How Chappell Roan Broke an Attendance Record at Lollapalooza Chicago

When Chappell Roan released her debut album, The Rise and Fall of a Midwest Princess, last September, it didn’t immediately crack the Billboard 200. In fact, it took more than six months for the album to debut at No. 127 on the chart dated April 6 — following a boost in exposure after Roan opened on tour for Olivia Rodrigo. 

Now, nearly one year later, both Roan’s album and her stardom continue to hit new highs. On the Billboard 200, Midwest Princess has entered the tally’s top five, hitting a new peak of No. 4 after 19 weeks on the chart. Over on the Billboard Hot 100, the pop star currently has six songs scattered across the chart, with her latest single, Good Luck, Babe!” climbing the highest. The hit, which this week entered the top 10 at No. 8, has become Roan’s highest-charting entry to date. 

Roan’s chart dominance has been a long time coming, and a moment her longtime manager Nick Bobetsky (State of the Art) has been patiently waiting for. Bobetsky met Roan in 2018, after her previous record label, Atlantic (from which she was dropped), shared some of her unreleased music. “Her immense talent was clear immediately,” he recalls. “She’s always been a true artist.”

Since then, Bobetsky and the team have “focused solely on building the Chappell Roan universe and trusting that the greatness of her and her music would thrive” — just as they are now. And on the heels of a record-breaking Lollapalooza Chicago set, which saw the festival score its biggest-ever daytime crowd, Bobetsky has earned the title of Billboard’s Executive of the Week. 

Here, Bobetsky talks about the success of “Babe!”, Roan’s festival takeover this summer and more. As he says, “I take great pride in helping shape [an artist’s] runway to success, however long it needs to be.”

“Good Luck, Babe” has become the highest-charting song of Chappell’s career, entering the Hot 100’s top 10. What key decisions did you make to help make that happen?

When Chappell finishes a song she’s excited about, we’ve learned to follow her instincts and hit go; in this case, putting a strategy together with Island to get the song out quickly. Chappell has always been about building, which in turn brings momentum. People became fans on their own schedule over the course of months, having their own moments of discovery. “Good Luck, Babe!” was the first time since her sold-out tours, her album release, the snowball effect she was experiencing, where the broader fanbase could share a fresh moment together. That shared and focused excitement, paired with the incredible song, gave us a strong launch. We’ve been able to not only grow the song since then but the entire album because we’ve continued to stay focused on the same core things — building, and consistent momentum. 

Chappell has a total of six songs on the Hot 100 right now. How are you supporting so many songs at once and determining which one to push next?

Chappell’s songs speak for themselves, her performances are second to none, and her universe has never been about one song, one moment, or one driver — and the fact that we have so many songs in the Hot 100 is a testament to that. We aren’t cramming anything down anyone’s throat, and fans are listening to multiple songs at once. In terms of pushing the next song, we are in the incredible position to have a lot to choose from. That said, I don’t actually think it’s about choosing to push one in particular, it’s about paying attention to which one is thriving the most. We have live audience reactions, fans online, streaming numbers to lead us. What excites me the most is the nonlinear nature of it all — that her next song to push is likely to have been out for nearly a year. 

Dan Nigro signed Chappell to his Amusement label before she signed with Island. How did you help guide her transition to the major label?

Dan started making music with Chappell during her previous record deal, and he remained committed when she and the label parted ways. We released a series of singles independently and built a very loyal and loud fanbase. We focused solely on building the Chappell Roan universe and trusting that the greatness of her and her music would thrive. It started to get loud, labels started circling, and Dan’s Amusement label was a continuation of their creative collaboration, now in partnership with Island Records where she landed in the end.

Her debut album, The Rise and Fall of a Midwest Princess, was released in Sept. 2023 and just this week — almost a year later — hit a No. 4 peak on the Billboard 200. What are you and the team doing to help sustain its renewed momentum — or planning to do still?

Everything in the world of Chappell Roan is about building, staying true to her vision, and embracing the 100% rule — that if the answer is not a true 100% yes, it’s a no. Chappell’s growth is a very special pairing of consistent commitment to momentum, paired with ensuring that every moment is executed to the fullest degree. We’re in an era of tons of noise, the fear of fleeting moments, pressure to say yes at every turn, and our approach is different. She says yes when it’s right for her universe, and people want to keep joining in. The momentum is sustaining itself because it’s real and reflective of incredible music and artistry having real cultural impact.

Chappell’s Lollapalooza Chicago set saw the largest day crowd in the festival’s history across its global franchise. What were you anticipating and how did you help her mentally prepare?

Every festival this summer Chappell has played has been bigger than the previous. We knew this was going to be big, no one knew we’d break records. We work really hard to surround her with visionary creatives, a rock solid touring team and ensuring every element is top-notch. I’m not sure how you can mentally prepare for a moment that big, but she’s born for moments like this.

What kind of boost has she gained from that news-making set?

We’ve seen new daily peaks in consumption and online conversations, but I feel the biggest boost because it feels like mainstream media, fans and the industry alike all saw it coming and were ready to celebrate. It really feels like a, “See, I told you so,” moment — not from us saying it, but from the masses screaming it. 

What’s the key to managing a pop star today?

Respect, partnership and belief in the artist. Sure, the strategy, relationships, business decisions and all of that are important, but that’s actually the easier part. When you have a generational pop star, the real key is the shared vision and commitment to their greatness long-term. I take great pride in helping shape their runway to success, however long it needs to be.

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