Lilly Singh went from filming YouTube sketches in her Scarborough bedroom to becoming one of Canada’s most recognizable TV hosts. Best known as “Superwoman” in her early days, she’s now leading the charge on Battle of the Generations, CTV’s trivia show. We caught up with Singh to talk about her rise.

What surprised you the most about the new season?

I would say that at least once an episode a boomer will say something where I’m like, “I did not expect that.” The boomers, for sure, are just, you can’t see it coming. I could never anticipate what’s going to happen with a boomer. 

What makes ‘Battle of the Generations’ so special for you?

What makes it special for me is that every time I do a project I think, could I watch this with my parents? Could I get a bunch of friends together, watch this and have fun? Because I do feel like, in today’s day and age, we’re very divided when we watch things. We’re all just siloed in our own spaces. What’s so special about game shows like this is the magic of gathering with your family and playing along together. That’s really special to me, and that’s why I gravitated toward it. 

How do you keep that host energy fresh?

Well, here’s the thing about me, Ron, I have a lot of energy almost all the time. Anyone I know would describe me as a very energetic person. But specifically for this, another key difference this season is that we have a live audience. I love nothing more than playing off a live audience. The contestants are so fun as well.

How do you think you’d stack up if you were one of the competitors on ‘Battle of the Generations’?

Honestly I would probably do quite horribly. Don’t get me wrong, I’m good with internet, culture, music, but for Gen X and Boomer, I just would know nothing. I truly would know nothing. Sometimes when these contestants know the answers to things, I’m like, I don’t even understand how you know this.

Now for some short answer questions. To begin, what was your first job?

I worked at Harvey’s on Morningside.

Worst piece of career advice?

I was walking late to set one day, and I was really stressed about being late, and someone looked at me and said, “It’s OK, you can be late. You’re the talent.” And I said, “I need to never listen to you.”

How do you get away from it all?

I love nothing more than going to a movie theatre. I go by myself quite often.

What is your greatest fear?

Oh, my greatest fear is I’ll give you a stupid one and a deep one. A stupid one is spiders. I can’t. I do not mess with spiders. But a more deep one is just to be stagnant and bored. I want to be moving and doing things and being excited about life.

What is your greatest extravagance?

My events. If I wasn’t an entertainer, I would be an event planner. I mean, you need to see me make a charcuterie board. It’s a spiritual experience, honestly.

Where is the first place you send visitors in Toronto?

You’re gonna judge me. I’m gonna tell you a restaurant, my favourite restaurant, and it’s just so nostalgic for me. I just love Swiss Chalet. It just tastes like my childhood. 

What talent would you most like to have?

I wouldn’t love to play an instrument, and I would love to play the electric guitar. I think that’s so cool. 

What is your most treasured possession?

So I only sleep on exactly one pillow in my life, no matter where I am in the world. I take a therapeutic neck pillow that my mom made  a pillowcase for. It’s a travel pillow. I’m literally against it right now. That is my most prized possession because if I ever lost it I would not be able to sleep on any other pillow.

What is your personal motto?

Work hard and be nice to people. 

When two major talents come together, conversations get real. Jenna Ortega and Scarborough-born global sensation The Weeknd recently sat down for Complex’s “The Best & Worst Things Ever (GOAT Talk)” segment and revealed their picks for the greatest Canadian of all time. Spoiler: it might not be who you’re expecting.

When it came time to name their GOAT Canadians, fans might have been expecting the usual suspects — hockey legends, music icons, or political figures. But The Weeknd, whose real name is Abel Makkonen Tesfaye, surprised everyone with a shout-out to a very different kind of Canadian icon.

“The Trailer Park Boys,” he said, referring to Canada’s most beloved fictional gang from a small town in Nova Scotia. “I like Bubbles,” he added, nodding to the character known for his thick-lensed glasses, played by Mike Smith.

Ortega responded that her GOAT Canadian is Canadian filmmaker Denis Villeneuve, who hails from Montreal (he’s most known for directing the Dune flicks). Last year, Ortega revealed to BuzzFeed Celeb that she had auditioned for Dune when she was 15, but Zendaya ended up with the role.

 

View this post on Instagram

 

A post shared by Toronto Rapstars | Hip-Hop Media & Events (@torontorapstarss)

The two actors are promoting their musical drama, Hurry Up Tomorrow, about a musician plagued with insomnia (Tesfaye) and his encounter with a mysterious stranger (Ortega), and their fans were all here for the GOAT debate!

One commenter joked, “Wednesday interviewing the weeknd probably went over a lot of heads”, referencing Ortega’s role as Wednesday Adams on Netflix’s ultra-popular Addams Family spin-off, Wednesday.

Others were surprised that The Weeknd didn’t choose fellow Toronto musician Drake, who’s currently working on his next solo album. Back in the day, Tesfaye publicly thanked the rapper for helping to launch his career.

“I will always be thankful — if it wasn’t for the light he shined on me, who knows where I’d be. And everything happens for a reason,” The Weeknd told Rolling Stone in a 2015 interview. “You never know what I would say if this success wasn’t in front of me now.”

Others thought there were better GOAT options. “Céline Dion Wayne Gretzky Shania Twain all would’ve been super answers” one user said, while others thought that the Trailer Park Boys was the perfect response.

“The fact he said trailer park boys actually makes him real af hahah” another user said.

You can watch their full GOAT interview here.

Nestled in the middle of Toronto’s Church Wellesley Village is a piece of history — Glad Day Bookshop, the oldest surviving queer bookstore in the world. But now the neighbourhood fixture is making a major change, moving from its home in the Village to a new Queen West storefront.

In 2024, Glad Day posted a call to action, asking for support to save the bookstore from eviction and sharing that the shop had been going into debt for two years and often short on rent. The subsequent fundraising campaign helped the business stay afloat for the time being, raising $200,000 of the $300,000 goal — set with the intention of “avoid[ing] shutting down and giv[ing them] one more year to find creative ways of surviving.”

The bookstore has done just that. “This funding gave us time to find this practical solution that reduces our facility costs by 95% while we continue to explore long-term spaces and creative strategies,” an Instagram post sharing the news read.

The practical solution is a short-term location on Lisgar Street, a brand new space that will feature a small bookstore, cafe counter, event space, communal lounge and park out front. While the facility costs will intentionally be very low for this space, revenue may be low as well — the current Glad Day Bookshop not only operates as a bookstore, but as a cafe by day and bar by night, running drag brunches, queer social events and more in the space. Without the ability to replicate the entire current business model, most crucially, alcoholic drinks, revenue likely won’t reflect current targets.

In order to make the transition to the new space, Glad Day is fundraising again, this time with a goal of $150,000. The target includes $30,000 to pay authors and artists for event programming, $25,000 to design and outfit the new space, $25,000 for six months of operating costs, $25,000 for moving and storage and $30,000 to revitalize the books and art selection.

Crucially, the target also includes $15,000 to help Glad Day continue on Church Street for a final two months — specifically for the month of Pride.

Originally launched in 1970 by gay activist Jearld Moldenhauer to help build the city’s gay rights movements, Glad Day Bookshop grew from selling books out of a backpack to one of the largest queer bookstores in the world. The shop moved from place to place throughout the city over the years, settling at Yonge and Wellesley in 1981 before eventually moving to its current home at 499 Church St.

Glad Day noted that ideally, this short-term space won’t be forever. “We are working with the City of Toronto on finding a sustainable ‘forever home’ in the Village area in the future,” the team wrote. 

It looks like there’s some work going on behind the scenes to make this happen — Chris Moise, the city councillor for Toronto Centre, wrote about the move on Instagram, stating: “I have been working behind the scenes with City Staff and a group of community leaders to secure a new community space in The Village and look forward to welcoming Glad Day back shortly. Stay tuned for updates this summer.”

Torontonians will have the chance to strip down and participate in the 21st iteration of the clothing-optional World Naked Bike Ride (WNBR) at Coronation Park on June 14. The annual event originated in Vancouver in 2004, but now takes place in 80 cities across the globe.

The ride is meant to celebrate cycling and the human body, as it demonstrates the vulnerability of cyclists on the road. It also represents a protest against the over-consumption of oil. “Less Gas, More Ass,” the organizers have stated.

Participants are encouraged to wear as little as they can while still feeling comfortable about it — that includes everything from birthday suits to bathing suits!

“People of all ages, sizes, builds and appearances ride on World Naked Bike Ride. At the ride, you’ll be treated with dignity and respect no matter what your body looks like,” the organizers state on their website.

The ride will begin at 1 p.m. at Coronation Park, by the waterfront at the centre of the park, and end at 5 p.m. Participation is completely free and requires no registration, but it’s recommended cyclists arrive an hour before start time. While the ride is legal, participants are encouraged to bring clothes with them and get dressed at the end of the ride to avoid any conflict with law enforcement.

If you’re not comfortable participating in the event, you can spot the riders as they pass through Kensington Market, Yorkville, Sankofa Square (formerly Yonge-Dundas Square) and the CN Tower. Sugar Beach will be a hydration stop, and Trinity Bellwoods Park will have a washroom and hydration stop.

For those who are wondering if it’s uncomfortable to ride naked, organizers have stated that, surprisingly, for all genders, riding naked isn’t especially less comfortable than riding clothed.

“When riding with clothes on you’re often rubbing against the seams, so in some ways naked riding is comfier! Ride routes will often be chosen with less experienced cyclists in mind, so will avoid hills and be more leisurely in pace, increasing comfort,” the organizers state.

For those who don’t have a bike, any sort of skates (skateboards, inline skates, roller skates, rollerblades, etc.) are also welcome.

“Walking isn’t encouraged since walkers won’t be able to keep up with rides travelling on foot, but any alternate body-powered transport is welcome and encouraged,” the organizers state, adding that the only way participants might get hurt is if they don’t wear any sunscreen or if they fall off their bikes.

“Your bottom will probably not hurt any more than when you ride with your clothes on. If you get sore (with or without clothes), it could be that you have the wrong shape of saddle. Aside from getting a saddle that fits you better, you could get a padded bike seat, or gel sadle-cover,” organizers stated. “If you haven’t been on a bike for years, your bottom may feel sore after the first few rides, so you might want to get in practice by cycling more often before the WNBR day.”