Madonna Air Canada Centre, Toronto ON, October 5

Madonna Air Canada Centre, Toronto ON, October 5
Photo: Rick Clifford
For a seven or eight-song span last night (October 5), pop icon Madonna had the crowd firmly in the palm of her hand.
It began, about halfway through the singer's Rebel Heart Tour stop at Toronto's Air Canada Centre, with a slightly slowed but emphatic rendition of "Isla Bonita" that featured cajóns, and moved through a Peruvian-styled medley of "Dress You Up," "Into the Groove" and "Lucky Star." After maybe the loudest cheers of the night, she played "Who's That Girl" and a surprisingly affecting "Rebel Heart" on an acoustic guitar before leaving the stage briefly so that her backup dancers could display some feats of acrobatic glory during interlude "Illuminati."
A slow, jazzy intro led into "Music," which mixed energy, visuals and one of Madonna's best vocal takes into the night's highlight performance before carrying that momentum into "Candy Shop" (a song whose mediocrity was transcended by its performance) and a hip-hop-influenced, swaggering version of "Material Girl."
If only the show had found that stride ten songs sooner.
Three decades into her career, Madonna knows how to build a successful set list, but on this tour, she seemingly followed her Rebel Heart's every whim, indulging deeply in her unremarkable new album and ignoring many of her most beloved hits — often at the cost of the crowd's attention. There were a handful of occurrences where she asked the quiet crowd if they were "shy"; mostly, they seemed to be waiting for songs they recognized. With such a vast array of hits at her disposal, it felt odd — stubborn, even — that her set list included 12 of her new album's 19 tracks, making for over half the show's uneven 21-song runtime.
Six of the set's opening seven songs were Rebel Heart cuts, each came accompanied by melodramatic, choreographed performances. It was genuinely exciting when Madonna was lowered to the stage in a cage for opener "Iconic," but by the time we'd suffered through the ill-advised, appropriative faux-Asian-themed performance of "Bitch I'm Madonna," complete with hand fans and samurai outfits, and a greaser-themed "Body Shop" set in a garage, it all felt a little over-compensational.
Ever the Artist, Madonna was boldly asserting the importance of her latest album, but Rebel Heart doesn't have the hooks that characterized her previous work. This was perhaps most evident in her stark, ukulele-only rendition of "True Blue," during which one couldn't help but wonder whether newer songs like "Holy Water" or "Illuminati" would hold up given the same treatment. In any case, packing the set with new songs, even when they were performed as well as "HeartBreakCity" was, felt like a miscalculation; it was Madonna, not Rebel Heart, that sold out the Air Canada Centre.
So it felt especially disappointing when, for every great performance (Madonna's simple and effective, crowd interaction-heavy "Like a Virgin"), there was a momentum-killing interlude (the faux-risqué "S.E.X.") or misguided attempt at hyping up the crowd ("Living For Love," which was neither the dynamic, statement song it is on record, nor a particular crowd favourite).
Then, there were the downright baffling decisions. Madonna's acoustic take on the worn-out, clichéd "La Vie en Rose" felt like the moment that guy pulls out a guitar to play "Wonderwall" at a party, while closing her main set with "Unapologetic Bitch" demonstrated a vast overestimation of how much that song resonates with her fans. She left the stage on the lowest note possible, too — after awkwardly strolling out Nelly Furtado to give her a banana and make tired sexual jokes about it. This was as awkward as it sounds. It took a minute for the scattered, awkward applause to build up to the encore, a satisfying rendition of "Holiday."

In the age of "retromania," when Like a Prayer vinyl reissues line the walls of Urban Outfitters and "Into the Groove" soundtracks dance parties, Madonna's '80s and '90s catalogue is as relevant as it's been in decades, making this tour the perfect chance to celebrate and recontextualize that old material. As a creative, it makes perfect sense that Madonna would want to focus on her latest work, but last night felt like a wasted opportunity. Madonna's efforts to stay current ended up making the performance feel less in touch with today than if she'd just played her old hits — not to mention less fun.