From Creepy Basement to Swanky Speakeasy

Catriona Smart grew up in Newmarket, Ontario, to a pair of bubbly parents who entertained constantly—and she caught the bug too. Smart, a former bartender and current creative agency founder, and her fiancé, Jimmy Cook, host all kinds of parties in her stone-faced 1920s mansion in Toronto’s Forest Hill neighbourhood, where she moved toward the end of 2016. 

Smart gutted nearly every part of the mansion before moving in—except for the 3,000-square-foot basement. A previous owner had transformed it into an ’80s-style grotto with a giant rectangular pool, built-in concrete daybeds and plenty of circular glass peepholes. “It was an engineering nightmare,” she says. “Our first expert told me that the grotto’s concrete slab and the water inside the pool were so heavy that without them, the house would collapse.” The space was mostly outfitted in grimy blue and white tile and was in no condition for use, but since Smart couldn’t get rid of it right away, she still had to pay for bi-weekly cleaning so the rest of the house wouldn’t smell like mildew and chlorine. At the time, her daughter Harlowe was only three years old, so the basement door remained locked for years. 

Finally, in early 2020, Smart found an engineer with a different opinion, who deemed a renovation possible as long as they underpinned the entire house beforehand—a process that took nearly five months. After the engineer removed the concrete slab underneath the grotto, they filled it in with dirt from the underpinning to provide the necessary weight to support the home. They worked with custom residential builder Carmelin Design Build on the rest of the house, who added some more structural beams to the space.

Smart and Cook knew they wanted to create an entertaining haven but waffled over exactly what it should look like—until everything shut down during the pandemic. They couldn’t go out to dinner anymore, so they hatched a plan to create their own speakeasy bar where friends could gather and feel like they were in an upscale restaurant or lounge. “We wanted to create a fun space where people could forget about their worries during COVID,” Smart says. “And now we have a club in our basement.”

Her vision drew on old Hollywood and vintage Floridian influences. The stairs lead down into an all-pink entryway, with a trough-style onyx sink that sits opposite a series of three private bathroom stalls and a shower. This area can be entirely closed off from the rest of the bar with a disguised sliding door, evoking the feel of a secret underground club. “If you don’t know, you wouldn’t think there’s anything else down there,” she says. There’s an entrance to the basement from the backyard, too, which comes in handy when her now-11-year-old daughter has friends over for pool parties. 

Past the entryway is an expansive room centred around a 21-foot statement bar, made from jade with hints of amber and inlaid with LED lights. Some curvy light-pink sofas, recessed daybeds, a DJ booth, bookshelf display and heaps of moody lighting complete the club-like feel. When Smart and Cook host dinner parties instead of dance parties, they simply move the sofas out of the way and cover a series of folding tables in linens. 

Smart worked as a bartender for a few years while attending the University of Toronto, so she needed the bar to be optimally functional as well as aesthetically stunning. It’s outfitted with a sink, two fridges and an ice machine—and it’s always stocked with their favourite tequila, Don Julio 1942. Backed by a vintage-looking mirror overlaid with a giant Art Deco–like sun that lights up, the bar easily looks the part of a glam ’60s jazz club. Smart was inspired by many of the bars and restaurants she’s been to around the world, like the private club Annabel’s in London and the Las Vegas restaurant and lounge Delilah. “I don’t go out to clubs often anymore, but I’ll have a Whitney Houston singalong down here any day,” she says. 

She knew the space was destined for rowdy, shoes-on dance parties, so durability was crucial. The floors are a gray tile that was shaped and placed to look like herringbone wood. The rose-hued sofas are upholstered in a faux suede that’s covered in a 3M product. “Someone spilled an entire glass of red wine on one, and it just trickled off,” she says.

One of her favourite basement nights was an impromptu Caribana bash when they had 150 people dancing and singing to ’80s and ’90s music all evening long. “It was one of those magical nights where you don’t plan anything and all of a sudden everyone is here,” she says. Unfortunately, that night someone stepped on one of her colourful coffee tables—sought-after “Candy Cubes” designed by Dutch artist Sabine Marcelis—and fell right through. Drake even spent a few fun nights in the basement himself and eventually named the song “Jimmy Cooks”—a track from his 2022 album Honestly, Nevermind with more than 900 million streams on Spotify—after Smart’s fun-loving fiancé. 

Since it was finished in the fall of 2022, Smart estimates they use the basement for a special event at least once a month. In addition to large holiday potlucks and more intimate family affairs, they’ve also had well-known chefs like Bar Prima’s Craig Harding come in for charity dinners and hosted evenings for clients like celebrity makeup artist Sir John. She also runs a supper series called “Guess Who’s Coming to Dinner?” where she, Cook and the team at her company That Good Co. all invite acquaintances from various industries to network. Her favourite part of the space is how everyone puts their phones away and disconnects from reality for a while. 

Smart and Cook also use the basement as a private hair salon: because they couldn’t get their hair done anywhere during COVID, they added a mini salon in a former storage room, which they still use today to get their hair cut.