The Drake, TO bastion of hipsterdom, adds a more worldly wing

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She has grown up!

The Drake Hotel — a reliable bastion of laid-back cool in this town — turned 18 last week. And to help her welcome her adulthood, I recorded myself. As someone who was at the opening of the Toronto game and has been watching its trajectory ever since, it was a chance to investigate some old ghosts but also check out the modern wing that just opened (a collection 32 additional rooms, with a sprawling rooftop suite that looks like a crash pad designed for Roger Sterling from “Mad Men”).

Pleasure? It started a little immediately when, after retrieving my key card, my eyes fell on an enclosed piece of paper answering key questions about the hotel. Besides things to know such as “What is the WI-FI code?” and “Where can I get ice cream?” there was this beauty: “Does this hotel belong to Drake?”

As if. There, in fine print, was the agreement: “No. We opened our doors in 2004, long before Drizzy helped put Toronto on the map.

“We get this question often,” the front desk clerk told me. Oh, honey, I thought: 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 a mash in the tradition of Toronto itself. First erected in 1890, the property was known as Small’s Hotel, its guests largely being passengers on the nearby Canadian Pacific Railway. In 1949, it was enlarged and renamed Drake, its fortune once again linked to the vagaries of the railway: when the neighborhood station closed, it too collapsed.

Eventually the space became a flophouse – characters straight out of “Les Miserables” floating through – and in the 1980s and 90s it served as both a punk bar and a rave venue. Entrepreneur Jeff Stober bought the place in 2001 (for a reported $860,000) and officially revamped it as Drake, a hotel and bastion of diverse art, culture and hipsterdom.

The opening night to usher in its new era, 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 range of media/film/music knowledge and some ‘costumes’ too, for good measure. It was a cold night. Queue to get in? Around the proverbial block.

To put it into perspective: the Drake 2.0 was born the same year the term “wardrobe malfunction” entered the common vernacular (that whole Janet Jackson Super Bowl thing); the Boston Sox won the World Series ending an 86-year drought (curses be damned); Paul Martin was the prime minister of this country (remember him?); “The Apprentice” premiered on TV (oh oh); and JLo and Ben Affleck spectacularly disengaged (during their first gun romance).

Putting it in other words JLo tells you exactly how much time has passed. The Drake is old enough now that he’s lasted a Lopez marriage (Marc Anthony, 2004 to 2014), a Lopez engagement (A-Rod, 2017 to 2021), an Affleck marriage (Jennifer Garner, 2005 to 2015) and, well , a Lopez-Affleck meeting (2021 to?).

A few days after the official opening of the Drake, I wrote: “It has only been open for a week and already the Queen Street West haunt seems to have always been there. That’s probably the biggest compliment I can give him. Neither It Spot nor Hot Spot, it seems, thankfully, to have transcended that terminally fatal designation.

Everyone came in those nascent years. I remember sitting next to Ryan Reynolds and Alanis Morissette one night in the dining room (remember when they were oddly engaged?). There was a post-party another night in the same space after the premiere of the movie “Hairspray,” during which young Zac Efron tiptoed around fame. From Sidney Crosby to Rachel McAdams, boldness flowed through the hotel. “A fireplace-smoking Keanu Reeves was found relaxing on the Drake’s patio the other day,” I remember writing.

An early fanfare for the Drake came inadvertently when his 30-year-old sous chef Alan Wyse began a May-December relationship with Kim Cattrall, then in the most vampy fervor of “Sex and the City.” It certainly caught the world’s attention. How’s that for hospitality?

There is also, of course, the Drake Underground, long an institution within an institution. A Valhalla sound that matches around 150, he’s seen acts ranging from Beck to MIA to Broken Social Scene; comedy nights and poetry slams, alike. In recent years, this is where Billie Eilish got her start in Toronto.

Planting myself in the new wing of the hotel for a night, I took a closer look at the new renovation: if the original wing is the youngest, what will be will be brother, the modern addition is the oldest , more worldly, always with one.

And what’s not to like about the rooftop suite, which features two en-suite bedrooms, a proper bar, a chic eight-seater dining table, and a sitting area? Think: modern Danish with witty pops of color and generous artistry. Everything from the lavishness of the door handles to the weight of the furniture told me the design had been very thought out. Did I mention the suite has a huge cocktail sized balcony? And that the whole lair seems made for post-pandemic madness… and just enough trouble?

Downstairs, the lobby also offers relief from 2022 with low-profile, low-profile seating, a few nooks designed for working, and an L-shaped corner bar that was fun to sit at. A small jewelry box, with only about six seats, is the coldest response to the hubbub next door. It makes for good one-on-ones.

Meeting Stober, the founder, the next morning when I was leaving, he told me he couldn’t believe it had been 18 years already. And that response, so far, has been good at limited expansion. “We’re all nostalgic, as you know,” he said, “but we also want to move on.”

Shinan Govani was a guest of the Drake Hotel, who did not review or approve this column.
Shinan Govani is a Toronto-based freelance columnist covering culture and society. Follow him on Twitter: @shinangovani

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