Which alternative rock band headlined the first Lollapalooza festival in 1991?

Jane’s Addiction headlined the first Lollapalooza festival in 1991.

Lollapalooza began in July 1991 as a farewell tour for Jane’s Addiction, organized by the band’s singer Perry Farrell. The touring festival presented alternative rock alongside punk, metal, rap, and performance art, making it different from a conventional single-genre concert series.

The inaugural lineup included Jane’s Addiction, Nine Inch Nails, Ice-T, Living Colour, Siouxsie and the Banshees, and Butthole Surfers. Jane’s Addiction served as the central act because the event was created around the group’s final tour at that time.

Lollapalooza later became an annual festival rather than a farewell tour and eventually established a permanent home in Chicago. Jane’s Addiction is therefore the answer to the inaugural-headliner question, not a later festival headliner such as Radiohead, who played the event in 1996.