Lollapalooza at 20: Chicago reporter reflects on iconic moments, wild weather and rising stars

Chicago reporter on 20 years of capturing Lollapalooza | ChicagoNOW

This guest has had a front row pass to Lollapalooza the last 20 years. Selena Fragassi is a Chicago-based reporter who has been attending and/or covering the festival since it found a home in the city after years as a traveling festival. She joins us to tell us about her experience.

CHICAGO - As Lollapalooza gears up for another high-energy weekend in Grant Park, one longtime festival observer has seen it all. 

Selena Fragassi, a reporter with the Chicago Sun-Times, has been covering Lollapalooza since 2009, when the festival was just beginning to grow into the massive cultural event it is today. 

The backstory:

Though she first attended as a fan in 2007, her professional work documenting the festival spans nearly two decades of change, expansion and iconic moments.

"This year is 20 years it's been in Chicago. And that first year it was $125 for the weekend. There was 66,000 people, which if you consider, there is like a quarter million now. There was only five stages. So it's very different," said Fragassi. "It's doubled or tripled in attendance and stages and bands. You have the Perry stage now, which is a whole thing in itself where people just market if they like EDM."

Among the most memorable moments she’s witnessed was Jared Leto’s dramatic stunt during a 30 Seconds to Mars performance, when he appeared to leap from the roof of the stage into the crowd.

Another standout came in 2021, as the city emerged from pandemic restrictions. 

The band Black Pumas performed their song "Colors," a unifying anthem introduced by then-Mayor Lori Lightfoot. Fragassi called it a moving experience after a long stretch without live music.

Emerging Talent:

Fragassi also praised Lollapalooza’s unique ability to blend global superstars with emerging talent. 

From early-career sets by Lady Gaga and Chance the Rapper at the BMI stage to breakout performances like Chapel Roan’s record-breaking crowd in 2023, she emphasized the festival’s power to launch careers in real time. 

"You never know where you're gonna catch the artist in their career cycle," said Fragassi.

Weather has often been a wildcard at the summer event, from heatwaves to downpours. 

Fragassi recalled the 2011 storm during Foo Fighters’ set that tore up Grant Park and caused a million dollars in damage, which the festival covered.

Despite the unpredictability, she credits organizers with solid safety planning and efficient communication.

What You Should Know:

For festivalgoers, Fragassi recommends dressing in layers and arriving early to catch smaller acts that may become headliners in future years. 

"I think you want to go for the headliners. You love Olivia. You love Sabrina. But you've got to go to the early acts. They're going to be the headliners at some point in the future. You're going to catch them early. You're gonna see someone who's going to surprise you," said Fragassi.

Food, she added, is also a draw. Much like Taste of Chicago, the festival features dozens of local vendors, including iconic names like Rainbow Cone, Billy Goat Tavern and Connie’s Pizza.

This year, Fragassi is especially excited for the female-heavy headliner lineup, including Olivia Rodrigo and Sabrina Carpenter, and says she's keeping an eye on rising acts like Doechii and UK-based Wonderhorse.