Demi Lovato Delights in Madison Square Garden Headlining Debut With Triumphant ‘It’s Not That Deep’ Tour: 5 Best Moments

The clothes rack has been a recurring symbol for the It’s Not That Deep era, so it was only right that it made an appearance onstage Friday night. Lovato used the prop as part of a larger banter section in which she walked the crowd through memory lane, with each look on the rack corresponding to a different album era of hers. Though the whole thing turned out to be a gag to introduce Jojo to the stage, it was still a nice tribute to Demi’s winding career.

Right before the encore, however, Demi reached all the way back to her 2013 self-titled era for “Really Don’t Care,” which she correctly introduced as the “OG ‘it’s not that deep’ anthem.” Playing on similar lyrical themes and power pop vibes, “Really” didn’t just trigger long-buried mid-2010s memories; it also brought the show full-circle in a clear, tangible way — a true testament to the sequencing of the night’s setlist.

Nearly a year ago (May 25, 2025), Lovato married Canadian musician Jordan “Jutes” Lutes, with the adorable couple selecting Goo Goo Dolls’ “Iris” for their first dance. For her headlining MSG show, Lovato didn’t miss the chance to recreate that moment with her husband by bringing him out for a surprise duet of “Iris” in the back half of the show. “What do you say we sing together for the first time?” she quipped with a toothy smile before launching into a duet that turned the arena into an intimate late-night dive bar set. And, of course, their frequent smooches were the cherry on top.

Rising pop star and Dream Academy alumna Adéla may only have a handful of singles to her name, but most of them are absolute bangers — and she fully commits to performing each of them as if they were global chart-topping smashes. Donning hot pink heels and a lacy two-piece outfit, Adéla absolutely rocked the stage like a true pop diva, tearing through club-ready cuts like “KGB” and “Sex on the Beat.” In between serving looks and choreography, she also flaunted her vocal chops with “Homewrecked” and delivered a fiery closer with “Superscar,” perfectly setting the stage for the main event.

With two Grammy nominations to her name, Lovato has long been regarded as one of the strongest vocalists among her pop star contemporaries — and Friday night was yet another reminder of why. Every climax was more thrilling in the last, from her soulful “Tell Me You Love Me” post-chorus ad-libs to the hair-raising belts near the end of the “Confident.” But the real treat was her gametime decision to drop the final, rafters-reaching belt of “Stone Cold” a few steps to ensure an elongated, dramatic finale to one of her most beloved ballads. If anything, Demi’s outstanding vocals — even the lighter moments on standouts like “Low Rise Jeans” — made the absence of Holy Fvck particularly egregious.

In June, Jojo will join the Broadway revival of Chess, taking over the role of Florence Vassy from Lea Michele and starring opposite Aaron Tveit and Nicholas Christopher. Naturally, she’s in town rehearsing for the show, and made the time to stop by Lovato’s MSG show for a surprise duet of “Too Little Too Late.” Most artists dream of having a song with even half the lifespan and cultural longevity of “Too Little,” and the way the sold-out arena yelled every lyric was proof of why. Nonetheless, this moment reached its peak when Lovato and Jojo traded ad-libs at the end. In fact, they should have brought out their 2020 “Lonely Hearts” collab for good measure.