Booking/Artist Development: Where Are Tomorrow’s Headliners Coming From? (Pollstar Live! Panel Recap)

What makes a headliner? Has the definition changed? And where do you find them? These were some of the questions discussed during Pollstar Live! 2025, on a panel led by Jonathan Azu (founder & CEO, Culture Collective), Robbie Brown (UTA), Kiely Mosiman (Wasserman Music), Milly Olykan (senior vice president of artist development & global touring, Live Nation), Jacqueline Reynolds-Drumm (CAA), and Del Williams (Danny Wimmer Presents).

Azu opened the session by asking the question, “How do you define a headliner?”

To which Williams responded, that the definition hadn’t really changed. Headliners are going to drive ticket sales, and generate passion. And they’re “the act you curate the day around.” He said the main factor was having the right network or data insights in place, to find out the real numbers artists were able to pull.

Azu wanted to know if there wasn’t also such a thing as hype around an artist that had to be factored in irrespective of their sales potential.

Reynolds-Drumm confirmed this: “Intentionality is key,” she said, knowing the right time to headline, making sure it’s the right stage, stage, time, etc. “Cultural cachet plays an important role,” she said.

Mosiman explained, that when you were headlining a festival, you want to create that cultural moment that goes beyond the event. Production level and feeling need to be bigger than the show.

Brown added, broadcasting the show has become part of that mix. “People are looking at how to touch every part of the globe at one time,” he said, adding that timing and strategy was “everything. Don’t waste your shot. Sometimes ‘no’ is the right answer.”

Reynolds-Drumm agreed: “don’t skip steps,” she said, explaining that when and where to headline should be part of an overall vision that may take 12, 18, 24 months or longer to execute in full. She said it was good to know what the artist’s goals were, in order to make the right decisions. “Make choices on growth and data, and not ego,” she said.

Williams agreed, that “there’s no substitute for navigation and critical thinking. It also depends what you want as an artist” – ie longevity and a potentially global career or a short-term squeezing of any given market. He said he saw “artists moving up the ranks too fast all the time. If that happens, where do they go from there,” he said, adding that it was okay to sell out a venue that was 1,000 tickets smaller than what could have been sold.

Mosiman said, it was hard to break an artists, let alone make them a headliner, but if the whole team involved red “from the same script,” it definitely made things easier.

Olykan who’s played a big part in the rise of country outside its home market USA, couldn’t agree more. She said there were many new managers in country music with unrealistic expectations for their artists. Sitting down with artist, manager, agent, taking time to properly plan, be part of the strategy/team.

She named Lainey Wilson as a poster child for how to build a career globally at the same time. “She hasn’t missed any of the steps,” she said, pointing out that Wilson first visited the UK in 2018. “It should take time to build a headliner,” Olykan said.

“Moments are easy, a career is difficult,” Azu summed it up.

And Mosiman added, that since you never knew who would be the next headliner, to treat all your artists like they could.

When the panelists were asked about great current examples of artists that were on the verge of becoming headliners, Williams picked Spencer Charnas from Ice Nine Kills, calling him a marketing and bradning genius, “making all the right decisions, and tapping into what his fans care about on all the relevant channels.”

Olykan said the two names constantly being mentioned in country were Megan Moroney and Zach Top. Reynolds-Drumm picked Gracie Abrams, and Mosiman Role Model. “The way he runs his TikTok is [a masterclass],” she said.

All of the above mentioned upcoming artists are currently playing the circuit, moving up the capacities, with no end in sight.

One potential pitfall, said Olykan, was wanting to headline too early. Another challenge was to convince artists from the U.S. to come to Europe, and especially to spend some proper time in the market touring and doing media. It was the only way to build their story.

“Some artists don’t like building international, if it means going into smaller rooms, so egos also play a role,” she explained.

Mosiman warned not to overdo it, and to remember that you were dealing with humans, who needed time off every now and again. Or, in the words of Reynolds-Drumm, “tour smarter not harder.”

One of the big myths that sometimes prevailed but simply wasn’t true anymore, said Brown, was that you still needed a radio hit to be an eligible headliner. “You don’t,” he said.

Williams agreed, a radio hit “used to be the be-all and end-all, but that’s changed. You have many headliners, who haven’t had a real hit.” But then again, he added, the definition on what constituted a hit has also changed.

And he still saw plenty of room for the legacy headliners, many of whom were also thriving in the current nostalgia boom. “They have the songs, the catalogue,” he said, “we need those.”

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