The Hollywood Insider – Sabrina Carpenter Lollapalooza
From surprise guest appearances to genre-blending headliners, this year’s fest proved why Lolla still sets the tone for summer.
Every summer, Grant Park transforms into a sprawling playground for music lovers, and Lollapalooza remains its crown jewel. Born in 1991 as a touring festival founded by Perry Farrell of Jane’s Addiction, Lolla eventually settled in Chicago in 2005, where it has grown into one of the largest and most diverse music gatherings in the world. Known for blending genres, introducing future superstars, and creating those once-in-a-lifetime collaborations, it’s a celebration of sound, sweat, and shared moments.
This year’s lineup was a testament to that ethos. Headliners Olivia Rodrigo, Korn, TWICE, Rüfüs Du Sol, Tyler, The Creator, Luke Combs, and Sabrina Carpenter gave fans everything from raw punk-pop energy to nu-metal nostalgia, K-pop precision, and shimmering dance anthems. Across four days, Chicago’s skyline framed stages filled with generational icons, genre-bending newcomers, and more than a few surprises.
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Day One: Kicking It Off
Thursday opened with Chicago’s own Ratboys and the collective Chicago Made, both proudly representing the city’s thriving indie scene. Role Model’s set was one of the day’s unexpected crowd-crushers, proof that his following has skyrocketed well beyond what his stage size could handle.
Gracie Abrams delivered a polished and emotionally resonant performance, winning over skeptics with her improved live vocals and unexpected star power. The real jaw-dropper came when she brought out Robyn to duet “Dancing On My Own,” a full-circle nod to her Lolla debut when she covered the song.
Tyler, The Creator’s headline slot was pure magnetism, just him, a massive stage, and the charisma to make it feel intimate. Luke Combs, meanwhile, made history as the festival’s first country headliner, belting out hit after hit to a sea of country fans eager to see their genre represented.
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Day Two: Olivia, Korn, and a Midday T-Pain Dance Party
Friday’s early hours belonged to Gigi Perez and Del Water Gap, who drew unexpectedly huge audiences despite the heat. Del Water Gap balanced cool detachment with moments of vulnerability, even restarting a song mid-set after a technical glitch, earning extra affection from fans.
T-Pain turned the Bud Light stage into the biggest party of the festival. His one-hour set crammed in decades of hits, his own and others’, and proved that behind the Auto-Tune legend is a powerhouse vocalist.
Then came Olivia Rodrigo’s long-awaited Lolla Chicago debut. Backed by an all-female band, she tore through tracks from SOUR and GUTS, balancing heartfelt ballads with mosh-ready anthems. The night’s most talked-about moment came when she brought out Weezer to perform “Buddy Holly” and “Say It Ain’t So,” a nod to the first concert she ever attended. She finished it all with fireworks and a four-song encore, cementing her place as one of pop’s defining voices.
Over on the opposite side of the park, Korn returned to Lollapalooza for the first time in 28 years, delivering a crushing set that nodded to their early work while embracing nu-metal’s modern revival. For fans, it was equal parts nostalgia trip and masterclass in heavy rock showmanship.
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Day Three: Pop Icons, Rap Stars, and a Touch of Disco
Saturday morning started soft with sibling duo Wasia Project, followed by a glowing set from Marina, back at Lolla for the first time in a decade. She mixed recent tracks with the anthems that made her a Tumblr-era icon, proving her pop star charisma is as potent as ever.
Clairo brought a dreamy blend of old and new tracks, while Doechii turned her debut into a theatrical masterclass in performance stamina. Staging her set like a “hip-hop classroom,” she blended flawless choreography with airtight rapping and teased an upcoming tour.
TWICE drew one of the day’s largest crowds, dazzling with high-energy choreography, hits like “Fancy” and “Feel Special,” and a drone show tie-in with their film ‘KPop Demon Hunters’. Across the park, Rüfüs Du Sol closed the night with a hypnotic set that had thousands swaying under the Chicago night sky.
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Day Four: Closing with Powerhouse Performances
Sunday’s energy was still high despite three days of marathon music. Girl group KATSEYE turned their afternoon slot into a headline-worthy spectacle, delivering slick choreography, powerhouse vocals, and live debuts of fan favorites like “Gabriela” and “M.I.A.”
Dominic Fike’s laid-back approach contrasted with The Marías’ lush indie-pop grooves, while A$AP Rocky brought raw energy, though the strict 10 p.m. curfew cut his set short.
Then came Sabrina Carpenter to close out the south end of the festival. In just two years, she’d gone from a midday side-stage performer to a main headliner, and she embraced the moment with full theatrical flair. Her Short n’ Sweet album was performed in its entirety, accented by vintage-inspired visuals and playful, risqué stage bits that only Carpenter could pull off. The biggest surprise of the night was a mid-set appearance by Earth, Wind & Fire, turning the field into a disco fever dream with “Let’s Groove” and “September.” She wrapped with “Espresso” under a shower of fireworks, an unapologetically joyful end to the weekend.
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The Best of the Rest
Beyond the headliners, Lolla 2025 offered dozens of moments worth remembering:
- Bleachers leaning into their Springsteen-meets-Bowie influences, turning “Rollercoaster” into a shoulder-sitting singalong.
- Amaarae blending Afrobeats, pop, and hip-hop into a sultry, high-energy set that doubled as a sneak peek of her upcoming album Black Star.
- Orla Gartland transforming her set into a dazzling indie-pop party.
- Otoboke Beaver proving why they’re one of punk’s most thrilling live bands.
- Still Woozy radiating pure joy, with crowd-surfing and infectious energy that made it impossible not to sing along.
- Wallows reminding fans why their mix of breezy alt-rock and heartfelt lyricism has kept them festival favorites.
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A Festival That’s Still Evolving
One of the standout takeaways from this year wasn’t just the music; it was the lineup’s gender balance at the top. Five of the ten biggest slots went to women, each delivering a set that proved they belonged there. From Olivia Rodrigo’s generational pop performance to Sabrina Carpenter’s theatrical finale, Lollapalooza 2025 made space for women to dominate without being pigeonholed into a single sound or style.
And like every great festival, it wasn’t just about the acts themselves; it was about the shared experiences: strangers bonding over a lyric, the skyline glowing behind a stage, or a set you wandered into and left a new fan. After four days, 170+ acts, and a few miles of walking, it’s clear Lollapalooza’s magic is still alive and well.
The stages are empty now, Grant Park is quiet again, but somewhere, someone’s already planning their 2026 setlist. And after this year’s highs, the bar has never been higher.
By Elizabeth Gelber
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Elizabeth Gelber is an aspiring film and television producer and writer with a love for all things media, from music to fashion to entertainment. With a background in Television, Radio, and Film, as well as Fashion Communications, she is passionate about telling female-led stories that empower and resonate. Her work blends wit with empathy, aiming to humanize entertainment through an authentic lens. She believes the most powerful narratives are often rooted in everyday life, and she is drawn to creating media that reflects the world as it truly is, diverse, imperfect, and meaningful.
Elizabeth Gelber is an aspiring film and television producer and writer with a love for all things media, from music to fashion to entertainment. With a background in Television, Radio, and Film, as well as Fashion Communications, she is passionate about telling female-led stories that empower and resonate. Her work blends wit with empathy, aiming to humanize entertainment through an authentic lens. She believes the most powerful narratives are often rooted in everyday life, and she is drawn to creating media that reflects the world as it truly is, diverse, imperfect, and meaningful.
