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The 30 most memorable Lollapalooza performances
Tim Mosenfelder/Getty Images

The 30 most memorable Lollapalooza performances

It was the summer of 1991 when Lollapalooza was born. While it started as a haven to promote the blossoming alternative music scene, it also brought together various music genres to open concertgoers' ears and minds.

Lolla has endured a rocky history of controversies, cancellations, poor ticket sales, venue and format changes, international appearances, and even an extended hiatus. Yet, there are performances that we continue to discuss for better or worse.

Here are 30 of the more notable performances listed in chronological order.

 
1 of 30

Jane's Addiction with Ice-T (1991)

Jane's Addiction with Ice-T (1991)
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One of the highlights of any Lollapalooza tour or daily set is the possibility of artists joining other artists on stage. To this day, Ice-T, on the bill with Body Count, and Jane's Addiction together on stage in Year 1 of the event still might be the best live collaboration in Lolla history. It was certainly head-turning since Perry Farrell and Ice-T would cover Sly and the Family Stone's "Don't Call Me N—a, Whitey."

 
2 of 30

Nine Inch Nails (1991)

Nine Inch Nails (1991)
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Another frequent highlight when Lollapalooza was a touring party during the first season was a young, eager, and aggressive Trent Reznor and his Nine Inch Nails. NIN's debut album, Pretty Hate Machine, was a couple of years old, but Reznor did not lack any energy. Even if the set was not particularly good, it was usually memorable — like at the Phoenix area stop in 1991, when the PA system and his equipment didn't jive. Reznor trashed his gear (which was not a shock) and left the stage for the tour bus.

 
3 of 30

Pearl Jam (1992)

Pearl Jam (1992)
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Pearl Jam has been a staple at Lolla over the years, but let's go back to its 1992 maiden tour for some of the band's most notable moments. Specifically, frontman Eddie Vedder's penchant for climbing the stage scaffolding. During one particular show at New York's Jones Beach in 1992, Vedder nearly climbed to the heavens and managed not to break his neck in the process.

 
4 of 30

'Temple of the Dog' (1992)

'Temple of the Dog' (1992)
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Sticking with Pearl Jam. On April 16, 1991, members of the band, along with then-Soundgarden drummer Matt Cameron (before he officially joined Pearl Jam) and late frontman Chris Cornell, released the self-titled Temple of the Dog album as a tribute to fallen friend and Mother Love Bone singer Andrew Wood. With both bands in the '92 Lollapalooza tour, they hit the stage together to perform songs from the record. One of the better performances came during the Phoenix area stop.

 
5 of 30

Rage Against the Machine (1993)

Rage Against the Machine (1993)
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A year prior, Rage ground out a high-octane set on a side stage at the Lolla Southern California stop. In 1993, the band became the talk of the tour as upstart headliners (for most of the runs). RATM took advantage of any chance to preach and pound its sound — much to the delight of crowds who did not know what to expect but soon became true believers of Rage's message and attitude.

 
6 of 30

The Flaming Lips (1994)

The Flaming Lips (1994)
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Unusual happenings among artists have always been a staple of Lolla. One of the more interesting moments came during the 1994 tour stop in the Denver area. Playing one of its better gigs of the run, The Flaming Lips dragged an upright, acoustic piano across a good portion of the lawn to complete the performance and prove why it was one of the more eclectic yet underrated alternative acts of the time.

 
7 of 30

Jesus Lizard (1995)

Jesus Lizard (1995)
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Jesus Lizard frontman David Yow enjoyed drawing attention to himself and his underground alt-rock bandmates. At one particular Lollapalooza '95 performance in Cincinnati with Jesus Lizard, Yow dropped his pants. That certainly drew plenty of attention — from local law enforcement. When the band left the stage following its set, Yow was arrested for indecent exposure. During an interview with The Washington Post, Yow said he was hauled downtown, and "they fined me, I think, like, $250."

 
8 of 30

Pavement (1995)

Pavement (1995)
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David Low's on-stage pants drop was not the only infamous moment from the 1995 tour. During the stop in Charles Town, W.V., Pavement generated some crowd participation. The indie rockers were not entirely on the same page as the edgier hi-fi crowd that was there to mosh. During Pavement's lo-fi daytime set, the crowd started tossing mud and chunks of sod on stage. Then, an unidentified heavier object hit singer Stephen Malkmus in the chest. Guitarist Scott Kannberg was eventually fed up and started flipping off the crowd and mooning them before exiting the stage.

 
9 of 30

Metallica (1996)

Metallica (1996)
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Some consider the 1996 tour to be the moment Lollapalooza jumped the shark. That might be because the tour was no more two years later. Metallica was the headliner, with Soundgarden and the Ramones also on the bill. Some critics considered this lineup too corporate for the spirit of Lolla. Still, Metallica continued its attempt to open the door to new fans. It delivered powerful sets, like this one in Irvine, Calif. The band would resurface to again headline the event in 2015.

 
10 of 30

Jane's Addiction (2003)

Jane's Addiction (2003)
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When Lollapalooza returned from its five-year hiatus, it was a reunion of sorts for Perry Farrell and Jane's Addiction. While the return did not hold the same luster, Farrell back on stage with the guitarist Dave Navarro was usually the highlight of each tour stop — even though a number were canceled due to poor ticket sales that plague the 2003 return of the event.

 
11 of 30

Arcade Fire (2005)

Arcade Fire (2005)
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After the 2004 Lollapalooza tour was canceled, the event was revived in 2005. It found a permanent home at Chicago's Grant Park as an annual weekend festival. While Weezer, The Killers, and Pixies each brought more of a brand name to the party, it was Arcade Fire, which was only one album into what would be a brilliant career, that proved to be the highlight of the entire festival. They were fresh and energetic amid the blistering summer heat along Chicago's lakefront.

 
12 of 30

Kanye West (2006)

Kanye West (2006)
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Kanye would spend more time at Lolla in the coming years, but playing this specific gig in his hometown is one of the most special moments in the festival's history. Cameos on this performance included another Chicago son Common, Twista, and a rising star named Lupe Fiasco, who skateboarded his way onto the stage.

 
13 of 30

Lady Gaga (2007)

Lady Gaga (2007)
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In 2007, Gaga was still a relatively obscure yet promising conceptual artist who delivered one of the more underrated Lolla performances. With an almost burlesque-type feel, Gaga shined during her daytime set on one of Grant Park's smaller stages. For those who witnessed the gig live, it's one of those "I was there" moments.

 
14 of 30

Daft Punk (2007)

Daft Punk (2007)
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Perry Farrell considers this performance to be one of his favorites in the history of Lollapalooza. You can't argue with the man who runs the show. Over the years, Daft Punk has thrived in festival settings around the globe. However, this one still stands out to Farrell, who marveled at the masses bouncing and dancing along to the electronic art spun by Guy-Manuel de Homem-Christo and Thomas Bangalter

 
15 of 30

Radiohead (2008)

Radiohead (2008)
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Radiohead knows how to put on a show and has delivered when asked to provide musical entertainment at a Perry Farrell party. In 2008, the band got some help from a July 4-caliber fireworks display while playing its hit "Fake Plastic Trees." It was a special "experience" moment that festivals like Lollapalooza are capable of providing. 

 
16 of 30

Rage Against the Machine (2008)

Rage Against the Machine (2008)
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It was 15 years after turning heads as one of the stars on the 1993 Lollapalooza tour that Rage Against the Machine was playing a reunion show at the festival. It was a wild and sometimes unruly atmosphere but as energetic and aggressive as we'd expect from the band

 
17 of 30

Dan Deacon (2009)

Dan Deacon (2009)
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As we've seen, the smaller side stages can be the site of some memorable Lollapalooza performances. It's an opportunity for lesser-known artists to shine. That was the case for electronic/pop composer Dan Deacon in '09. His high-energy effort, complete with a bevy of keyboards, some percussionists, and even a horn section, was like glorified street performance. At one point, a massive conga line formed and a collective yoga-like celebration of dance moves.

 
18 of 30

Lady Gaga (2010)

Lady Gaga (2010)
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Only three years removed from her stellar out-of-nowhere, small-stage Lolla set, Lady Gaga was a household name and ready to shine as a festival headliner. Her 2010 performance was a part dance party, part Broadway show, part therapy session, and part love fest for all. If there's an artist made for Lollapalooza, it's Gaga.

 
19 of 30

Mavis Staples (2010)

Mavis Staples (2010)
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As lavish and over-and-the-top (in a good way) as Lady Gaga's 2010 Lolla performance was, the legendary Marvis Staples delivered a straightforward experience that needed no flash to pack the same punch. Staples let her chops lead the way, and the crowd was there to digest every bit of it. The undisputed highlight of the set was her brilliant, gospel-fueled cover of the Band's "The Weight.

 
20 of 30

Foo Fighters (2011)

Foo Fighters (2011)
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The 2011 Chicago event was a bit of a mess. Gate-crashers, fence-jumpers, and heavy rains during the Foos' headlining set. Of course, if any band can make playing in the rain fun, it's Dave Grohl and Co. The Foo Fighters did not let up or cheat the rain-soaked, mud-caked crowd from forgetting about the elements and celebrating the moment with one of the best live acts of all time.

 
21 of 30

Le Butcherettes (2011)

Le Butcherettes (2011)
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Another small-stage standout performance came in 2011 when garage punks Le Butcherettes, led by the versatile guitarist-keyboardist Teri Gender Bender (also known as Teresa Suarez), whipped a decent-sized crowd into a frenzy with its afternoon set. It was the spirited type of effort we've come to appreciate from those under-the-radar bands that use the Lolla stage to break through. Not to mention, Bender might have had one of the hardest-working drummers in the business. So much so that he vomited during the set, then kept playing.

 
22 of 30

deadmau5 (2011)

deadmau5 (2011)
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Another breakout performance at the 2011 Chicago Lolla event came from this mouse-headed, house-master DJ. It's hard to go up against Foo Fighters, but deadmau5 had already built up his impressive following and more than held his own. His heart-thumping, conceptually scintillating set should go down as one of the best electronica/dance performances in the history of the festival.

 
23 of 30

Florence & The Machine (2012)

Florence & The Machine (2012)
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Consistently strong performances are what we get from Florence Welch and her backing Machine. Welch pulled off a completely superb performance at the 2012 Lollapalooza gathering not too long after canceling some shows due to vocal issues, which made this outing even more impressive. She rested enough to deliver one of the weekend's best shows, including the first-ever live rendition of "Breath of Life" from the Snow White and the Huntsman soundtrack.

 
24 of 30

Chance the Rapper (2013)

Chance the Rapper (2013)
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The Chicago-based rapper, who would headline the North American Lolla weekend in 2017, enjoyed his moment in the sun on a smaller stage here in 2013. He was riding high following the release of his Acid Rap mix tape and drew a massive crowd on a smaller stage. The intimacy of the set that drew thousands all worked, as the energy between performer and audience was high enough for Chance to proclaim, "this is the best moment of my life in the world."

 
25 of 30

Kendrick Lamar (2013)

Kendrick Lamar (2013)
Robert Deutsch/USA TODAY

Still basking in the glow of his highly acclaimed Good Kid, M.A.A.D City, Kendrick Lamar was a confident entertainer. Those fortunate enough to catch his set in Chicago at Lollapalooza 2013 are better for it. Lamar didn't pull any punches or veer from the process that was about to make him a full-fledged star. Rappers are made for these moments, and Lamar was at his best.

 
26 of 30

Outkast (2014)

Outkast (2014)
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Outkast's reunion run in 2014 did not get off to a great start. Long-winded shows combined with a visible lack of chemistry between Andre 3000 and Big Boi didn't have many critics believing their Chicago Lolla headlining gig would be any different. However, something clicked, and it was like old times. The pair was in fine form, on top of its game musically, and seemed to enjoy being on stage together. It was a pleasant surprise for those fans who took the opportunity to give Outkast another chance.

 
27 of 30

Paul McCartney (2015)

Paul McCartney (2015)
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Any time any music fan has the chance to see Sir Paul, do it. One of the early purposes of the Lollapalooza concept was to bring together various genres of music and open doors to new fan bases. During the 2010s, Lolla's demographic was getting younger, but McCartney's presence was still a special moment, especially when Alabama Shakes' Brittany Howard lent her massive talent on a stellar live version of "Get Back."

 
28 of 30

LCD Soundsystem (2016)

LCD Soundsystem (2016)
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Some critics and fans felt LCD Soundsystem's 2007 performance at Lollapalooza outshined the set of headliner Daft Punk. That might have been the case, but James Murphy and Co. were arguably the best of the bunch when the band reunited to headline the 2016 event in Chicago. There almost seemed like a renewed sense of purpose for the group, which was one of the great live acts of the last decade-plus.

 
29 of 30

Tove Lo (2017)

Tove Lo (2017)
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The aforementioned Arcade Fire returned to deliver a serviceable set on the final night of the 2017 event. However, a show-stealer came two sets prior from this gritty Swedish popster. Lo, a few months away from dropping her third album Blue Lips, celebrated her free-spirited nature with hits like "Habits (Stay High)." Yet, the most memorable moment of her gig came during "Talking Body." Lo flashed the building crowd, sending that portion of Grant Park into a frenzy.

 
30 of 30

Bruno Mars (2018)

Bruno Mars (2018)
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Sporting his Chicago Bulls gear, Mars delivered a highly entertaining set while headlining Day 2. Mars is one of the few performers who can make a high-spirited, big-number production succeed, whether in a stadium or the often unpredictable setting of a massive outdoor festival such as Lollapalooza. He knew the crowd was there to have a good time, and he ensured they did

A Chicago native, Jeff Mezydlo has professionally written about sports, entertainment and pop culture for nearly 30 years. If he could do it again, he'd attend Degrassi Junior High, Ampipe High and Grand Lakes University.

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