been 18 years. And that the response, so far, has been good to the limited expansion. “We are all about nostalgia, as you know,” he said, “but we are also about moving forward.”
We are all about nostalgia, as you know, but we are also about moving forward.
JEFF STOBER, WHO BOUGHT THE DRAKE HOTEL IN 2001