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. It’s hard to believe that, in 1991, Perry Farrell created the festival as a showcase for Jane’s Addiction’s last hurrah. Since then, Lollapalooza has settled down in the Windy City, gradually expanding from two to three to four days. AdvertisementAhead of this year’s festivities, 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. So join us on a trip through the past of this iconic festival (and its sweet posters), and let us know which lineups are your favorite.