Sturgill Simpson Parlays Absence Into Megafest Headliner Status

photo: Semi Song

When the history books are written about this era in country music, Sturgill Simpson will play an integral role. It’s not that his songs or albums constituted a commercial blockbuster. No singles made it onto radio, let alone in the Top 10. The Gold status for his magum opus Metamodern Sounds in Country Music is admirable, but nothing major compared to the Platinum, Double Platinum, and Triple Platinum legacy of some of his contemporaries and predecessors like Cody Jinks and Tyler Childers.

It was the influence that Sturgill Simpson had on the music that was the difference maker, namely that he opened the doors for folks like Chris Stapleton, Tyler Childers, and Zach Bryan. This is what makes his legacy so important. You can draw a direct line from Sturgill Simpson to the resurgence of quality songs and a more country sound permeating country music today.

Right before the pandemic, Sturgill Simpson and his protégé Tyler Childers were booked on a first-of-its-kind arena tour for 2020. At the time, it was unprecedented that two performers not found on country radio could pull off such a feat. And the fact that many of the dates sold out, and some on multiple nights proved the economic viability of the music.

Unfortunately though, the tour was cut short abruptly due to the pandemic, with all but a few early dates left unfulfilled. Tyler Childers opened the shows, and Sturgill Simpson closed them out as he should have since Sturgill clearly was the senior performer. But at that time, Tyler was perhaps even a larger draw than Sturgill due to the explosion of interest in Tyler’s album Purgatory. It probably wouldn’t have been possible for Sturgill to fill arenas himself, and his album Sound & Fury was polarizing to some country fans.

Then in 2021 when Sturgill Simpson re-appeared performing on Willie Nelson’s Outlaw Festival, he ruptured his vocal cords. This basically facilitated Sturgill’s retirement from touring. And along with fulfilling his five album career pledge with 2021’s The Ballad of Dood & Juanita, Sturgill Simpson basically retired from music in total.

Since then, Sturgill Simpson has been mostly a recluse, appearing in some acting projects, but probably not enough to consider him a full-time actor. He’s also taken some gigs as an album producer. But again, they’ve been more here and there than a full-time gig. At one point Simpson talked about going to college, and has always always said he wants to spend more time with his family. Only one Gold album or not, Simpson surely makes enough mailbox money to not need to tour incessantly.

But you have to tip your hat to Sturgill on how he’s leveraged his absence into top tier headliner status here in 2024. As the old saying goes, absence makes the heart grow fonder. We saw that with the Turnpike Troubadours, who took their indefinite hiatus and parlayed it into headliner status. Now Sturgill Simpson has done something similar.

In late April, Sturgill Simpson announced his first show in three years, and it was as a headliner of the Outside Lands festival in San Francisco, CA, August 9-11. He also revealed that he’d be reuniting the most legendary lineup of his band to play it, including guitarist Laur Joamets, Kevin Black on bass, and Miles Miller on drums.

Then this week as Austin City Limits Fest announced its 2024 lineup for October 4-6 and 11-13, once again Sturgill Simpson’s name populated the largest font right beside bands like Chris Stapleton and Blink-182.

For some Sturgill Simpson fans, soldiering through a multi-genre megafest like ACL, or a more indie rock-oriented fest like Outside Lands is a juice that’s not worth the squeeze. They’d rather see Sturgill Simpson go on a theater/amphitheater tour this summer. But the fact that he likely won’t is the reason he’s able to be booked as a headliner for these shows, and probably earn a pretty penny doing it. It’s kind of genius, as he’s let his legacy achieve a sort of mythological status.

Live music right now is in the make, and festivals are popping up all over the United States to take advantage of it. Unfortunately though, this has also created more competition than we’ve seen in years, including for independent country megafests that in 2022 and 2023 sold out immediately, and in 2024 are struggling to fill capacity since patrons have so many more options.

This has also resulted in a drain for headliner-level talent. Since so many acts can go on their own arena and stadium tours like we’re seeing from Tyler Childers and Zach Bryan, they don’t need to take the festival headliner gig. So the demand for headliners has never been greater, and we’re seeing promoters stretch to find headliners, or stretch to make direct support acts into headliners.

Just like your truck driver buddy who keeps retiring, but then gets pulled out on the road again because the money is so good, Sturgill Simpson is getting enticed out of retirement to take one-off gigs that will probably pay of his grandkids’ mortgages for 90 minutes of work. Well, maybe a bit more with practice and travel time, but you get the point.

Perhaps Sturgill eventually will announce a tour to go along with these megafest headlining gigs. That’s kind of how the Turnpike Troubadours approached their return, first getting people to commit to big shows at Red Rocks and other places before filling out their calendar. But Sturgill doesn’t have to tour. Many people will gladly pay the megafest admittance to see him, and he can add more of these headliner gigs now that the precedent has been set.

Either way, just like Sturgill did when his album A Sailor’s Guide to Earth was nominated for the all-genre Grammy Album of the Year right beside Beyoncé, Drake, Adele, and Justin Bieber, he’s figured out a way to get himself to the forefront of music, despite his underdog status.

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