I love Lollapalooza. I have since day one back in 1991. In fact, with the exception of one dark summer, I’ve been to every Lolla. EVER. And, as a former Chicagoan, I especially love that Lolla has posted up on the lake in my former hometown since 2005. With this year’s fest about to kick off — touting anticipated sets from Lorde, Eminem, Kings of Leon, Skrillex, OutKast and about 95 others — I thought it might be a good time to look back at 21 times Lollapalooza broke our brains over the past decade.
1. O-o-o-Orwells (2013)
The Chi-town boys were just starting to make noise a year ago, but they definitely made a splash when singer Mario Cuomo allegedly exposed himself during an encore of the Stooges’ “I Wanna Be Your Dog.”
2. Kendrick Lamar Helps Out A Good K.I.D. (2013)
Compton’s best is focused on getting every ticket holder the best view possible. Need proof? Check out the time he stopped his set to help a wheelchair-bound superfan get to the front row.
3. Phoenix Singer Takes The Long Way (2013)
Near the end of their headlining set, Phoenix singer Thomas Mars sprinted out to the soundboard and then crowd surfed his way back to the stage.
4. Avicii’s Giant Skull (2012)
If you’re a superstar DJ, you don’t just show up with a couple of turntables. No, you bring a giant, super-scary skull.
5. Die Antwoord Get Super Freaky (2012)
The South African rap duo did not hold back one bit during their super-hyped set.
7. Jack White Doubles Down (2011)
Because he’s insatiable, the former White Stripes frontman made his solo debut at the fest with not one, but two bands: the all-male Buzzards and the all-female Peacocks.
What’s a festival without some extreme weather? Nothing stops Dave Grohl and company.
Four years after making her debut on a small side stage, Gaga returned a champ and, wearing fishnets and some electrical tape, crowd surfed during a set by her bests in Semi-Precious Weapons.
10. Green Day Make This Kid’s Day (2010)
Billie Joe Armstrong had no idea what he was in for when he invited a fan to come up and sing “Longview” during the band’s headline set. He did not see that mouth kiss coming.
11. Vic Mensa Was Dying To Get In (2010)
Chi-Town rapper Mensa recently told MTV News about the time he hopped the fence to see J. Cole on the first day of that year’s festival and then tried to sneak a foreign exchange student he was crushing on into Lolla, only to figure out that security had been upped. “She’s gonna be lost all night it’s gonna be my fault,” he fretted. So, the former wall-climbing graffiti artist tried to scale a Metra train bridge and hit a transformer with 15,000 volts running through it and fell to the ground. Long story short: he got arrested and ended up in the hospital, where his Spanish crush came to visit, but his girlfriend didn’t. Doh!
12. Yeah Yeah Yeahs Step In For Beastie Boys (2009)
When Beastie Boys member Adam Yauch had to bow out due to his (ultimately fatal) battle with cancer, Karen O and band stepped in for a thrilling, colorful set that gave the night’s other headliners, Tool, a run for their money.
13. Kanye West Comes Home Again (2008)
Ye’s second time around at Lolla was special, not just because it was in his hometown, but because it gave him a chance to pay homage to his recently departed mother, Donda.
14. Rage Against The Machine Make The Earth Quake (2008)
I was as jacked as anyone to see RATM storm back from a hiatus for a headlining slot at the festival they first played in 1992. They kept their clothes on this time, but their stomp rock got the crowd so hyped the band had to stop the show several times to make sure everyone was safe.
15. Lupe Flips Out (2008)
If I hadn’t seen it with my own eyes I wouldn’t have believed it, but hometown rapper Lupe Fiasco stunned the crowd during a daytime set with a perfectly executed back flip. Without interrupting his flow at all.
16. Iggy Pop Has Lots Of Fun (2007)
Never let it be said that punk godfather Iggy Pop is “No Fun.” In fact, when his reunited band the Stooges played the fest for the first time they invited a few fans up to celebrate. They probably weren’t expecting that many.
17. Daft Punk Own The Night (2007)
When a pair of robots show up with a giant glowing pyramid, we all win.
18. Amy Winehouse Won Our Hearts (2007)
With her towering signature beehive holding up under the withering heat, the sometimes erratic Winehouse shut up the haters with a killer set backed by her smoking hot band.
19. Jared Leto Gets Super High (2006)
Before Thirty Seconds to Mars blew up into global superstars, they were still the actor/singer Leto’s side project during movie hiatuses. This is a perfect example of why they’re not anymore.