The original alt-rock festival began as an all-stops-out farewell tour for Jane’s Addiction, but frontman and festival architect Perry Farrell was eager to grant it a life of its own. In over two decades since that first 1991 tour, Lollapalooza has produced brilliant, disappointing, bizarre, and disastrous performances.

We can only hope that this year, with a 140-artist lineup featuring everyone from lovable bassist Paul McCartney to metal vets Metallica to electronica-jazz futurist Flying Lotus, will be no different. To celebrate the history of this great festival, here, in chronological order, are 20 of the most exciting, most important, and weirdest Lollapalooza performances, or – if you prefer – just the ones it’s easiest to wish you were there for.

Body Count, 1991

The inaugural Lollapalooza’s architects might have imagined Ice-T as the new festival’s rapper-in-residence, but the Original Gangsta showed up as a rock star. Leading his hurtling thrash-metal band Body Count through lightning-rod single “Cop Killer,” he strutted and headbanged like a pro. Dueting with Perry Farrell on a tense, crawling version of Sly and the Family Stone’s “Don’t Call Me N*gger, Whitey” – introduced nightly by a mortifying joke from Farrell and a deeply unamused entrance from Ice – he was the grave and formidable counter to the Lollapalooza impresario’s faux-fascist hysteria.

Whatever your reaction to the pair’s uncomfortable racial theater, they made clear that the festival aspired to more than untroubled entertainment for the motley rock-kid horde: It wanted friction.

Nine Inch Nails, 1991

Trent Reznor took the Lollapalooza stage soaking wet and covered in white powder, to scream his way through Nine Inch Nails‘ enveloping industrial catharsis. At an infamous July 18 show, the band stopped-and-started a set so many times at the mercy of a doggedly faulty power setup it gave up, smashed its synthesizers, and retreated. “Everybody on the stage would be all caked up in powder and water and he would be destroying his equipment,” Perry Farrell reminisced to Esquire years later. “Those were the good ol’ days, you know?”

Jane’s Addiction, 1991

Lollapalooza’s first year would be its exhausted hosts’ final tour until 1997, and their shows offered the unusual spectacle of a band that was in the final stages of implosion even as the circus it was leading made it bigger than it had ever been. Despite increasingly bad blood between Farrell and Dave Navarro, the band remained on the tour, playing blistering sets near the end of each day’s show.

The Jim Rose Circus Sideshow, 1992

“The kids used to faint,” Jim Rose recalled in a 2003 issue of SPIN. An incomplete list of attractions offered by the Jim Rose Circus Sideshow, who had found it “very difficult to get a gig in the U.S.” before being recruited by Perry Farrell for the counterculture’s biggest traveling circus: a guy who snorted a condom through his nose and retrieved it from the back of his throat; a guy who lifted “incredible amounts of weight” with an alarming series of extremities; a guy (“Zamora The Torture King”) who ate light bulbs; and a collection of 1992’s hottest alternative artists competing to see who could drink the most “bile beer,” a beverage pre-digested by, then pumped from the stomach of, a man called The Tube. Eddie Vedder won.

Pearl Jam, 1992

In the summer of 1992, Pearl Jam’s debut album Ten had been out for almost a full year, but had only just cracked the Billboard top 10. By the beginning of 1993, it would be selling better than Nirvana’s already-totemic Nevermind. In between, there was Lollapalooza, where a young, scrappy, and sixth-billed Pearl Jam delivered a series of fiery performances that immersed a boyish Eddie Vedder’s ecstatic growls in a perfectly grunge-y soup of clattering drums and squirting guitar.

Primus, 1993

“At the time,” Primus frontman Les Claypool explained in Greg Prato’s oral history Primus, Over the Electric Grapevine, “people were like, ‘What the hell is this?'” The band that proved there was such a thing as slacker prog headlined one of the less star-powered Lollapalooza lineups (Fishbone, Arrested Development, a not-yet-big Tool) — but the 1993 festival’s relative modesty, and its artists’ camaraderie, lent the music a warm, collaborative glow: Fishbone saxophonist Angelo Moore remembers jamming with Primus on “Here Come The Bastards” as “the brightest moment.”

Smashing Pumpkins, Second Stage 1994

Smashing Pumpkins headlined Lollapalooza 1994 under the worst possible circumstances: as last-minute substitutions for Nirvana, who cancelled just a few days before Kurt Cobain’s body was found. Audiences weren’t always friendly; songs weren’t always well-received; in Philadelphia and New York, the Pumpkins ceded part of their set time to Courtney Love. But in late August, the band slipped out from under its accidental-headliner yoke to play three confident, intimate, and totally unexpected shows from the festival’s second stage: a few snatched hours of freedom.

Breeders, 1994Lollapalooza Poster 94

“Virtually perfect,” the New York Times called them, singling out no other band for more praise in a lineup that Smashing Pumpkins’ James Iha would call “one of the coolest bills I’ve ever played on.” The Breeders’ supple, wry indie rock would indeed have been a perfect, modest, hazy tonic in the summer heat.

Flaming Lips, 1994

The sweet-toothed psych-rockers weren’t always so cuddly. Their performances from Lollapalooza ’94’s second stage are a squall of gorgeous noise. Wayne Coyne is a staggering, twitching weirdo instead of a beatific showman. But when he leans into the mic for a high note and his face briefly contorts into involuntary bliss, you can see the shadow of the earnest, perpetually childlike rock star he’d become.

George Clinton, 1994

Accompanied by at least a score of singers, musicians, and extras, the Godfather of Funk condensed his band’s sprawling roil into dense 45-minute sets that stirred Parliament-Funkadelic tracks old and new into a thick, psychedelic brew. The festival also gifted us the weird spectacle of Billy Corgan interviewing George Clinton.


(A Tribe Called Quest, Beastie Boys, Cypress Hill)

Ice-T’s rock-star turn aside, the original Lollapalooza was never the ideal hip-hop festival — it mostly hewed to an alt-rock vision of the world. But the festival was beastie boys lollapalooza 94nothing if not curious and ambitious. The near-flawless rock lineup of 1994’s incarnation stood alongside a solid rap bench led by main-stage performances from ’80s veterans A Tribe Called Quest and Beastie Boys, and a regular but brief second-stage appearance from triple-platinum “Insane in the Brain” rappers Cypress Hill. A restless rap head, marooned amidst Lollapalooza’s guitar heroics, would have been able to cobble together a perfectly respectable day.

Pavement, 1995

This was Lollapalooza’s Dylan-at-Newport moment. Amid the fractured, depressed post-Nirvana landscape, on a tour Sonic Youth’s Lee Ranaldo would later claim “killed Lollapalooza,” Pavement’s arch, sloppy approach to rock ‘n’ roll got the indie rockers pelted with mud and boos by an offended crowd. The raw punk intimacy of Nirvana; the intricate glam bombast of Smashing Pumpkins (who, legend has it, insisted Pavement be kept off the 1994 lineup); even the warm indie-rock glow of bands like The Breeders — none of it had prepared that West Virginia audience for Stephen Malkmus and company’s unapologetic Slack.

DEVO, 1996

Lollapalooza’s sixth year would become its famous worst. Metallica’s sheer fame and colossal fanbase would make them the tour’s most controversial headliner ever. (Perry Farrell would leave both the tour and the William Morris Agency over the booking, turning his attention to his impeccably alt but never successful ENIT Festival.) A year later, Lollapalooza would anxiously gather together a clutch of electronic artists, to shepherd it into the future; a year after that, the festival would be on apparently permanent hiatus. But even as the tour lost its way, its uncertainty enabled new, weird opportunities: Maybe only in 1996 could Lollapalooza have hosted the comeback of sui generis New Wave pranksters DEVO, and definitely only in 1996 could you have seen sui generis New Wave pranksters DEVO open for Metallica. In tight, muscular form, the band rendered its early-’80s back catalogue as bouncing, yelping pop-punk — as clear a bridge as Lollapalooza ever built between undergrounds past and present.

Wilco, 2006

By the time Wilco headlined Lollapalooza, the festival had given up its wandering to settle down in Grant Park in Chicago, which made Jeff Tweedy’s expert indie-rock troubadours hometown heroes. Bearded and relaxed, Tweedy led the band through a gorgeous sunset show, lingering generously over old favorites and debuting a few new ones — including “Impossible Germany,” which would become a highlight of Wilco’s live album Kicking Television.

Sleater-Kinney, 2006

Before the announcement of two farewell gigs in their hometown of Portland (and long before their 2014 reunion), this was Sleater-Kinney’s last scheduled show. The indie-rock heirs to The Who concentrated on their final pre-breakup album The Woods. Corin Tucker and Carrie Brownstein’s double-helix voices wrapped themselves in colossal sheets of guitar cascading over the festival crowd. Though Sleater-Kinney, like Sherlock Holmes, eventually took mercy and returned, the threat of their permanent disappearance made this one of the most essential Lollapalooza shows ever.

Broken Social Scene, 2006

When the motley and gargantuan Canadian indie-rock collective reached the end of their brief Grant Park set, an audienceBroken Social Scene Lollapalooza 2006 blissed out on their eclectic, clattering rush cheered for more. When the Red Hot Chili Peppers arrived to take the stage, and found themselves in a brief standoff – not only with the sprawl of Broken Social Scene itself but a minor sea of old fans and new converts – it was a crystallized Lollapalooza moment: a spontaneous collision between different bands, different eras, and different ideas of Alternative. Broken Social Scene eventually yielded without performing an encore; their replacements took the stage to scattered chants of “f*ck the Peppers.”

Daft Punk, 2007

Yes, this is the one with the pyramid. Daft Punk’s triumphant inauguration of the resurrected Lollapalooza’s third year in Grant Park brought Chicago audiences the meticulous, overwhelming spectacle the French house robots had debuted at Coachella in 2006 and would permanently enshrine in November’s Alive 2007. Farrell reported admiringly on the show to Esquire: “It sounded like they were doing a set of glitched beats, [but] they were blowing the speakers out one by one.”

Arcade Fire, 2010

Arcade Fire had still been a young band when they joined their first Lollapalooza in 2005, where they discovered that their jubilant, cathartic, maximalist indie rock was capable of sending festival crowds into ecstasy. When they returned as headliners five years later, it was as something strangely close to the biggest band in the world. This time the band didn’t need to lead its audience to rapture — anticipation had already put them there. The older Arcade Fire’s fatter, deeper catalogue served it well; they closed out the 2010 festival with a long, rich, vivid tent-revival set that sent their new congregation home in bliss.