25 wild, brilliant and tragic events from the past 25 years that defined culture in Toronto

2024

Taylor Swift takes over Toronto 

For two magical weeks in November, Taylor Swift cast a spell over Toronto. Thousands of Swifties from around the world made the pilgrimage to experience the pop superstar’s penultimate stop of her record-breaking Eras Tour. Bedazzled in sparkles and sequins, they flooded our streets, restaurants and bars, turning Toronto into Taylor’s Town. Inside the Rogers Centre, the pop icon performed a marathon three-and-a-half hour set, playing through the most popular hits of her career. Those six concerts, months in the making, marked not only one of the largest cultural events of the century, but also in the city’s history. — Joshua Chong

2023

Toronto tests out booze in parks 

Though it was technically illegal at the time, many Torontonians drank and socialized in parks with friends during the COVID-19 pandemic due to restrictions on indoor social gatherings. In the summer of 2023, Toronto finally tested a pilot program that officially allowed residents to crack open a cold one at certain parks across the city. Despite initial concerns that the initiative would lead to increased public disobedience and littering, the program was overwhelmingly well-received and was adopted permanently the following year. — Joshua Chong 

2022

NOW Magazine ends as we know it

NOW Magazine’s newsstands were once ubiquitous in Toronto. Launched in 1981 by Michael Hollett and Alice Klein, the free, alt-weekly publication had a circulation of more than 60,000 copies at its peak. It was especially known for its progressive politics and near-exhaustive coverage of the city’s indie arts scene. But the media organization long struggled with a decline in advertising revenue — a decline, some say, that echoes the struggles of Toronto’s arts industry as a whole. Since 2019, the paper has changed ownership twice and currently operates as a digital-only publication. But with its former staff entirely gone, NOW is largely a shell of its former self. — Joshua Chong

2021 

Ford announces controversial Ontario Place redevelopment

Premier Doug Ford was met with controversy when he announced plans to redevelop Ontario Place, once a booming cultural hub and urban park on Toronto’s waterfront that’s been closed since 2012 due to mounting financial losses. The provincial government’s proposal included the preservation of Ontario Place’s Cinesphere and iconic pods, along with the construction of a private spa, to be operated by the Austrian company Therme, and the relocation of the Ontario Science Centre to the site. Ford’s government initially pegged the project to cost as little as $335 million, but that figure has since ballooned to more than $2.2 billion. In 2024, the province’s auditor general went on to lambast the redevelopment scheme, saying it was “not fair, transparent or accountable.” — Joshua Chong

2020

The COVID-19 pandemic brings the curtain down

No single event has had more of a lasting impact on the city’s cultural sector than the COVID-19 pandemic. Over a single week in mid-March, nearly every arts organization in the city was forced to close its doors, as the number of confirmed COVID-19 cases and deaths exponentially climbed. What was initially intended to be a closure of several weeks turned into a months-long lockdown, followed by the easing of restrictions in fits and starts. Many companies that closed their doors in 2020 never reopened. Those that did faced a long road to recovery amid changing consumer habits and declining revenue streams. — Joshua Chong

2019 

Toronto basks in the glory of the Raptors championship

Few Torontonians — in fact, few Canadians — will ever forget where they were on June 13, 2019, when the scrappy Raptors, led by a truly superhuman effort from star Kawhi Leonard, defeated the juggernaut Golden State Warriors to win their first NBA Championship. As the final buzzer sounded, the city erupted into a cacophony of cheers, blaring horns and screams of delight, as thousands poured into the streets to celebrate what felt like, at least for embattled Toronto sports fans, the fulfilment of destiny. Of course, the celebrations didn’t stop that evening, but continued for several delirious days, culminating in a victory parade that drew an estimated two million fans into the city streets to catch a glimpse of the hometown heroes. Taking place just months before COVID-19 forced the city and much of the world to shut down, the championship spring was a special and rare moment of collective joy and triumph for a city that is too often hindered by cynicism or impostor syndrome. For a few jubilant weeks, as the warm spring turned to another hot summer, it felt like there was no better place on earth to be. — Richie Assaly

2018

Theatre company shaken by sexual assault allegations

Soulpepper, one of the most prominent not-for-profit theatres in Toronto, was shaken by a series of sexual assault and harassment allegations levelled against Albert Schultz, its co-founder and artistic director. Four female actors each filed separate civil claims in early January, seeking $4.25 million from Soulpepper and $3.6 million from Schultz for what they described as a pattern of sexual harassment. Schultz resigned two days after the lawsuits were filed and the case was settled by the end of the summer. But it resulted in a broader, years-long reckoning and cultural renewal at Soulpepper, ultimately leading to the appointment of Weyni Mengesha as its artistic director. — Joshua Chong

2017

A new era for Canadian musical theatre

When “Come From Away” officially opened on Broadway in 2017, it ushered in a new, golden age of Canadian musical theatre. It’s easy to forget that David Hein and Irene Sankoff’s stirring masterpiece, which ran in New York City for five years and spawned countless productions around the globe, was developed out of a Sheridan College classroom in Oakville, Ont., and funded, in part, by a government arts grant that allowed the married writing team to travel to Newfoundland on the 10th anniversary of the Sept. 11 terrorist attacks. “Come From Away” may be the most successful musical in this country’s history but, more than that, it should also be remembered for paving a path for emerging writers in this country, helping establish a developmental pipeline for new works and pushing playwrights to dream even bigger. — Joshua Chong

2016 

“Kim’s Convenience” jumps from stage to screen

Canadians hadn’t seen a TV family like the Kims before when “Kim’s Convenience” premiered in October 2016. Spun off from Ins Choi’s hit play, the sitcom featured Korean Canadian actors (Paul Sun-Hyung Lee and Jean Yoon) playing Korean immigrants who run a Toronto convenience store, fending in comic ways with their Canadianized children and the larger community. It wasn’t devoid of stereotypes and we now know about the lack of diversity behind the scenes, as flagged by star Simu Liu and others, but it was beloved not only by viewers here but millions worldwide after Netflix picked it up. The recent cancellations of Canadian TV comedies with diverse characters make it feel like “Kim’s” was perhaps more an outlier than a vanguard, but it still had value to those who hadn’t seen themselves on homegrown TV before. As Liu said in a 2021 interview, it was important for “Canadians that quite honestly have not seen themselves onscreen … to know that you are a part of the fabric of Canadian society and culture and identity.” — Debra Yeo

2015 

“Schitt’s Creek” begins journey to worldwide acclaim

When it debuted in January 2015, there was a lot riding on “Schitt’s Creek.” National broadcaster CBC was in desperate need of a hit; and having “SCTV” legends Eugene Levy and Catherine O’Hara in the cast meant higher expectations than for your garden variety sitcom. Although we couldn’t have known then what a sensation “Schitt’s” would become — migrating first to Pop TV in the U.S. and then Netflix on its way to a record Emmy Awards haul in 2020 — the makings of its greatness were present in that first season. This Ontario-made show about a spoiled rich family who loses everything, but finds themselves in the process, was the first of several TV series that brought Canada international acclaim. — Debra Yeo

2014

Jian Ghomeshi allegations spark a national discourse

In the fall of 2014, Canada’s public broadcaster fired its star radio host, Jian Ghomeshi, in the wake of a series of sexual assault and harassment allegations. Reporting by the Star revealed that three young women, all about 20 years his junior, alleged that Ghomeshi was physically violent with them without their consent during sexual encounters or in the lead-up to sexual encounters. Ghomeshi was charged with four counts of sexual assault and one count of overcoming resistance by choking. In 2015, he faced an additional three charges of sexual assault. And though he was never convicted of sexual assault, the disturbing allegations against one of Canada’s best known media personalities sent shock waves through the country, and sparked a national discussion about sexual assault and the cult of personality nearly three years before the #MeToo movement grew to prominence in Hollywood and beyond. — Richie Assaly

2013

NXNE music and arts festival soars to new heights

Writing in 2025, it’s hard to imagine a world where you might be able to see some of your favourite artists perform live without spending hours on Ticketmaster or forking over a small fortune. But what sounds like a luxury was actually the norm during the early 2010s heyday of North by Northeast (NXNE) — an annual music and arts festival founded in 1995 that curates live music in independent venues across the city — when Yonge-Dundas Square in downtown Toronto was transformed into a massive concert venue hosting dozens of shows from local and international artists. In the summer of 2013, throngs of Toronto music fans jammed into the square to check out free shows from the National, Billy Talent, Social Distortion and Ludacris. It was also the year that NXNE expanded its scope beyond music, film and interactive installation, adding comedy and art showcases across the city. NXNE remains a vital Toronto arts institution today, but cash-strapped music fans will be forgiven for pining for the outdoor mayhem of yesteryear. — Richie Assaly

2012 

A year of growth for Toronto’s cultural festivals

The year 2012 was a big one for big arts festivals in Toronto. Hot Docs bought the shuttered Bloor Cinema and turned it into the Bloor Hot Docs Cinema, making it their official home base. It was also the year that Just for Laughs launched a Toronto version of its legendary comedy festival — originally dubbed JFL42 — hosting hundreds of the industry’s best comics. Both Hot Docs and JFL42, now Just for Laughs Toronto, survived the pandemic but, 12 years later, their destinies remained strangely twinned and slightly precarious: in 2024, the Hot Docs theatre shuttered for months to recoup costs, while JFL skipped its 2024 fest altogether after losing a huge pile of cash (in an email scam, of all things). — Briony Smith

2011

Drake’s OVO Fest spotlights burgeoning music scene

The inaugural OVO Fest was in 2010, but it was the 2011 edition of the annual summer music festival that acted as both a showcase of Toronto’s exploding R&B and hip-hop scene, and a chance for Drake to flex his rapidly rising cultural cachet. Held at the Molson Amphitheatre (today known as the Budweiser Stage) just a few months before the release of Drake’s seminal sophomore album “Take Care,” the single-day extravaganza featured an extraordinary cohort of surprise guests, including hip-hop luminaries Lil Wayne, Nas, Rick Ross and J. Cole, plus a surprise 30-minute set from the legendary Stevie Wonder. But looking back, perhaps the most significant moment of the event took place earlier in the evening, when the Weeknd took the stage for one of his very first live performances. Who could have predicted that this mysterious singer from Scarborough, whose moody and atmospheric approach to R&B had lit the internet on fire earlier in the year with the release of the “House of Balloons” mixtape, would within years transform into a Super Bowl-calibre megastar? The 2011 edition of OVO Fest not only put Toronto’s music scene on the map, it established Drake as one of pop culture’s premiere tastemakers. — Richie Assaly

2010

Toronto International Film Festival finds its new home

At the start of the 2010 Toronto International Film Festival, the arts organization inaugurated its new home, the Lightbox, with a block party that shut down King Street West and drew about 1,000 revellers to the entertainment district. Seven years in the making, the venue replaced TIFF’s old digs at the Art Gallery of Ontario and now hosts the company’s year-round programming. Located in the five-level podium of a 46-storey residential tower, the state-of-the-art development features five cinemas, gallery spaces and two restaurants. — Joshua Chong

2009 

Toronto theatre titan convicted of fraud and forgery

Garth Drabinsky was one of the theatre industry’s most prominent producers in the 1990s. His company, Livent, was behind the long-running Canadian production of “Phantom of the Opera,” and also helped usher musicals such as “Ragtime” and “Kiss of the Spider Woman” to Broadway. But by the turn of the century, Drabinsky’s business began to unravel as he fought criminal charges in both Canada and the U.S. Drabinsky and his business partner, Myron Gottlieb, were ultimately convicted of fraud and forgery in 2009 in Toronto, marking the end of the decade-long saga and indelibly changing the face of commercial theatre in the city. — Joshua Chong

2008

The AGO unveils Frank Gehry-designed wing

When work began on the Art Gallery of Ontario’s $276-million renovation in 2004, expectations were high. The man tapped to lead the project was none other than Frank Gehry, the renowned Canadian-American architect who grew up not far from the museum. It also marked Gehry’s first commission in his hometown. Four years later, when Gehry’s work was unveiled, it received critical acclaim. The AGO’s massive new facade, composed of glass and wooden beams, was praised for its modest beauty. Now it has cemented itself as an iconic part of Toronto’s growing skyline. — Joshua Chong

2007

ROM opens the Michael Lee-Chin Crystal

No structure in Toronto is more controversial than the Royal Ontario Museum’s Michael Lee-Chin Crystal, which opened in 2007 with a eye-watering price tag of $416 million. Critical reaction at the time was divisive, echoing the sentiments of the broader public. The Toronto Star’s former architecture critic, Christopher Hume, lauded the museum’s new wing as “21st-century architecture at its most brilliant.” Meanwhile, the Globe and Mail’s former architecture critic, Lisa Rochon, was already waiting for the day the “tin pinata” would be torn down and replaced. Nearly two decades later, the Crystal still hangs over Bloor Street, though an ongoing renovation will see it receive a significant facelift. — Joshua Chong

2006

Toronto gets a dedicated opera and ballet house

The campaign to build a dedicated venue in Toronto for opera and ballet took so long, hampered by a litany of political and financial challenges, that the Canadian Opera Company’s former general director, Richard Bradshaw, called it his “30-year war.” When the Four Seasons Centre for the Performing Arts did finally open in 2006, it marked a culmination of that long struggle. The new development on University Avenue was meant to succeed the unwieldy Meridian Hall, formerly known as the O’Keefe Centre and Hummingbird Centre. Though the building initially was greeted with mixed reviews (its rather bland exterior received much of the criticism), it’s now widely regarded as one of the best venues acoustically on the continent. — Joshua Chong 

2005 

A cutting-edge new catwalk debuts

The Six joined the international roster of catwalk cities in 1999 with the launch of Toronto Fashion Week. But designer Vanja Vasic still felt like something was missing in the city’s sartorial landscape. Where was the inclusivity? The diversity? The accessibility? She wanted to create a more boundary-pushing event that would welcome all designers, no matter how wild their designs, so she started Fashion Art Toronto (FAT) to promote our city’s freakier fashion visionaries. Two decades later, Fashion Week Toronto is no more, but the underdog FAT continues unabated, celebrating 20 years of cutting-edge catwalks. — Briony Smith

2004

The Drake Hotel is Toronto’s new chic clubhouse

The Drake Hotel helped cement West Queen West as the hot neighbourhood of the era, acting as an honorary clubhouse for everything mid-aughts cool. Lines snaking around the block — even in the dead of winter — were a common sight as the guys, girlies and gays jostled to get into the hottest parties in town. Indie sleaze and bumping dance parties were in full swing at the Drake Underground music space, while folks crowded onto the rooftop Sky Yard for fancy cocktails and packed the patio for brunch (despite the hotel eateries’ notoriously terrible service). The Drake would spawn many cottage industries, from the Drake General Store to various outposts both in Toronto (we still mourn the Drake Commissary up on Sterling) and further afield (out in happening Prince Edward County), but the old days at the OG hotel will always hold a special place in many millennial hipsters’ hearts. — Briony Smith

2003

The Rolling Stones help Toronto recover from SARS

An outdoor concert featuring the Stones, Rush, AC/DC and Justin Timberlake. Appearances by Dan Aykroyd and Catherine O’Hara. Premier Ralph Klein serving up Alberta beef sandwiches. Nearly 500,000 fans braving the sweltering summer heat. It’s a miracle to think that “Molson Canadian Rocks for Toronto” — the official name of the massive concert benefit at Downsview Park better known by the moniker “SARS-Stock” — was pulled together in less than two months. Organized in the wake of a SARS outbreak that killed 44 Ontarians and devastated Toronto’s tourism sector, the benefit attracted legions of fans from across the country and from the U.S. to become the largest outdoor ticketed event in Canadian history. More than that, SARS-Stock was a display of immense resiliency, showing the world that Toronto will always get back on its feet. — Richie Assaly

2002

Roy Thomson Hall tries to fix an acoustical mess

The opening of Roy Thomson Hall in 1982 offers important lessons about how not to advertise a new venue. In the run-up to the unveiling, press releases promised the new home of the Toronto Symphony Orchestra would not just be a fine hall, but the finest hall in the world. Talk about overhyping something to the extreme. In reality, the hall probably offered one of the worst acoustical experiences, described by critics and musicians as exceedingly cold and with dead spots throughout the auditorium. In 2002, after years of complaints, the hall finally closed for several months to facilitate a $20-million renovation, which saw the addition of a wooden canopy above the stage to help improve acoustics. It by no means turned Roy Thomson Hall into “the finest hall in the world,” but the changes were noticeable and largely for the better. — Joshua Chong

2001

A “Degrassi” reboot introduces us to a fresh-faced Drake

“Degrassi: The Next Generation,” which first hit the airwaves in the fall of 2001, was the fourth series in the Canadian-made “Degrassi” franchise and would go on to be the longest, running for 14 seasons through to 2015. During that time, it became one of the most watched youth dramas in North America. And not only did it put Toronto on the map (the series was filmed across the city, including on its namesake De Grassi Street, near the Riverdale neighbourhood), it also introduced a cadre of fresh-faced actors who would go on to be household names. Drake, anyone? — Joshua Chong

2000

“Mamma Mia!” makes a splash in Toronto

“Mamma Mia,” the ABBA-inspired jukebox romp, marked its North American premiere at Mirvish’s Royal Alexandra Theatre in 2000. By the time it closed five years later, the production cemented itself as one of the most successful theatre shows in the city’s history. It brought in more than $200 million in ticket sales and was seen by more than 2.8 million people, equivalent to about half the population of Toronto at the time. The show also ushered in a new era of jukebox musicals in the city and propelled Canadian actor Louise Pitre to a Tony nomination in 2002 when she reprised her role on Broadway. — Joshua Chong