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Ranking every Lollapalooza lineup from 2005 to today

Ten years ago, Lollapalooza settled in Chicago. Over the past decade, there have been many headliners, storms and surprises. Which year ranks as the best?

Written by
Brent DiCrescenzo

After starting out as a touring carnival in 1991 and redefining the American festival, Lollapalooza grew up and settled down in 2005, planting its roots in Chicago. In the decade since, the summer music festival has expanded, from two days to three, and from half of Grant Park to all of Grant Park. Over those ten years, DJs have infiltrated the bills, bringing some nightclub energy to an event that really, really loves to book the Black Keys, Jack White and My Morning Jacket (count 'em up below).

Considering that Lollapalooza is hitting its diamond anniversary with our city, it's time to look back through the highs and lows and rank every Lollapalooza in Chicago. No, we're not counting the touring '90s ones, because those were obviously cooler.

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Lollapalooza 2014

10. Lollapalooza 2014

Headliners: Eminem, Kings of Leon, Outkast, Skrillex, Arctic Monkeys, Calvin Harris

Also: Lorde, Spoon, Gambino, Foster the People, Avett Brothers, Lykke Li, Broken Bells, CHVRCHES, Bleachers, Cut Copy, Phantogram, Krewella, Zedd, Iggy Azalea, Run the Jewels, Cage the Elephant

Lamest act: The Airborne Toxic Event

Could have seen 'em before they blew up: Hozier, Royal Blood

Last year was the first we began asking the question: Do headliners matter? An uninspiring mix of repeat visitors and bands common to most other festivals, Lollapalooza 2014 sunk spirits even further in its mud pits. Add in record, stifling crowds and a nasty assault on Blood Orange and you have a year to forget.

Lollapalooza 2013

9. Lollapalooza 2013

Headliners: Mumford & Sons, The Killers, NIN, The Cure, The Postal Service, Phoenix

Also: Kendrick Lamar, Vampire Weekend, the National, Lana Del Rey, Alt-J, Beach House, Hot Chip, Imagine Dragons, Grizzly Bear, Tegan & Sara, 2 Chainz, Cat Power, Ellie Goulding, Queens of the Stone Age, Steve Aoki

Lamest act: Imagine Dragons

Could have seen 'em before they blew up: Haim, Chance the Rapper

Could have seen 'em before they ended: Crystal Castles

It does not bode well for the future that the two most recent lineups are dwelling in the cellar. This was the year of cancellation, with Death Grips and Azealia Banks pulling out late. Thankfully, the spirits pulled the plug on Imagine Dragons, who shorted out their stage. In hindsight, Kendrick Lamar and Alt-J outdrew some headliners.

Lollapalooza 2011

8. Lollapalooza 2011

Headliners: Foo Fighters, Eminem, Muse, Coldplay, My Morning Jacket, Deadmau5

Also: Ratatat, Lykke Li, Explosions in the Sky, Arctic Monkeys, CeeLo Green, A Perfect Circle, Crystal Castles, Bright Eyes, Nas, Death from Above 1979, Foster the People

Lamest acts: The Pretty Reckless, Patrick Stump

Could have seen 'em before they blew up: Walk the Moon, Ellie Goulding

Could have seen 'em before they ended: CeeLo Green, Ween

Okay, CeeLo, being a person, can't technically break up, but his career is toast nonetheless. Looking over that litany of aggro rock acts, it was a pretty dude-heavy bill. Hopefully, Lolla got the memo that women buy more tickets to festivals now.

Lollapalooza 2009

7. Lollapalooza 2009

Headliners: Depeche Mode, Tool, The Killers, Kings of Leon, Jane’s Addiction, Yeah Yeah Yeahs

Also: Snoop Dogg, TV on the Radio, Animal Collective, the Decemberists, Arctic Monkeys, Passion Pit, Lykke Li, Andrew Bird, Dan Auerbach, Fleet Foxes, Andrew Bird, Vampire Weekend, Rise Against

Lamest acts: thenewno2, Asher Roth

Could have seen 'em before they blew up: Bon Iver

Could have seen 'em before they ended: Lou Reed, Constantines

Alas, this poster will forever leave a bitter taste of what could have been in our mouth. The Beastie Boys were scheduled to headline, until Adam Yauch announced his cancer diagnosis… and now we're a little verklempt. Instead, 2009 will be remembered as the year EDM took over. Perry’s Stage took on a much larger footprint. Deadmau5, Bassnectar, Diplo appeared. And it's been bass drops ever since.

Lollapalooza 2012

6. Lollapalooza 2012

Headliners: The Black Keys, Red Hot Chili Peppers, Jack White, Black Sabbath, Justice, Avicii

Also: At the Drive In, Franz Ferdinand, Florence + The Machine, Passion Pit, The Shins, Weeknd, Sigur Ros, M83, Bloc Party, Frank Ocean, Childish Gambino, Tame Impala, Calvin Harris, Kaskade, Bassnectar, Porter Robinson

Lamest act: At the Drive In

Could have seen 'em before they blew up: The War on Drugs, First Aid Kit, Macklemore & Ryan Lewis, Aloe Blacc

Could have seen 'em before they ended: At the Drive In

Derecho! We learned a new meteorological word that stormy summer. Severe rains, green skies and lightning forced an evacuation, axing the sets of the Alabama Shakes, the Temper Trap, Neon Indian and more. A big deal was made about Black Sabbath, and Sharon Osbourne reportedly squeezed a hefty free from C3, but Geezer and the geezers played to a half-empty field. The Black Keys and Jack White are there, like, every year. Meanwhile, you could have seen a bunch of acts before they hit the big time.

Lollapalooza 2005

5. Lollapalooza 2005

Headliners: Weezer, Widespread Panic, Pixies, The Killers, Primus, Dinosaur Jr.

Also: Death Cab for Cutie, Arcade Fire, Dandy Warhols, Spoon, Tegan & Sara, Black Keys, Digable Planets, M83

Lamest acts: Perry Ferrell's Satellite Party, Billy Idol

Could have seen 'em before they blew up: M83

Could have seen 'em before they ended: Digable Planets

So. Many. Forgotten '00s bands. The Bravery! Louis XIV! Ambulance LTD! (Here's looking at your fate, Walk the Moon.) The festival was still clearly finding its feet a decade ago. Bands at the top of the poster (Primus, Dinosaur Jr.) weren’t the last to play their respective stages. Still, because of the small footprint and bill, it was quality, not quantity. When OK Go and M83 are the first acts of the day, it's a solid lineup.

Lollapalooza 2006

4. Lollapalooza 2006

Headliners: Red Hot Chili Peppers, Kanye West, Death Cab for Cutie, The Raconteurs, The Flaming Lips, Ween

Also: Wilco, Sonic Youth, The Shins, My Morning Jacket, Broken Social Scene, New Pornographers, Nickel Creek, Sleater-Kinney, Queens of the Stone Age

Lamest acts: 30 Seconds to Mars, Blues Traveler

Could have seen 'em before they blew up: 30 Seconds to Mars

Could have seen 'em before they ended: Sonic Youth

Man, Lolla was really into Death Cab in the early years. In fact, there was a good amount of bleed between Lollapalooza and Pitchfork back then. That is no longer the case. The last vestiges of emo were here, acts like Rainer Maria and the Smoking Popes. Sleater-Kinney played its third to last show… before the recent comeback. The festival expanded to three days. Kanye before he went batshit and used Auto-Tune and Sonic Youth before they were divorced? Nice. Wait, Ween was still billed above Wilco?

Lollapalooza 2007

3. Lollapalooza 2007

Headliners: Daft Punk, Muse, Pearl Jam, Ben Harper, Iggy & The Stooges, Modest Mouse

Also: Interpol, Yeah Yeah Yeahs, My Morning Jacket, Kings of Leon, The Roots, LCD Soundsystem, TV on the Radio, Spoon, Patti Smith

Lamest act: G. Love & Special Sauce

Could have seen 'em before they blew up: Lady Gaga & Lady Starlight. Well, Lady Gaga.

Could have seen 'em before they ended: Amy Winehouse, Sparklehorse, LCD Soundsystem

Everyone just assumes the Daft Punk year was the best. Though the robot duo did deliver the greatest headlining set of the modern era, there are still some clunkers here. I mean, Ben Harper as a headliner? Overall, 2007 might have been the most “indie,” with Ted Leo, Tapes N Tapes, Yo La Tengo, Peter Björn & John, etc. The festival expanded to eight stages. Cool bill, just not quite a contender.

Lollapalooza 2010

2. Lollapalooza 2010

Headliners: Green Day, Lady Gaga, Soundgarden, The Strokes, Arcade Fire, Phoenix

Also: MGMT, The Black Keys, Spoon, Cypress Hill, Chromeo, Devo, Spoon, Grizzly Bear, Mumford & Sons, Social Distortion, Hot Chip, New Pornographers, the National, Erykah Badu, Warpaint, Jimmy Cliff, Metric, the xx, Dirty Projectors

Lamest acts: X Japan, Blues Traveler

Could have seen 'em before they blew up: Mumford & Sons

Could have seen 'em before they ended: The Walkmen

What an undercard. Many of those acts just below the headliners are now headliners in their own right, others are just cool. This was the first time bands in the middle of the day—the xx, Mumford—seemed to outdraw headliners. That being said, the closing performances were fantastic. The Strokes and Phoenix ripped through tight sets on the north field. Not even Blues Traveler covering Radiohead's "Creep" could ruin it. Booking a pop act like Gaga took chutzpah, and changed the biz. Now we expect a Beyoncé or Rihanna. The fest doubled its footprint in 2010, expanding across Columbus, which offered needed breathing room (that has since been stuffed with bodies). That helped, as it was hot as balls.

Lollapalooza 2008

1. Lollapalooza 2008

Headliners: Radiohead, Rage Against the Machine, Kanye West, Raconteurs, Wilco, NIN

Also: The Black Keys, MGMT, the National, Broken Social Scene, Bloc Party, Grizzly Bear, Girl Talk, Bloc Party, Gnarls Barkley

Lamest act: DJ MomJeans

Could have seen 'em before they blew up: MGMT

Could have seen 'em before they ended: Rage Against the Machine

Girl Talk closing Citi Stage was the first time a DJ closed. Lolla never looked back. But that is not what makes 2008 the ultimate year in Lollapalooza Chicago history. Covering Rage Against the Machine felt like reporting from the fall of Saigon. Fans crashed the gates, pouring into a field overflowing with energy. Radiohead brought its beautiful light show and tunes from In Rainbows. Kanye West, touring Graduation, performed "Homecoming" in his hometown.

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