On the second day of Lollapalooza on Friday, there was a magical aura in the air throughout Grant Park in Chicago.

It started early in the day, with a string of standout performances and continued into the evening with a trio of sets bouncing between the T-Mobile stage and Lakeshore stage. While there were certainly a number of great artists playing all day, there were six which truly caught our attention in such a special way. 

Gigi Perez

Early on, Gigi Perez quickly emerged as one of the best, drawing a large crowd to the T-Mobile stage. For a festival littered with young, twenty-somethings showcasing their carefully coordinated outfits trying to impress or keep up with their friends, Perez offered a sense of earnestness in her performance. Her vocals were gorgeous, not pretentious, not flamboyant, but certainly remarkable, as she weaved effortlessly from rock to pop to folk to breathtaking ballad, including a cameo from her sister Bella. 

It's worth noting, the day before, Alex Warren brought out Perez to join him on stage and mentioned he had a chance to spend time with her family. And when Bella left the microphone, she hugged Gigi and went to stand in front of the stage alongside her family, who seemed visibly proud to be watching Gigi. The singer herself also paused multiple times during her set, telling the crowd she just needed a moment to take it all in—the crowd size and the fact that she was playing Lollapalooza.

Del Water Gap

Samuel Holden Jaffe (aka Del Water Gap) has long been a Variance favorite, and his performance Friday afternoon on the Tito's Handmade Vodka stage further proved why. He was practically floating on stage at times, delivering a handful of fan favorites, capped by his songs "All We Ever Do Is Talk" and "Perfume," both of which ignited a jolt of electricity into the crowd. He also mentioned during his set that some of his songs were inspired by his experience nearly having a mental breakdown. But he assured the audience it's OK because he is in therapy now, encouraging his fans to also seek therapy for their own mental health. It was a moment of transparency and candor that transcended the music.

T-Pain

Speaking of transcending, if there was one afternoon performer who very well could have been a headliner, it was none other than T-Pain, who attracted an incredible crowd to the Bud Light stage (larger than Luke Combs the night before and Korn's eventual headlining slot a few hours later on Friday night). As he appeared on stage, the energy across the field quickly elevated, as people across generations sang along with the Tallahassee rapper. If you were looking for fun, exciting, no-drama performances at Lolla on Friday, T-Pain's was an absolute highlight.

Djo

Later in the afternoon, actor-musician Joe Keery, who performs music as Djo, celebrated his homecoming with an hourlong love letter to the city he once called home, as he lived in Chicago for six years while he went to school and sometime afterward. "To be playing on this stage with you people means the world to me," Keery told the crowd, eventually leading into the gem that is "End of Beginning," which literally captures his feelings of the time when he left Chicago to pursue acting in Los Angeles.

The song was introduced by a montage of home videos and cell phone footage. "Without you, this song wouldn't be possible," he said as he began to play. It was such a tender moment. "And when I'm back in Chicago, I feel it," the lyrics go. "Another version of me, I was in it / I wave goodbye to the end of beginning." In the bridge, he declares: "You take the man out of the city, not the city out the man." 

It was beautiful. And the crowd made sure to send all that love back to him.

Wallows

Leading up to the grand finale, Wallows (made up of Dylan Minnette, Braeden Lemasters and Cole Preston) took over the Lakeshore stage to close it out for the night. It was the perfect bridge from Djo to Olivia Rodrigo, as many from the T-Mobile crowd migrated over to watch Wallows. And the trio was sure to make the most of their hour set, quickly launching into "Your Apartment" as enthusiastic fans sang along.

It was noteworthy how Wallows artfully played both to their own dedicated fanbase (of which there were many) and appealed to the crowd gathered at nearby T-Mobile waiting for Rodrigo. Multiple times throughout their set, they asked if fans were excited to see Olivia and noted they would also be watching her. After playing their song "Are You Bored Yet?" with about 10 minutes left until Rodrigo's scheduled start time, they then essentially released the crowd as they played "I'm Full," telling the audience they were giving them one more song "as you walk over to Olivia."

Olivia Rodrigo

Then it was time for the star of the night herself, as Olivia Rodrigo emerged literally from darkness, appearing suddenly on stage, drenched in red lighting as she opened with "obsessed." For a singer who's a mere 22 years old, it was surely a big lift to be the headliner of such a marquee festival, just two albums into her career. And while there was certainly debate about whether this was a smart pick, Rodrigo held her own and made a clear case as to why she deserved to be top-lining Lollapalooza.

With an epic, 20-song set list, Rodrigo proved she has a wealth of songs to choose from, including such standouts as "vampire," "drivers license," "traitor," "bad idea right?," "deja vu," "brutal" and "good 4 u." To top it off, she brought out a special guest, Rivers Cuomo of Weezer, which was a perfect pairing as the duo sang Weezer's "Buddy Holly" and "Say It Ain't So." It's become a tradition for Rodrigo to bring out guests such as David Byrne of Talking Heads at Governors Ball and Robert Smith of The Cure at Glastonbury. And it's proof not only that Rodrigo knows how to put on a show, but it showcases her true appreciation for a wide spectrum of music and genres.

So yes, Olivia Rodrigo might be early in her career. But she definitely filled the role of headliner very well. And it was truly one magical night.