Lollapalooza started life in 1991 as a travelling farewell tour for Jane's Addiction, dreamt up by frontman Perry Farrell — and accidentally became the template for the modern American festival. After the touring era wound down in the late 90s and a couple of false restarts, it settled into Grant Park, Chicago in 2005, expanding to a four-day event in 2016.
The gap in the posters below is real: there was no Lollapalooza between 1998 and 2002, and the 2004 edition was cancelled. Everything since 2005 is the Chicago era — and the shift in the posters from hand-drawn alternative-era artwork to stacked modern festival typography tells the story of the industry as much as the festival.