Who Are Lollapalooza's Best-Ever Headliners?

So it’s Lollapalooza weekend, although it’s not like anyone is going to be gathering in Chicago’s Grant Park like hundreds upon thousands of music fans have been doing every summer since 2005.

I attended Lollapalooza 1992, 1994, 1995, still regret not seeing the Ramones in 1996, and travelled to Chicago in 2009 for the legendary Lou Reed among many, many others.


Before that - specifically 1991 to 1997, with a one-off revival in 2003 - Lolla was of course a travelling festival, and the most fun an alt-loving young adult could have in a single day! Ever the innovator, Perry Farrell’s brainchild isn’t going to let COVID-19 completely ruin a celebration of what makes live performances magical.

Starting July 30th at 5 PM Central Time and running until August 2nd, Lollapalooza will broadcast a semblance of a 2020 edition virtually via YouTube with what looks to be a mix of archived sets and pre-taped appearances by artists who would’ve/should’ve been part of this year’s lineup. Oh, and Michelle Obama too?

While these are some mighty impressive names, it is really only a drop in the bucket of the Lake Michigan’s worth of talent that has made Lollapalooza one of North America’s most enduring music and cultural happenings. Not to mention culinary! Besides making this old-timer long for the days when I used to stand in a field for hours on end, it’s motivating me to want to comb through history and do a definitive ranking of Lolla headliners. So here’s the deal - Using Wikipedia or whatever means necessary such as your own memory, comment on this thread as to who you think has been Lollapalooza’s greatest bill-toppers.

I’ll get things going; there are some easy choices like Jane’s Addiction and Rage Against the Machine. Pop isn’t my usual cup of tea, but in 2010 Lady Gaga proved she had arrived as a proverbial main eventer, could more than hang with the boys so to speak, and wasn’t afraid to do a little crowd surfing to boot. I’ll give you the weekend to let me know who your picks are. (The Weeknd is eligible in case anyone’s wondering, having headlined in both 2015 and 2018!)