Taylor Swift loves Canada: the pop star's Canadian connections

It's been a long time since Taylor Swift first played Toronto in 2006, as a last-minute opening act for Rascal Flatts at the Air Canada Centre (now Scotiabank Arena). 

In the almost two decades since then she's become an absolute pop phenomenon, and over the last nearly two years Swift's Eras tour has taken the world by storm. By the end of 2024, the tour is expected to gross $2.165 billion. After kicking off in March 2023, it finally touches down on Canadian soil with six sold-out shows in Toronto between Nov. 14 to 16 and Nov. 21 to 23 at the Rogers Centre. The tour will conclude in Vancouver, over three sold-out nights between Dec. 6 to 8 at BC Place.

Swift has stopped in Canada during all of her headlining tours since 2009, visiting Edmonton (seven times) and Toronto (10 times) most frequently. Other cities including Calgary, Winnipeg, Ottawa, Montreal, Vancouver and even Craven, Sask., and Cavendish, P.E.I., have been graced by Swift's presence over the years. From the very beginning, back in her Speak Now days, Swift's been loyal to her Canadian fans. 

There is also a plentiful list of Canadians with whom she's worked over the years on her albums, music videos, official remixes and live shows. Discover Swift's most notable Canadian connections below.  

The mastermind behind the Eras live show

Ethan Tobman is the creative director of the Eras tour, one of the most ambitious live shows in history. The Montrealer has been working as a production designer and director since the early 2000s and had worked on a number of Swift's music videos ("Cardigan," "Anti-Hero," Karma," "Bejeweled" and more) before getting the chance to lead the creative vision for her concert visuals.

He crafted an impressive, malleable set design that shifts with Swift's distinct eras, as she performs songs from across her 11 albums. From billowing, pastel-coloured sheets that rise high above the pop star, to graphics that switch based on the mood of each song, to pyrotechnics that would make Nickelback gawk, to an illusion that makes it seem as if Swift is swimming under the stage — it's a non-stop spectacle. 

In an interview with the Toronto Star, Tobman was tight-lipped about his process in dreaming up the set design, but did share how grateful he was to be chosen: "I didn't go after the job, I hadn't really even dreamt of doing live performance. And I was so extraordinarily grateful when my relationship with Taylor, having done music videos, had developed to become something more elaborate than just short form, and where she invited me to be part of this process."

On top of his work with Swift, Tobman has also worked with Beyoncé and Eminem, and won the 2024 Juno Award for video of the year for his direction of Allison Russell's "Demons." 

Inspired covers and surprise guests

Other than the "Lover" remix featuring Shawn Mendes, Swift doesn't have many official collaborations with Canadian artists, but she's still a big fan and shows her love by covering their music during her live sets. At her July 2011 show in Toronto, Swift played a pared-back rendition of Justin Bieber's 2008 smash hit "Baby." Before starting the song, she told the crowd: "I just have to represent for my boy, who's from here," and they went wild, screaming as soon as she played the first chord on her acoustic guitar. 

In August 2013 she brought twin sister duo Tegan and Sara well out of their comfort zone when she had them as surprise guests at her tour stop at the Staples Center in Los Angeles. Tegan told Rolling Stone that the sisters saw similarities between their music, and the appearance felt like a good fit: "We always say we're emo — that's our genre. And I think Taylor's emo. She talks about her feelings. She doesn't pretend or hide who she is or how she feels about things. We have that in common."

As Swift sang the second verse, she decided to strut down the catwalk and the sisters did their best to keep up with the singer's larger-than-life persona: "I was like, I would never do that! I've never even sung with a wireless mic before. I'm going to try not to trip and fall in front of all these people ... I'll skip along next to you. It was her stage. We were just honoured to be asked," Tegan said in the same interview. 

Although she had performed "Complicated" by Avril Lavigne a number of times while touring over the years, Swift didn't get to perform the song with the Canadian pop-punk princess until her 1989 tour date in San Diego in 2015. During the same tour at a Los Angeles show, she brought Alanis Morisette onstage to perform "You Oughta Know," introducing the '90s icon as someone who "defined the music of her decade." Swift went on to say that Morisette "inspired a generation of confessional female singer-songwriters who all of a sudden felt like you could actually say these raw feelings that you had, you could actually sing about your real life." 

Shawn Mendes opened for Swift throughout her 2018 Reputation tour, including stops in Toronto and Vancouver. His second studio album, Illuminate, had been released the previous year and the breakaway hit single, "There's Nothing Holding Me Back," was inescapable. One night in Pasadena, Calif., Swift decided to bring Mendes out during her set and they performed the song together, which sent the crowd into an absolute frenzy. On the same tour, Swift brought out Bryan Adams at the Rogers Centre in Toronto to perform "Summer of '69," calling it one of her "favourite songs ever written."

The time Swift sampled a Toronto youth group

"It's Nice to Have a Friend" uses a composition called "Summer in the South" created by the Regent Park School of Music in Toronto. You can hear their steel pan, violin, saxophone and angelic voices from the very first seconds of the song. "It's Nice to Have a Friend" was produced by Toronto's Frank Dukes (as well as Swift and Louis Bell), who works frequently with the music school. One of the initiatives Dukes created through the Kingsway Music Library is Parkscapes, which funds music education programs when artists purchase samples from its library of compositions, beats, vocals and more. Money from sample clearances and royalties have been used to continue funding the program. 

"Spending time with the kids who were a part of the program, it was really inspiring for me to see how having them become a part of something where they really felt engaged and inspired helped open up their eyes to see how big the world is," Dukes said in an interview with CBC's q. "That if they really want something they just have to do it and they can get it and it's all within reach." 

Unexpected remixes 

Since she leans more into the pop/country/folk side of music, it's always a surprise when Swift releases official electronic remixes of her singles. It doesn't happen all that often, but for two recent remixes she tapped Canadians Jayda G and Blond:ish. Jayda G hails from Vancouver, and her 2022 remix of "Anti-Hero" from Swift's album Midnights turns the self-critical song into a disco-house bop. Earlier this year, Montreal DJ and producer Blond:ish remixed "Fortnight," the lead single off Swift's latest album, The Tortured Poets Department. As CBC Music said when the remix was first released, Blond:ish's version raises the sonic stakes of the song, and "with a climbing beat, Swift's tale suddenly feels like a roller-coaster ride that better reflects the song's emotional ups and downs."