Who is the best Lollapalooza headliner of all time?

A fixture across multiple Lollapalooza eras, Trent Reznor's industrial rock project delivered legendary mud-soaked sets that became defining moments of 1990s festival culture.

Headlined in 1996 in a controversial booking that proved the festival's genre range, delivering a thunderous metal headlining set that expanded Lollapalooza's audience dramatically.

Headlined in 2007 at the revived Chicago-era festival, delivering an epic grunge-era set that reminded a new generation why Pearl Jam are one of the greatest live bands of all time.

Co-headlined in 2007 with their electrifying pyramid stage show, one of Lollapalooza's most visually spectacular performances and a landmark moment in electronic music at major festivals.

Headlined in 2008 and 2016, widely regarded as two of the festival's greatest-ever sets, with Thom Yorke and band delivering hypnotic, career-spanning performances.

Headlined in 2006, 2008, and 2009, making him one of the most frequent Lollapalooza headliners with increasingly elaborate, theatrical performances that redefined hip-hop at festivals.

Headlined in 2010, bringing explosive pop spectacle and theatricality to Grant Park in a performance that cemented her status as one of the most compelling live performers of her era.

Headlined in 2011, delivering a rain-soaked performance widely called one of the greatest in festival history after a storm-delayed set saw Dave Grohl and band play deep into the night.

Headlined in 2014, delivering a career-spanning hip-hop set that reaffirmed his place as one of rap's greatest performers with unprecedented energy for a festival main stage.

Headlined Lollapalooza 2015 with the Beatles legend delivering a multi-hour show-stopping set packed with classics that had 100,000 fans singing along to every word.

Headlined in 2017 as a Chicago native returning to his home city's biggest stage, delivering an emotionally charged set celebrating his rise from local hero to global superstar.

Headlined in 2019, becoming one of the biggest pop stars to close out the festival's main stage with a meticulously produced set featuring elaborate choreography and powerhouse vocals.

Headlined in 2023 as one of hip-hop's most critically acclaimed artists, delivering a Pulitzer Prize winner's vision of American culture in what many called the greatest Lollapalooza performance in years.