Sabrina Carpenter’s highly anticipated return to Lollapalooza was just the sendoff her iconic Short n’ Sweet era deserved. Not only did it mark her comeback to the Chicago-based festival since 2023, but her last performance this summer before her seventh album, Man’s Best Friend, drops later this month.
It’s a complete 180 compared to the last time I watched her sing on the eve of Short n’ Sweet’s release, when she pretty much secured her Grammy with a performance of “Please Please Please” on The Tonight Show Starring Jimmy Fallon. Now, she’s got two golden gramophones under her belt with another record on the horizon and a headlining gig at one of the biggest music festivals in the biz.
While it may not have been my first time seeing her live, it was my first time in Chitown for Lolla, thanks to an invite from T-Mobile to check out the hottest club in town: Club Magenta. As a pop culture editor who’s constantly frolicking across festival grounds, I was personally saved by the unmatched VIP access I was given in the exclusive area all weekend. The elevated, shaded lounge kept festival-goers cool, connected, and close to the action with merch giveaways, free drinks from 6 to 7 p.m. every day, and, of course, a perfect view of the T-Mobile stage, where Sabrina headlined.
Maybe it was the delicious stream of cool air, my constant clutch of Club Magenta’s complimentary portable chargers, or the ice-cold drink in my hand, but I knew I was in for an absolute treat during Sabrina’s set. Thanks to these perks, I realized that maybe I’m not meant to live an uncomfortable life during festival season. So, consider me spoiled—it’s what S.C. would want.
Sabrina’s vocals are stronger than ever, her hooks are sticky-sweet, and her pen? It’s always been criminally sharp. The pint-sized pop star has always been larger than life through her dry humor and infectious stage presence, which kicked into gear when she opened the show with “Busy Woman.” Her ’60s-inspired stage set mirrored that of her ongoing Short n’ Sweet Tour and the pastel retro aesthetic she’s embraced since 2022.
She kept the vibes going with tracks like “Good Graces,” “Coincidence,” and “Slim Pickins.” Then, it was time for her to bring “Manchild” to the U.S. Lollapalooza marked her first performance of Man’s Best Friend’s chart-topping lead single in the states, which resulted in a sea of lingerie-clad and platform-stomping festival-goers flawlessly executing her cheeky TikTok choreo in the crowd.
I’ll admit, hearing thousands of people scream “stupid,” “slow,” and “useless” was probably one of the best things I’ve experienced during a live show—after all, we were working late, ’cause we’re singers. Obviously.
A similar feeling took over once she burst into “because i liked a boy,” except there was a sense of serenity that came from the woman singing it before us. When it was released in 2022, Sabrina was in the thick of a headline-making love triangle that we don’t even know to be true.
Three years later, she’s become so much bigger than that—so much so, that she brought out Chicago natives Earth, Wind & Fire for a performance of “Let’s Groove” and “September” immediately after. Seeing musical icons from a certain era mesh so seamlessly with new-age talent not only gave me goosebumps, but also reminded me that the beauty of such moments is universal. It truly felt like an honor to witness, so I can’t even imagine what it’d be like on stage.
And, while half the internet was probably holding out hope that fellow Lollapalooza headliner, Olivia Rodrigo, would be Sabrina’s “Juno” girl, it ended up being another headlining act, TWICE. The moment was sweet, and while there was a minimal “Juno” position of her “flicking” a mini replica of the bean into the crowd, the joy of getting low, screaming “I’m so fucking horny,” and jumping right back up to dance is irreplaceable.
Of course, the show closed with the song that catapulted Sabrina into mainstream superstardom, “Espresso.” No matter how overexposed it is at this point, moments like these only get better when you realize the whole world is finally listening. Whether you’ve subscribed to Sabrina’s stardom since “Can’t Blame a Girl for Trying” or discovered her on Taylor Swift’s Eras Tour, one thing’s for certain: She always believed she was on top.
I had long seen her potential after watching her perform—at the Radio Disney Music Awards, of all places—in the early aughts of her career. Then, in between her Disney departure and big break (thanks to a cup of “me espresso”), I found songs like “Paris” and “In My Bed” in my rotation. It wasn’t until she released her first album under Island Records, emails i can’t send, that she broke out of being cast as a footnote in someone else’s heartbreak saga—she had her own story to tell, in her voice.
And, corniness aside, there’s comfort in knowing such synergy can happen after years of working hard and self-belief. No matter what our dreams are, we’re constantly sold the story of an overnight sensation. Sabrina is a prime example that a meteoric rise isn’t for everyone—she’s rightfully earned every accolade and headlining gig, despite being told that her slow and steady steps toward greatness made her the tortoise instead of the hare.
Well, now she’s at the top of her game and on top of the world.
