Taylor Swift Eras Tour Toronto Odds: Which Celebrity Guest(s) Will Appear on Stage?

If there’s one thing that Taylor Swift loves to do on tour, it’s to surprise her audience with a special guest.

It’s a tradition that started with the Fearless Tour and reached its peak during the 1989 World Tour (which featured at least one surprise guest each night). Special guests on the Eras Tour have been more sporadic, but they’ve ranged from featured artists on Taylor songs, to producers, to friends, to opening acts.

Surprise guests sometimes appear at shows in their hometowns, states, or countries, and are common at big nights like the final show or a tour leg or one where a music video is debuted. With only fifteen Eras shows left, every show seems like a big night and whatever surprises Taylor has planned are bound to be bigger and better than ever. That first three shows of the leg already featured guests spots from Florence + the Machine – and we’re just getting started!

Taylor plays a record-breaking six nights at Toronto’s Rogers Centre next month. It’s one of the tour’s longest stretches of shows in one city and makes up the majority of the remaining concerts. A surprise guest at at least one night in Toronto seems almost guaranteed. The question is, who?

Let’s savor the latest addition to our Taylor Swift odds library and break down some of the potential candidates (odds courtesy FanDuel Canada as of Oct. 28 at 8:30 a.m. ET):

Celebrity Guest Appearance on Stage at the Eras Tour Toronto

Celebrity Guest Appearance Favorites

Gracie Abrams (-1500)

No one is busier than Taylor, but Gracie comes close. She opened fourteen shows during the first North American leg of the Eras Tour, took a break to drop an album (which included the Taylor collab, “us”), performed the US leg of her tour, and is now back to open all eighteen shows of the final Eras leg. She’s already appeared twice during the acoustic/surprise song set, most recently performing “us” with Taylor in London on June 23.

It’s a pretty safe bet that Gracie will join Taylor on stage again before the tour is out. If even bigger things are in the works for the final three shows in Vancouver, Toronto might be the perfect time for that.

Shawn Mendes (-160)

Shawn opened for Taylor on the 1989 World Tour, was a special guest on the Reputation Stadium Tour, and collabed with her on a remix of the titular track from her seventh album, Lover. Needless to say, Shawn is very much a part of the Taylor Swift Cinematic Universe (TSCU). Better yet, he’s from Ontario! What better way to make an Eras Tour appearance than at what’s essentially a hometown show?

That said, his guest spot on the Reputation Stadium Tour was in Pasadena, so hometown loyalty might not be a deciding factor.

Aaron Dessner (-160)

Aaron has appeared on the Eras Tour six times, holding the record for any surprise guest. Until now, he has only joined Taylor on stage for US shows, in Tampa (twice), Nashville, Pittsburgh, Cincinnati, and Santa Clara. His Santa Clara show (which I was supposed to attend and missed thanks to illness) was all the way back in July 2023.

As one of Taylor’s two main musical collaborators, it’s hard to believe he won’t make another appearance on the Eras stage. And, if Dessner’s absence during the international shows was due to distance or travel, Toronto would be a perfect option – of the final cities, it’s the closest to his home and studio in upstate New York.

Post Malone (+250)

As a collaborator on “Fortnight,” the lead single from The Tortured Poets Department, Post is an obvious choice for a special guest spot (in fact, the Eras crowd goes crazy when one of Taylor’s dancers appears at the beginning of “Fortnight” each night, thinking it’s him). 

The album’s other featured artist, Florence Welch (of Florence + the Machine, which carry +380 odds), has appeared at four Eras shows thus far. Since “Fortnight” is already on the setlist, Post (like Welch) would appear during the TTPD set rather than the acoustic set. But a surprise guest is a surprise guest no matter when!

Celebrity Guest Appearance Underdogs

Ice Spice (+600)

Ice Spice appeared at all three Eras shows at Metlife Stadium back in May 2023. She joined Taylor for the show’s final number, “Karma,” to perform her verse from the song’s remix. The Ice Spice appearances came directly on the heels of the remix’s release, and as a New York City native, Metlife is her hometown stadium. 

She and Taylor have developed a friendship so it isn’t out of the question that she’ll appear again, but as repeat guests go, she seems unlikely to me.

Brendon Urie (+600)

Brendon collaborated with Taylor on 2019’s “ME!”. Despite being Lover’s lead single, the song was met with mixed reactions even from Swifties. It is notable that “ME!” was not included on the Eras setlist, unlike Lover’s other two pre-album releases, “You Need to Calm Down” and “Lover.”

Additionally, Brendon discontinued Panic! At the Disco and announced his retirement in early 2023 to focus on his family. The Eras Tour is a cultural phenomenon, but is it enough to drag him out of retirement to sing a song that underperformed? I’m skeptical. 

Drake (+750)

While Drake is a Toronto native, his history with Taylor is complicated. At one point, they seemed friendly, posting pictures together. Before Lover’s release, Swifties even speculated that Taylor left Easter eggs indicating a Drake collaboration, but nothing ever materialized.

Drake seemed to throw shade at Taylor in an Instagram story in 2022 after her single “Anti-Hero” stayed at number one and kept him from occupying all ten spots atop the billboard charts – that’s a feat that only Taylor has accomplished, and she’s done it twice. However, he later praised her on a track, stating she was the only one who could make him drop an album a little later. 

Perhaps most importantly, Drake is famously locked in a nasty feud with Taylor collaborator and friend Kendrick Lamar. Lamar has made some serious accusations on not one but two albums devoted to his beef with the other rapper. In my opinion, this guest appearance is unlikely. 

Alanis Morisette (+750)

Another Canadian native, Alanis was a special guest on the 1989 World Tour. (Her appearance, like Shawn Mendes’, was in California rather than Canada.) 

Plus, Alanis is an icon to millennial women – every song on Jagged Little Pill is forever embedded in my DNA – and Taylor is as millennial as they come.

Jack Antonoff (+750)

Fair warning: I can’t be normal about this one.

Jack is Taylor’s number one collaborator and, as she once said, he is musical family at this point. These two have been making music together since pre-1989 and it is hard to imagine Taylor will ever release an album without at least one Jack-produced and/or cowritten track again. (This is a blessing to me specifically because I can talk about the merits of a Swift/Antonoff bridge for literal hours. And I have. Apologies to anyone who has ever said “bridge” in any context while in my presence over the last decade.)

Jack has appeared on the Eras Tour twice: at Metlife Stadium in his home state of New Jersey, and on closing night in London in August. I was present for the latter and have never screamed harder in my life than I did when they paused their mash-up of “Death By A Thousand Cuts” and “Getaway Car” to act out the iconic scene in Miss Americana where they write the “Getaway Car” bridge in a matter of seconds. I’m experiencing a dopamine hit just thinking about it and I was far from the only Swiftie in the audience reacting accordingly. We all know Taylor loves to give the fans what they want, so, like Aaron Dessner, I imagine we’ll see Jack at least one more time before the tour ends on Dec. 8th. 

Personally, as a certified Antonoff fangirl, I am hoping it’ll be on Dec. 8th when I’ll once again be in the audience, but there’s only one closing night and he’d also be an excellent and likely addition to the Toronto festivities. 

Maren Morris (+750)

After having her as a special guest on the Reputation Stadium Tour, Taylor invited Maren to feature on “You All Over Me,” a vault track on Fearless (Taylor’s Version). Maren joined Taylor’s on the Eras Tour to perform the song in Chicago back in June 2023.

While that was certainly long enough ago that she could feasibly make a second appearance, it’s worth noting that Maren’s own tour doesn’t wrap up for the season until Nov. 20th, halfway through Taylor’s stint in Toronto. She might need some rest.

Avril Lavigne (+750)

Like Alanis, Avril is Canadian, a 1989 World Tour special guest, and an icon to millennial women everywhere. Her guest spot was in, you guessed it, California.

Kendrick Lamar (+1000)

Kendrick has never performed live with Taylor despite featuring on both the original and Taylor’s Version of 1989’s “Bad Blood” remix. Every night, the Eras crowd chants Kendrick’s line, “You forgive, you forget, but you never let it go”; maybe it's time for him to join them?

Chris Stapleton (+1100)

Chris collaborated on the Red (Taylor’s Version) vault track, “I Bet You Think About Me.” He lives in Nashville, but the Toronto dates correspond with a break in his touring schedule.

Selena Gomez (+1100)

Once upon a time, in 2008, Taylor and Selena dated Jonas Brothers at the same time and became besties. The relationships didn’t last, but the friendship has been enduring. Selena has joined Taylor as a special guest at the Speak Now World Tour, the 1989 World Tour, and the Reputation Stadium Tour.

By my count, she’s attended Eras three times (Arlington, Los Angeles, and Gelsenkirchen), but strictly as an audience member. The ladies clearly love performing together, but in recent years, Selena has been much more focused on acting and advocacy. She’s only performed live a handful of times since 2019 and the most recent instance was over a year ago. This significantly lowers the likelihood of an Eras Tour appearance.

But if anyone can coax Selena out of this semi-retirement from the stage, it’s Taylor.

Lana Del Rey (+1300)

Lana is featured on the Midnights track “Snow On The Beach.” When fans complained there wasn’t enough Lana on the album version, they released a second version, “Snow on the Beach (feat. more Lana Del Rey).” The pair have never performed the song together live, and Lana has never been a special guest on any of Taylor’s tours. Perhaps now is the time to change that.

Keith Urban (+1300)

Keith provided background vocals on two vault tracks from Fearless (Taylor’s Version), “That’s When” and “Don’t You”. It was a beautiful full circle moment as back in 2009 when she was promoting the original Fearless, Taylor was opening for Keith. They’ve never performed either song together live.

The Australian country singer was a special guest on the 1989 World Tour. Guess where? Toronto!

Bon Iver/Justin Vernon (+1300)

Bon Iver frontman, Justin Vernon, has joined Taylor on two tracks: Folklore’s “Exile” and Evermore’s title track. The songs were recorded from afar during the height of the pandemic, and the pair performed “Exile” live from different studios for the 2020 film “Folklore: the Long Pond Studio Sessions”. They have never performed together live. 

Both tracks are fan favorites so a Bon Iver guest appearance would cause just the sort of uproar one might expect from the final leg of the Eras Tour.

Fallout Boy (+1600)

Taylor performed with Fall Out Boy during the 2013 Victoria’s Secret Fashion Show, lead vocalist Patrick Stump was a special guest on the 1989 World Tour, and the band was featured on the Speak Now (Taylor’s Version) vault track “Electric Touch”. 

Seeing Stump at an Eras Tour show is a possibility, but I would have expected it back in 2023 when Speak Now (Taylor’s Version) was both announced and released.

Marcus Mumford (+1600)

Mumford provided background vocals on the Evermore track “Cowboy Like Me”, which was recorded at his studio in London. He sometimes sings “Cowboy Like Me” at his shows and joined Taylor to perform the song during the Eras Tour acoustic set in Las Vegas. 

While his guest appearance was at only the fourth Eras show ever, almost two years ago in March 2023, he lives in London and I’d be surprised to see him again on this tour.

Phoebe Bridgers (+1900)

Phoebe collaborated on the Red (Taylor’s Version) vault track “Nothing New,” and opened for nine Eras Tour shows in 2023. For those nine shows, “Nothing New” was added to the setlist with Taylor inviting Phoebe to the stage each night during the Red set to perform the song together. Perhaps Bridgers will return for one more performance before the end.

Celebrity Guest Appearance Longshots

Travis Kelce (+2400)

Kelce appeared onstage during the June 23rd show in London this summer, joining two dancers playing the comedic role of vaudeville-style businessmen forcing her to perform against her will. Taylor might like to have him appear again before the end of the tour, but that could be complicated by the NFL season, which is in full swing. 

Taylor performs in Toronto Nov. 14-16 and 21-23, while Kelce and the Chiefs have games on the 10th, 17th, and 24th.

Ed Sheeran (+2400)

Ed and Taylor are old friends at this point. He collaborated on Red’s  “Everything Has Changed”, opened for the Red Tour, and has collaborated with Taylor on multiple tracks since. Ed was also a special guest on the 1989 World Tour and appeared at the London Eras show on Aug. 15th. 

He’s a pretty busy guy, so I’d be surprised to see him trek to Canada for a second appearance.

Justin Bieber (+4800)

Yeah, he’s Canadian. And, yeah, he was a special guest on the Speak Now World Tour. But that was before the Selena break-up, the Kanye Facetime bullying, and the whole thing where Scooter Braun bought Taylor’s masters and served as the catalyst for her to re-record her first six albums.

This one is a long shot. 

My Pick

It’s unlikely that the Eras Tour will end without Gracie Abrams, Aaron Dessner, and Jack Antonoff gracing the stage again. Since more than a third of the remaining shows are in Toronto, odds are good that at least one of them will make an appearance in the 416.

For a longer shot, bank on an appearance from one of Canada’s finest and go for Shawn Mendes, Alanis Morisette, or Avril Lavigne.

Pro Tip: If you’re betting on Jack Antonoff then, song-wise, “Death By A Thousand Cuts” and “Getaway Car” are a good place to put your money. Jack has performed “Getaway Car” at both of his Eras appearances; requested “Death By A Thousand Cuts” at one show and performed it at another.

Other Options

• Florence Welch joined Taylor to perform “Florida!!!” at the final London show and all three Miami shows. That’s likely because London is her home and Miami is, you know, in Florida.

• Canadian icon Bryan Adams and Taylor performed “Summer of ‘69” on the Reputation Stadium Tour and she sure looked like she was having a lot of fun.