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10 Legendary Lollapalooza Sets Through the Years

From Amy Winehouse's pre-rehab gig to Daft Punk's pyramid, these are some of the biggest performances in the festival's history

1 / 10

Rage Against the Machine: July 18, 1992, Philadelphia

Pissed off by Tipper Gore’s infamous Parents Music Resource Center pushing for music to be labeled “Parental Advisory,” Rage protested this censorship loud and clear in Philly on the Lollapalooza 1993 tour. They stood totally naked onstage for 15 minutes, with the letters P M R C spelled out across their four chests, and black duct tape over their mouths. They made the biggest statement of all by being seen and not heard. –Jessica Letkemann

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2 / 10

Pearl Jam: August 29, 1992, Wisconsin

For their headlining set in 2007, repeat performers Pearl Jam turned in a grand rock-out through a decade and a half of their finest jams that culminated with a stageful of friends and crew (including frontman and Chicago-native Eddie Vedder riding atop former Chicago Bull Dennis Rodman’s shoulders). 

But further back in the mists of time, when their first hits—“Alive,” “Even Flow” and “Jeremy”—were just becoming ubiquitous, the Seattle band pulled off a literally death-defying set at Wisconsin’s Alpine Valley in the summer of 1992. In the early afternoon, Vedder left the audience of 40,000 dumbfounded when he went into the crowd during “Porch,” climbed a pillar supporting the amphitheater’s roof, found a rope, and dropped himself into the writhing pit on the lawn, beginning at 33:24 in the video above. –Jessica Letkemann

3 / 10

Amy Winehouse: August 5, 2007, Grant Park, Chicago

Amy Winehouse only performed at Lollapalooza once in her curtailed career—an unfortunate fact for a variety of reasons, perhaps chief among them that her performance wasn't the test-of-time triumph one might have anticipated. Minus the later context, it might have been nothing more than a standard festival performance, Winehouse seemingly teetering into boredom and disinterest despite technical proficiency. But shortly after she played "Rehab," with its now-famous defiant stance on the treatment, Winehouse indeed checked herself in for help, canceling multiple shows that month and even being hospitalized for a multiple drug overdose. To that end, her 2007 Lolla set is the precipice before the descent into the Winehouse American audiences came to know via the tabloids. –Kevin Rutherford

4 / 10

Daft Punk: August 3, 2007, Grant Park, Chicago

Long live the pyramid. These days, unique contraptions out of which DJs and producers dispense their bass-shaking material may not be as rare—most recently, Deadmau5 has made sure of that—but when Daft Punk rolled in to Lollapalooza 2007 from within a giant LED pyramid, it was damn near otherworldly, and not just because the sounds came from two dudes dressed as robots. From the intermittent, regurgitating first sounds seemingly out of some sort of distorted dial-up internet nightmare to a rousing rendition of "One More Time," Daft Punk manipulated their way through hits new and old, remixing and reworking to create a mix for the ages, with a killer light show to boot. –Kevin Rutherford

5 / 10

Kanye West: August 3, 2008, Grant Park, Chicago

Just a year before 'Ye's stand, Daft Punk regaled the Lollapalooza audience with an unforgettable light show. They were there again in 2008, if only in spirit—and the dazzling twirl of lights and lasers continued on thanks to Kanye West. In the midst of a victory lap following 2007's Graduation, Yeezus descended upon his hometown fest for the second time as part of his Glow in the Dark Tour. Even from afar one could see West, lit up against the glittering backdrop by his glowing coat and iconic Shutter Shades. Cuts like "Homecoming" hit harder—and not just because of the location—and when he performed "Hey Mama" in tribute to the "woman who drove me to Chicago at the age of three," the rowdy crowd was deftly attentive. Oh, and how did Daft Punk fit in? Let's just say the rendition of "Stronger," then still a relatively new song, was one that'll live forever. –Kevin Rutherford

6 / 10

Green Day: August 7, 2010, Grant Park, Chicago

Lolla headliners typically turn in tailored two-hour sets, but Green Day blew way past that mark with a hyperactive bonanza of what-will-happen-next surprise and delight. Gunning their engines through all kinds of musical goodies from every corner of their career (“When I Come Around” to “21st Century Breakdown”), the trio’s headlining set packed stage-divers, feather boas for a medley of great covers like “(I Can’t Get No) Satisfaction” and — hitting everyone right in the feels — a guy fan who kissed Billie Joe after being invited to duet on “Longview” and being handed the frontman’s guitar. Even the actual fireworks that bloomed in the sky during the set couldn’t out-dazzle that moment. –Jessica Letkemann

7 / 10

Lady Gaga & Semi Precious Weapons: August 6, 2010, Grant Park, Chicago

Remember Semi Precious Weapons? It's cool if you don't—you're not alone—but for a brief time in 2010, all eyes were on them, thanks to a high profile co-sign from Lady Gaga. That came to a head during the band's Lollapalooza set that year, which featured Gaga in a contributing role—that is, she contributed some epic stage dives to the proceedings, wearing nothing but fishnets. Frontman Justin Tranter even dispensed this hot take: After announcing he'd kill anyone who called Lady Gaga a pop star, he declared that "Semi Precious Weapons and Lady Gaga proved at Lollapalooza 2010 that rock 'n' roll is fucking back." –Kevin Rutherford

8 / 10

Foo Fighters: August 7, 2011, Grant Park, Chicago

Is it a festival if it doesn't rain? It's certainly a question worth asking, despite most folks' inclination to remain snug and dry during an outdoor set. There comes a point in time where one passes the threshold for wetness and amounts of mud caked to one's body, and the crowd that attended the Foo Fighters' rollicking 2011 Lollapalooza set had long conquered it—a welcome sight, certainly, to frontman Dave Grohl, who played along by getting absolutely soaked to the bone himself. There are moments—take the downpour-aided performance of "My Hero," for instance, that appear to be sheer bliss, rain and all. –Kevin Rutherford

9 / 10

Kendrick Lamar: August 3, 2013, Grant Park, Chicago

By the time Kendrick Lamar hit the Lollapalooza stage in 2013 for the first—and so far only—time, he still had something to prove. Sure, good kid, m.A.A.d. city had dominated rap circles since the previous October, but here was his chance to connect with perhaps his biggest audience yet—and the festivities got so wild, he even incited a pair of wheelchair-bound attendees to crowd surf all the way to the barricade. After admiring their tenacity, Lamar informed the audience that they had now reached a 10 on the ambiguous system that measures the success of festival performances, but now he was "looking to take this shit to a motherfucking 15." He segued into "m.A.A.d. city," and the "perfect 10" crowd reacted appropriately. "15" may have even been underselling it. –Kevin Rutherford

10 / 10

Rihanna with Eminem: August 1, 2014, Grant Park, Chicago

She wasn't on the lineup, but you just had to know she'd show up. Days before their collaborative tour kicked off, Eminem headlined Lollapalooza with a massive 31-song set, punctuated about midway through by a fairly unsurprising but nonetheless welcomed cameo from tourmate Rihanna. We had to hear "Love the Way You Lie"; his set would be criminal without. And "The Monster," then the duo's newest collaborative hit? Yeah, absolutely. But it was when Rihanna became Dido for a few minutes, taking over the hook on "Stan," that hype for the subsequent tour went into overdrive. It was a duet that continued on tour, but nothing could quite top the magic of the first time. –Kevin Rutherford

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