The second day of Lollapalooza 2025 delivered a dynamic mix of nostalgia and firsts as the festival continued in Chicago’s Grant Park. Thursday’s highlights included Olivia Rodrigo’s highly anticipated Lolla Chicago debut, Korn’s long-awaited return after nearly three decades, and standout sets from Bleachers, T-Pain, and Djo.

Olivia Rodrigo Makes Her Lollapalooza Debut

Though it marked her first time performing at Lollapalooza’s flagship Chicago edition, Olivia Rodrigo took the stage like a seasoned headliner. Currently on her Guts World Tour, Rodrigo brought her chart-topping anthems and emotional storytelling to a crowd that sang along to every word. From the moment she opened with “Obsessed” and “Ballad of a Homeschooled Girl,” the energy was electric with one of possibly the biggest crowds the festival has had.

Rodrigo’s set ranged from angsty punk-pop to piano ballads, transitioning seamlessly from high-energy tracks like “Bad Idea Right?” and “Love Is Embarrassing” to the quiet intensity of “Driver’s License” and “Traitor,” performed at the piano with understated elegance.

The night’s biggest surprise came when Rodrigo revealed a personal milestone, her first-ever concert was a Weezer show. She then brought the band onstage for a two-song collaboration, joining them for performances of “Buddy Holly” and “Say It Ain’t So.” Rodrigo closed with an encore that included “Get Him Back!” accompanied by a burst of fireworks, marking a triumphant close to her first Lolla Chicago performance.

Korn Returns After 28 Years, Embracing Nu-Metal's Resurgence

Korn’s appearance was a full-circle moment. The nu-metal pioneers last played Lollapalooza in 1997, when the festival still toured nationally. Nearly three decades later, they returned amid a renewed interest in the genre they helped define. Frontman Jonathan Davis, standing behind his signature mic stand, led the group through a thunderous set that pulled from early records including Issues and their self-titled debut.

Fan favorites like “Freak on a Leash,” “Blind,” and “Here to Stay” hit with full force, while moments like a surprise Metallica riff and a Queen homage added unexpected flair. Before launching into “Y’all Want a Single,” Davis acknowledged the moment: “The fact we’re up on this stage after 28 fucking years? I cannot thank y’all enough.” The crowd answered with raised fists and middle fingers, echoing the rebellious spirit Korn has long embodied.

Bleachers Bring Feel-Good Rock to All Ages

Jack Antonoff’s Bleachers delivered a set steeped in pop-rock nostalgia. Drawing sonic inspiration from Springsteen and visual cues from Americana, the band blended heartfelt storytelling with communal energy. Antonoff invited fans to climb on shoulders during “Rollercoaster” and guided singalongs through “Everybody Lost Somebody” and “Stop Making This Hurt.” At once self-aware and exuberant, the performance leaned into its retro leanings without losing contemporary relevance.

T-Pain Celebrates Two Decades of Hits

T-Pain turned the Bud Light stage into a full-blown celebration. With DJ Montay and dancers backing him, he ran through a hit-heavy set that spanned his career and covered iconic tracks. Highlights included his stripped-down cover of Sam Smith’s “Stay With Me,” along with high-energy versions of “Buy U a Drank” and “I’m Sprung.” His contributions to tracks like Flo Rida’s “Low” reminded audiences of his enduring influence on 21st-century pop and hip-hop.

Djo Returns to His Roots

Djo, the solo project of Stranger Things actor and former Post Animal member Joe Keery, brought a hometown energy to his set. Performing tracks from his latest album The Crux, Djo blended synth-heavy grooves with falsetto vocals and throwback aesthetics. His set honored Chicago roots through visuals, local collaborators like trumpeter Nico Segal, and even a prop modeled after the city’s iconic Cloud Gate sculpture.

Closing with “End of Beginning,” the viral hit that has become Djo’s signature, Keery looked visibly moved. “Feels good to be back in Chicago,” he said, a sentiment the crowd clearly shared.

As Lollapalooza’s second day came to a close, it was clear that the festival continues to thrive on unexpected pairings and generational crossover.