A Definitive Ranking of Every Lollapalooza Lineup from Worst to Best

Editor’s Note: This ranking of every Lollapalooza lineup was originally published in 2019, and we’ll keep updating it as long as the biggest festival in Chicago keeps rocking. Can you guess where this year’s poster falls? It’s hard to believe that, in 1991, Perry Farrell created the festival as a showcase for Jane’s Addiction’s last hurrah. Of course, many things have changed since its initial heyday in the ’90s. In the US, Lolla has grown and evolved drastically from its touring festival roots, having survived a hibernation from 1997 until 2003, in addition to its canceled 2004 installment, and the virtual presentation in 2020 due to the ongoing COVID-19 pandemic (because it was online, that fest is outside the scope of this exercise). Since then, Lollapalooza has settled down in the Windy City, gradually expanding from two to three to four days. (Though, one could argue the fest’s touring spirit lives on through its international counterparts, which have sprung up in Chile, Brazil, Argentina, Germany, and Sweden.) Throughout its history, some of the most iconic acts in music have performed at the festival, from Paul McCartney to Kanye West to Arcade Fire, in addition to up-and-co...