When Shaboozey inked a deal six months ago to perform at this year’s Outside Lands Festival in San Francisco (August 9-11), festival organizers could never have imagined that by the time the festival came around, the Virginia-born country singer would have the No. 1 song in the nation on the Billboard Hot 100 chart. Heck, “A Bar Song (Tipsy)” was nearly two months away from being released when the Outside Lands Festival Lineup dropped in late April, and Shaboozey’s name appeared on the bottom third of the lineup poster.
For Another Planet Entertainment (APE) President of Concerts and Festivals Allen Scott, it was more about booking up-and-coming country music talent to surround a lineup that features Sturgill Simpson and Post Malone’s country sets among its headlining acts. Charley Crockett and Paul Cauthen are also on the weekend bill, but Shaboozey presented a bit of a chance, one that really paid off for APE in yielding a powerhouse crop of country stars.
“Sometimes it’s better to be lucky than good,” Scott says with a laugh on a call from APE offices in Berkeley. “When we booked Shaboozey, he had never really toured yet. We’re close with Empire in San Francisco [his label] and they had talked to us about a number of their artists but he really jumped out at us. We hadn’t even heard of this song, but we liked the whole vibe. And the further down the lineup poster you go, you can take more chances. Every once in a while you have something like Shaboozey.”
A lineup this top-heavy on country music is an anomaly for the 16-year-old festival, widely-regarded as one of the biggest and best in the country. If Coachella is 1A in California, then Outside Lands is easily 1B, a similarly-sized tone-setter for the festival industry. Going this all-in on country says something about the current music industry landscape.
Besides “A Bar Song (Tipsy)” atop the Hot 100 chart, Post Malone and Morgan Wallen’s pop country duet, “I Had Some Help,” sits at No. 2 on the chart dated July 27, after its own run at the top for a period. To have the artists behind the top two songs in the nation at your festival is a fortunate position to be in, yet Scott says the real challenge is in striking a balance between capitalizing on “unique opportunities that aren’t the same as other festivals,” while still capturing chart success.
Enter Sturgill Simpson, who hasn’t played a live show in nearly three years and will be closing out Outside Lands on the main stage. The performance (along with a festival night show underplay at the APE-operated The Independent; also in SF) comes a month before he embarks on a tour in support of his latest album, Passage Du Desir. Simpson has been enigmatic to say the least, spending most of this dark period based in France, only to emerge with a new alter ego, Johnny Blue Skies. It’s par for the course for arguably the one true psychedelic outlaw country act — and definitely the only one to win a Grammy.
“That’ll be the first time I’ve stepped on stage in years,” Simpson told GQ. “And I’m headlining closing night. It’s perfect. I’m Tyson with the towel, man, I like the pressure, I’m like the underdog. I’m gonna go punch everybody in the teeth. I’m pumped, bro. I’m jacked.”
A unique experience? Check. One can’t help but think APE has exercised a degree of foresight with Simpson as well. Because while he experienced success early in his career, it wasn’t on a mainstream scale. Now with country topping the charts, he seems poised for an even bigger breakout than before.
Outside Lands has made a habit of banking on these breakouts. In 2022, it was the first major US festival of its size to book SZA as a headliner, well before SOS came out. Even Lizzo’s 2021 headlining set might’ve felt a bit premature, but definitely proved to be a worthy choice. And while Post Malone has been an established name in hip-hop, he was tabbed to play a country set at this year’s Outside Lands well before he ever announced his country-focused F-1 Trillion Tour. He was booked even months before his transcendent Stagecoach Festival performance effectively set this current career arc in motion.
Yet while Coachella has a property in Stagecoach that it has historically funneled all of its country-leaning acts to, Outside Lands is taking a leap in doing it at a major summer festival that caters to fans of all musical styles. Whether fans will respond to it and whether other festivals will follow suit remains to be seen. But Scott has witnessed this changing of the tide before and is ready to confidently navigate these waters.
“It’s like when Glastonbury put Jay-Z on headlining for the first time [2008] and there were people scratching their heads saying things like, ‘Why do we have a hip-hop artist when this has been a rock festival and blah blah blah?’” Scott says. “So you have those naysayers who ask ‘Why? We didn’t ask for this!’ But look, we’re thinking about what people are asking for or want, but we’re also trying to lead people, too.”