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Rank and File finds us sorting through an exhaustive, comprehensive body of work or collection of pop-culture artifacts. This time, we celebrate the 25th anniversary of Lollapalooza by determining which installment of the festival was the greatest of them all.

The dog days of summer mean that Lollapalooza is just around the corner, and thousands of music fans are about to descend upon Chicago’s Grant Park. It’s hard to believe that 26 years ago 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.

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, and Germany.) 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-coming talent that have since become future can’t-miss attractions everywhere.

In anticipation of this year’s festivities, the likes of which include Chance the Rapper’s big hometown headlining set, we’ve dug back through the archives to take a close look at every lineup in the festival’s storied history (including the canceled 2004 festival, but excluding international editions) and ranked them from worst to best. In devising our list, we took into account artists’ statures the years they performed, their historical relevance looking back now, as well as missed opportunities and what could’ve been better.

So join us on a trip through the past of this iconic festival (and its sweet posters), and let us know in the comments which lineups are your favorite.

–Killian Young
Staff Writer

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