This week in Toronto culture: Clairo, Cyndi Lauper’s farewell tour, Bob the Drag Queen and more

Yes, it’s getting chilly out there, but you won’t want to miss our picks for the best culture events in Toronto this week. Resist the allure of the couch and read on for our recommendations.
Oct. 19 at Canadian Music Centre
If you love the idea of horror films but can’t handle the jump scares, this operetta is for you. Songwriter and comedian Eli Pasic is the mastermind behind this one-man musical comedy, a tongue-in-cheek variation of the 1970s horror classic.
Oct. 20 at Scotiabank Arena; Oct. 21 at Phoenix Concert Theatre
Just wanna have fun? Grab a ticket to see Cyndi Lauper’s farewell tour. After her big arena show on Sunday, Lauper will appear at the Phoenix to participate in an intimate conversation for the podcast “Behind the Vinyl.” Doors open there at 12:30 p.m.
Oct. 22 at History 
The Grammy-winning American singer-songwriter is bringing her Purple Skies tour to the east end concert venue, quite a step up from her previous Toronto gig at the Axis Club in September 2023.
Dance-pop singer Maisy Kay opens the show. 
Oct. 24 at Paradise Theatre
For those looking to get into the Halloween spirit, consider checking out “The Babadook,” the 2014 Australian psychological horror film whose central figure unexpectedly became a queer icon.
The Paradise screening will be co-presented by Queer Cinema Club and MUBI. Tickets come with a drink voucher and complimentary popcorn. Come dressed as your interpretation of “maternal horror” for a chance to win a prize.
Oct. 23, Oct. 24 and Oct. 25 at Massey Hall
Get ready to be charmed as indie-pop singer-songwriter Clairo arrives in Toronto for three shows. South African singer-songwriter Alice Phoebe Lou joins Clairo on all stops of the 25-city North American tour. 
One dollar from each ticket will be donated to support women’s reproductive rights.
Oct. 22 to Oct. 26 at the Theatre Centre
More than 50 performers, including Toronto’s own Andrew Phung, Tim Blair and Small Friend Tall Friend, will appear in nine shows over five nights for the fifth annual festival. It’s intended for those 18 years and older and features programming between 7:30 p.m. and 9:30 p.m. — an event, organizers say, that “respects your bedtime.” 
Tickets are $20 and can be purchased at the Theatre Centre’s website.
Through Oct. 27 at Buddies in Bad Times Theatre
Star theatre critic Joshua Chong recommends checking out ”The Noose,” which tells the story of two Haitian immigrants, a middle-class intellectual and a peasant, who clash, banter and ultimately unite in a New York City basement apartment in the 1980s. There’s also ”Gemini,” a two-hander that tells the story of a bartender and one of her regulars, which is described as “part fairy tale, part cautionary tale.”
Tickets are available at fringetoronto.com.
Oct. 23 and Oct. 24 at Queen Elizabeth Theatre
Fresh off his opening slot on Madonna’s recent tour, the “RuPaul’s Drag Race” winner brings his own first headlining world tour to Toronto.
Described as “more than just a comedy show,” the 18-plus event will display his “unparalleled ability to blend stand up comedy, crowd work, and music, all while entertaining his audience with the charisma and flair he is renowned for.” 
More information can be found on the Queen Elizabeth Theatre’s event page.
Oct. 25 and Oct. 26 at Imagine Cinemas Carlton
The 19th annual Macedonian Film Festival, which aims to broaden the awareness of Canadians “to Macedonian talent and culture as well as focus attention on contemporary and historical issues facing the Macedonian diaspora,” will showcase movies made by Macedonian directors, writers and producers from all over the globe. 
Tickets can be purchased at macedonianfilmfestival.com.
Brimming with big hooks and even bigger emotions, indie-pop singer T. Thomason’s album “Tenderness,” arriving Oct. 25, is an immersive dive into themes of self-determination, independence and queer/trans joy.
On Oct. 24, T. will be hosting an listening party at Lost Tonic in Toronto. (Tickets are available at sidedooraccess.com.)
We asked T. to share some of his favourite spots in Toronto, plus a few things he’s into right now.
Q: What are three things you’ll always do and places you’ll always go during a free weekend in Toronto?
A: I love a weekend in Toronto because I usually do a “screen-free” Saturday, and it allows me to explore the city and really connect with it and discover new places. I will always take my dog on a walk to Christie Pits or Bickford, grab a chai latte at Emily Rose Cafe, and explore some of the used bookstores in the Annex.
Q: Your music can be described as indie pop, with a focus on queer/trans joy and liberation. Where does this scene live in the city?
A: I think this scene lives wherever it’s able to pop up. Queer events like Big Gay Night, bars like Three Dollar Bill. But honestly, the queers are everywhere.
Q: What’s your favourite venue to perform in and to see live music?
A: I love seeing music at the Burdock Music Hall because the sound is always amazing and it’s such an intimate experience with the artist. I love performing at the Baby G. Some of my favourite headlining TO shows have been there and so it’s full of great memories for me.
Q: What concerts or shows are you most excited to see this fall?
A: I’m going to see Maggie Rogers on the 22nd and I’m so excited for that.
Q: What are you reading right now?
A: I’m currently reading “Run Towards the Danger” by Sarah Polley.
Q: What’s the last movie you saw that you’d recommend?
A: I saw “Fanatical: The Catfishing of Tegan and Sara” at TIFF and it was crazy! Highly recommended for queers, T&S fans, and true crime lovers across the board. If you’re all three like me, even better.
Q: What are you streaming right now?
A: I’m binge-listening to the “Otherworld” podcast right now, and I’m trying not to start a (TV) show because I have no self control, but the last thing I got into was “Industry.”
Q: Who is one under-the-radar Toronto artist more people should know about?
A: R. Flex. Don’t sleep. They are friggin’ incredible.
Here are a few things the Star’s Richie Assaly is into this week:
The hip hop community is in mourning this week, following the sudden, unexpected death of Kaseem Ryan, better known as Ka, a beloved underground rapper from Brownsville, Brooklyn. Known for his sparse beats and proudly uncommercial approach, Ka — who also had a long career as a firefighter — was a rare example of a rapper who found success in his middle age. Indeed, though he was a prolific artist throughout his career, it was his output in the 2020s that finally earned him a degree of commercial fame and critical acclaim.
If you haven’t listened to Ka before, dive right in with “The Thief Next to Jesus,” his final album, which was released in August. My personal favourite is “Descendants of Cain” from 2020, an album that closes with “I Love (Mimi, Moms, Kevs),” a stunning track dedicated to Ka’s wife, mother and a departed friend.
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Nearly a year after Pitchfork was hit by mass layoffs and folded into GQ, five Pitchfork alum have launched Hearing Things, a new music publication. The site, according to a New York Times profile, “aims to capture the original independent spirit of Pitchfork while tuning out the stan armies that worship huge artists.”
“The search-engine-based model changed the incentive to write about the Taylor Swifts of the world, and it made the internet a worse place,” said Jill Mapes, one of the founders. “One thing that I learned at Pitchfork is it is very hard to get people to click on a headline about an artist that they don’t know. Why can’t you create an environment where people are primed for that because that’s what they want?”
The site, which features reviews, artist profiles and blog-style musings on music, launched with “100 Songs That Define Our Decade So Far,” an unranked list that introduces readers to the editors’ taste, while also framing the site as an alternative to Pitchfork, which released a similar list earlier this month.