Simon Kessler’s Lollapalooza playlist

Of the many experiences bound to summer, the pinnacle, arguably, is the music festival. In their barest sense, they are a kind of raucous, gorgeous communion, soundtracked by recording artists, famous and otherwise undiscovered. And perhaps, most importantly, they’re underpinned by proximity, by shoulder-to-shoulder intimacies; drinks, tents and bodies, shared. The COVID-19 pandemic has robbed us of a great deal, and made such large gatherings not just logistically difficult, but morally objectionable. This for all intentions, was the year that we, like those infamous Somerset fields and Gräfenhainichen’s industrial playground, lie fallow without choice. 

But even if we cannot yet share space and dance like we once did, there are some who would not let us forget the magic of the festival so easily. Simon Kessler is one such man. 

Kessler is a talent buyer/book for C3 Presents, the industry force behind dozens of acclaimed festivals, perhaps most notably the infamous Lollapalooza. The original Chicago festival is the longest running of its kind in America, playing host to hundreds of thousands of revellers each year, and has spawned successful iterations in Paris, Germany, Brazil and further afield. But to paraphrase an age-old maxim: where there’s a will, there’s a festival. This year, owing to summer’s cancellation at the hands of the pandemic, Lollapalooza, for the first time in its near 30-year history, went digital. 

‘When we “cancelled” it, we actually announced that we were going to do Lollapalooza 2020 still, but in a virtual capacity,’ says Kessler. ‘It’s been an interesting learning experience. We hadn’t really done too much in that virtual festival space.’

For his team, it was about moving beyond the living room-based live performances that have become commonplace over the quarantine period. For this iteration, locations ranged from panoramic views of LA to sewage tunnels. 

The programme blended exciting content from artists created during quarantine, as well as the festival’s own extensive archival footage (including Paul McCartney and OutKast), to create a truly special digital event. ‘[We] had Vic Mensa performing with The Bucket Boys in Chicago in all these cool locations, and then he goes into the Skydeck, which is 110 stories above the ground. At the end of the day, it came out to be a really cool streaming event, and it made us just miss live shows even more.’

Kessler’s job requires a phenomenal amount of research, along with a degree of musical clairvoyance. ‘We book [acts] in a year out, [so we’re] really kind of looking forward and estimating. And also trying to figure out what’s going to be the best come next year, not what’s the most popping thing right now. They don’t always have to be selling out 5,000 tickets right away. Sometimes, we’re just looking for the band that’s selling out all of their show’s 150 tickets and has a record coming the next year.’

While the digital space, as forensically curated as it might be, will perhaps never truly substitute for the heat of the throng crushed up against you, Kessler sees continued room for them even as we return from our global hiatus. ‘Maybe more in the way of supplementing live shows versus replacing them,’ he says. ‘I think the digital transformation, moving more and more towards digital [experiences] is inevitable, both as an amazing tool for breaking artists and allowing artists to play from their hometown to a global audience.’ 

On his playlist

‘Booking a festival is like creating a delicate recipe – you want to balance out the ingredients perfectly to create a beautiful final product,’ says Kessler. ‘Our goal is to select the right mix of bands to fit into the overall schedule puzzle: some new and some old bands that are continuing to grow; bands that are pushing boundaries and so on. This playlist is a sample of the many different kinds of artists that we book.

‘I’m starting this playlist with “Redbone” by Childish Gambino. We had Gambino headline Lolla Chicago in 2019 and it was a truly incredible performance. It also includes The Strokes, who played Lolla Argentina in 2017, J Balvin, who was the first Latinx headliner we had in Chicago, and Chance the Rapper – he first played the festival in 2013 on the smallest stage on an early slot. Four years later, he returned again to be the number-one headliner of the festival, to play to maybe the largest crowd ever for that slot. It’s amazing to work with bands through the various stages of their careers and to see them grow into stars.’