This year, Lollapalooza celebrates its 25th anniversary as a music festival. It’s had some ups and downs, including a couple of years when it went away entirely, but since settling down in Chicago back in 2005 things have been smooth sailing. Things have expanded exponentially in the last decade alone, with more stages, more artists and now more days than ever before. Yes, for the first time ever (and in celebration of this milestone), we’ll have four full days of music and mayhem. If three days and 130 artists somehow wasn’t enough to make your head spin, four days and 170 artists practically crosses the line between enjoyment and punishment. I’ve nearly killed myself in the past attempting to cover every single day of this festival for the last 11 years, and in all honesty I’m quite concerned with how I’m going to survive year 12. Don’t overextend yourself, drink lots of water, and wear comfortable shoes are just a few pieces of advice I can offer and will be abiding by myself.
That said, with four days of music it gives you an even greater opportunity to enjoy some of your favorite bands and discover some great new ones. Instead of analyzing every artist on the lineup, or even taking an hour-by-hour look at the insane schedule, let’s try something a little more sensible and manageable for 2016. In honor of 25 years of Lollapalooza, I’m going to recommend 25 can’t-miss artists who will be performing at the festival this weekend. They’re broken down by day, and distributed evenly across the weekend with the exception of Sunday, which has one extra artist just to hit that magic number. The only downside in limiting this to recommending six (or seven) artists per day is that a few really cool acts inevitably get left out. If you’re going all four days it’ll be tough to catch everything worthwhile as it is. The way these picks are structured, there’s not a lot of time slot conflicts happening, so you could theoretically see just about all of these artists if you play your cards right.
Join me after the jump for the full list of 25, complete with multiple audio/video streams from each. Best of luck to you if you’ll be in Grant Park this weekend. I’ll see you on the battlefield. Follow my Twitter and Instagram feeds for live, on-the-ground reports all four days.