Lollapalooza, The Best of the Fests
2010, 2015, 2025...Lollapalooza has always left me in love
HELLOOOO CHICAGOOO (or wherever you are). It’s the weekend, this is Down the Pipes, I’m James, and this week I’m filing from the former W Lakeshore, now “reflagged” by the Bonvoy Gods as The Wade. If you like deep dish, having your corporate card declined at Alinea, Ozzie tributes that are blurrier than his last 10 years, midwest romance , the greatest music festival in America, and the annual digging up alcohol in Grant Park the first weekend of August, I’ve got you. If you don’t like those things, reevaluate your priorities.
I love Chicago. I’ve always loved Chicago. Did you know they’re called the Windy City not just because of the lake effect winds, but because they know their politicians have always famously been full of shit? Or that their other nickname, The Second City, was an insult that they turned into a tagline? Like they were just like: “Yeah okay, you got us.” It’s so charmingly Midwest.
Home Alone, Family Matters, and a whole slew of Brat Pack films painted Chicago like a suburban dreamscape, and friends I know who grew up in the area describe it as not far from the truth. Other friends, who grew up in very different parts of Chicago, describe it as “not great” and “totally unsafe.” Both vantages can be considered honest appraisals; like most 20th century American cities, the red lines are clearly drawn and labeled on the maps there.
Gonna keep it light on the pipes this week though, no more talk of red lines. I’ve got some muck on Cuomo I’m working on raking and I’m tracking a whole universe of internet drama to dish on in due time, but this week I’m just self indulging memory lane. It’s August, walk with me.
Lollapalooza was launched as a farewell tour for Jane’s Addiction in the early 90’s. I was quite literally still wearing a diaper in 1991 (not because I wasn’t toilet trained at 4 but because I ate a penny that summer and had to go back to diapers for a few weeks, sorry mah), so I’m going to skip trying to unpack the early touring years of Lolla. I hear they were a blast if you were of a certain alternative ilk in the 90’s, there’s a documentary on Hulu about it. I was still eating pennies so ¯\_(ツ)_/¯
But I first showed up at Lollapalooza when it was settled in Grant Park in 200…9? 10? 8? This was a blurry time in my life, I had just become Gawker’s sales guy in Chicago, so I was flying out there once or twice a month to pitch all day and then eat insane dinners with media buyers at night.
I ate at Moto like a half dozen times, a kind of Alinea Lite that made molecular gastronomy less silver spoon, more accessible. RIP Chef Cantu. The Publican, my second favorite Chicago restaurant for client debauchery, still allows you to order a six pack for the kitchen off the menu. Once during a client meal at Alinea, the brand new Gawker Amex declined and I had to put it on my personal “for emergencies” credit card because I did not have $3,000 in my checking account at 23 years old.
They have a whole discreet way of pulling you aside when your credit card declines at Alinea, by the way…they made it seem like they had a surprise for me in the kitchen, and then shooed me into manager’s station to show me the decline code. Definitely part of the experience in my book. And they were kind of jerks about it at L20, if I recall. Much more, “Sir, this card is DECLINED.” That card was often convinced it was actively being stolen.
As it goes, Chicago is, was, and continues to be a drinking town, so these memories are getting pieced together with whatever archives I still have. It looks like my first year was 2010, thank you Jay and Nell for not getting sober until after this photo was taken:
This first year, if memory serves, I was staying at The Allerton Hotel on Michigan Ave, a bit of a hike from the festival but walkable if you were 23 and cranked up like I was. Keller (bonus points for you if you know who I’m talking about) slept on my couch that year (his first too, I think) and took me to a great burger joint called Kuma’s Corner, still a legendary pre-Lolla tradition I think he keeps all these years later.
The next few years of Lollapalooza, I have very little physical evidence of. All I have from 2011 is this sorely incomplete Spotify playlist I made:
This year was also the year Radioshack sponsored Gizmodo’s Lollapalooza coverage (before their CMO fled to Australia for sponsoring Lance Armstrong all those years). That marketing team was low key incredible to work with though, they gave us a bunch of camera equipment and let us send a Gizmodo reader to “cover” the festival. I’m sure we did more than this, but it’s also possible that this is all we did. Coldplay played and I remember not being particularly impressed, same deal with Eminem. Foo Fighters, however, had a moment with a downpour that to this day is one of my top 10 all time live music moments:
My favorite find that year was Foster the People, who played a sunshine set on one of the smaller stages. Pumped Up Kicks was just breaking, and they got roped into playing a 1am set at the Hard Rock Hotel (closing for Phantogram), long the gold standard of Lollapalooza afters.
2012…again, not a lot of evidence remains. I remember Miike Snow being big and not really caring…I was there to see Franz Ferdinand and Black Sabbath. Ozzy sounded phenomenal despite looking old, even then. Not that you can tell with 2012 smartphone technology, I think this was taken with a Blackberry:
I think Passion Pit was a headliner this year? Is that possible? Florence & The Machine crushed. 2012 was a weird year in Chicago, this was the year a derecho blew in and I had to shelter in the artist gifting lounge at the Hard Rock. Acts I should have seen but didn’t: Jack White, Justice, Childish Gambino, Frank Ocean. But this was the crowd for Miike Snow:
2013 was the year I fell in love with a girl at the Perry’s stage, it was the sloppy “who are you? Oh, we have friends in common? Let’s make out” interaction that was once terribly common for 26 year olds at these kinds of things. This was also the year I snuck a small A-Team of clients into the Hard Rock afterparty through a stairwell and back of house area. We were apparently very close to the stage:
This was also the year that Zedd’s Clarity broke, a song with particular significance to my universe because Matt wrote it during the Matthew Koma EDM era. That was one of the first time tens of thousands of kids were bopping along and making out with strangers in a field to one of his tunes, it was pretty incredible to witness and participate in first hand. That whole weekend of magic made me seriously consider calling Chicago home for a period of about 8 months.
(Note: Don’t do this. Lollapalooza happens to be during the nicest weekend of the nicest month in Chicago, falling in love here during the summer is too easy and will be brutally tested during numerous delays at O’Hare in February)
2014 was the year I don’t think I spent much time at the festival itself…the SoHo House had just opened in Chicago so they were having sick after parties that it was easier to sneak into if you got there early, couldn’t tell you who was DJing but it was probably a Ronson or two. Cash Cash—managed by my then-roommate and forever homie Jason—were successfully making the jump from Warped Tour to EDM, I vaguely remember it being 4am at this club and the fluorescent lights coming on:
Can any of my Chicagoheads name this club? Is it Berlin? Or Sound Bar?
2015 was my last summer in Chicago for nearly a decade. Dave (of Croatia vacation and Key Club fame) was convinced to celebrate his bachelor party in Chicago the first weekend in August, so I got to share my love of Lolla with him and a handful of buds I had known since college or earlier.
Besides an Uber accident en route to The Publican and Joe drunkenly taking himself to a Morton’s dinner, the rest of the weekend was pretty legendary. Per official bachelor party rules I will not disclose our full itinerary, but we did make it once again to the Hard Rock after party (now being hosted, weirdly, at the Renaissance across the street). Wet was playing, if you don’t know them you should.
My Lolladays ended when I moved to Vegas in late 2015 and started spending every weekday in a festival environment, but that’s a different story for a different newsletter. The idea of traveling to see pop music was no longer appealing…this is about when my Burning Man and Phish arcs started. Again, a different set of stories. But whole lives have been lived and died between the last time I went to Lollapalooza and today, is my point.
Until this year. I was back. Winnetka Bowling League was playing on the Lakeshore stage and doing a House of Blues after party, and I just couldn’t miss my best friend playing on a stage that I melted in front of so many times before.
I’ve been backstage at Lolla before, no clue why or for what but being back there again felt familiar. Seeing the festival from that vantage, 10 years later, now from the view of the folks putting on the festival and not consuming it…it had me emotional.
The number of friendly faces back there reminded me just how many years I’ve spent adjacent to the music industry…there were old colleagues and brothers like Pedram and Keller, different world friends like Oakley and Molly, other sound guys and techs I’ve crossed paths with over the years, former ad assistants who are now ad executives…this past weekend in Chicago was a merging of like six different cinematic universes of mine.
Foster the People, a band I had seen on a small stage 15ish years ago, is now playing just before the headliner on the main stage. Pumped Up Kicks was already a song I associated with this festival, but this year, seeing 30,000 kids (many of whom were literal babies when the song came out) singing along to a song I used to rage to was a real full circle moment. I am grayer, Mark Foster is too, but the kids don’t seem to mind.
Matt will likely be on that main stage at some point in the next 15 years too, probably sooner. Oakley was already up there for Cage the Elephant. So was Jason with Halsey (who played the tiny BMI stage in 2015 before headlining the following year). Keller is seemingly always up there whether or not it’s his artist, they all know him and are happy to have him side stage. It’s a special thing to be anywhere near that kind of musical trajectory, it puts you in rarefied strata to be able to command that size of a crowd.
I’ve been to lots of festivals. None of them are so centrally located, well booked, well fed, well appointed, well organized, and well maintained as Lollapalooza has consistently been over these 15 years. The people who go are the best kinds of music fans, they show up early and they stay out late. They buy food and alcohol, they have a good time but generally know how to handle their shit.
Lolla is still a starter festival with none of the camping tribulations of Bonnaroo, the celebrity pressure of Coachella, or the maze of VIP afters at Ultra or EDC. But the city attracts the most enterprising Americans who don’t feel any affinity to a coast or Texas, and they proudly do wild shit like this every year:
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I spoke with the security guard who was guarding the entrance to the backstage area, and he told me it was his 15th year doing security at the festival, his first year was the same as mine. He worked his way up to working that VIP gate, leading me to believe that all of the staff across the entire festival—from the cart drivers to the caterers—are long time pros too. They keep coming back year after year because there is no better job for a week in August in Chicago, and as long as they keep coming back, I’ll be coming back too.
This year was beyond expectation though, I had braced for disappointment. It can be crushing to return to old stomping grounds to see a bunch of butt muncher 23 year olds awkwardly texting each other from across a field between sets and songs. That was a bit crushing.
More importantly on the crushing front, Matt and the band crushed their numerous sets across town, the crowds were stacked at each show and singing along. During a more mellow “Toyota Music Den” set there were fans requesting songs that I don’t remember and Matt doesn’t know anymore, really made me appreciate for a moment what the algorithms can do for surfacing deep cuts and/or songs that are strong enough to earn an audience over time.
We got to spend the weekend with a world class jump roper and stunt dude named Porter who flip flopped like Benson Boone all over the city, shout out to that dude. He’s got a crazy life, you can pretty much hire him to do anything dangerous, he’s never done car stuff but said he’d love to “figure it out” so if anyone would like to pay us to pay him to drive recklessly let’s chat.
Anyway, it’s late on Saturday and I’ve got company coming tomorrow, so let’s wrap this up with some Lolla 2025 highlights.
Acts this year I’m glad I saw: Mk.Gee (good but not as good as
promised), Doechii (I get it now makes total sense), Still Woozy, Sabrina Carpenter (was on her team until Olivia brought out Weezer, still good show), oh and seeing Djo do this was pretty much all of my feels from the weekend politely boiled down to a :23 second TikTok.Charlotte Lawrence was great and if you were hip you saw her at Bowery this week, and Caroline Kingsbury will blow minds next summer with OUR HOUSE. Del Water Gap (no relation) also gets Down the Pipes approval, he’s a friend of the
/Boy Problems universe via DWG’s guitarist Nick. Sammy Virji and 2FRIENDS were the only DJ acts I saw, I will say the DJs rediscovering disco drops is a promising development for dance music in general.Plus, completely unrelated to all of the above, Kidder and Strle gave me a tour of the soon to be renovated Onion office. I got to paw through a binder called The 9/11 Binder and by god, knowing that binder simply exists is worth your subscription.
Chicago, never change.
Until next time!
I lived in Chicago from 2011 to 2015. I loved it and I miss it!!! The best city to live in as a young-mid20s professional.
I love reading about your life. It’s my favorite part of the “newspaper” I subscribe to.