If there’s such a thing as an under-the-radar superstar, it’s Jimmy Buffett. He’s sold tens of millions of records, his concert tours sell out amphitheaters around the country in minutes and he’s released exactly one single since 1980 that charted on Billboard’s Top 100 since 1980. (He’s been more successful on the Country charts, especially as a guest artist recording with the Zac Brown Band and Alan Jackson.)
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Any comprehensive history of the biggest acts in rock and roll would be incomplete without Buffett receiving a chapter with color plates, but the odds are that whoever would be doing the writing would be content to leave him a mere footnote. He’s never exactly been what you might call a critical darling.
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That’s not something that seems to have bothered Buffett, who’s had to reconcile himself to a life of boating, flying airplanes, partial ownership of the Miami Dolphins, sold-out tours to massive crowds packed with people in goofy hats and loud shirts and other such consolation prizes. Still, when he took the stage at ACL Live on Wednesday night — a rare performance for a man who famously only plays on Tuesdays, Thursdays and Saturdays — it was easy to get a glimpse of the sort of performer Buffett might have been if the dice on his career had rolled slightly differently.

The venue was packed (tickets, priced at a below-usual cost for Buffett at just around $100, sold out in a brief two minutes the morning they went onsale) for the kickoff show on Buffett’s “Lounging At The Lagoon” summer tour. Buffett explained that the ACL Live date was something of a warm-up, “a big surprise in a little package,” as a theater show for an artist who usually plays venues with ten times the capacity. (ACL Live’s already-famous sightlines, incidentally, are still sufficient to overcome sitting behind people wearing eight-inch foam shark fin hats.)

For all the arena-readiness of Buffett’s band and material, though, the set scaled nicely to the ACL Live stage. The thing that’s easy to forget about the man’s material — especially the ones he wrote during his prime as a songwriter in the mid-70’s — is how personal and introspective it is.

After the ten-thousandth time you’ve heard a drunk warble “Margaritaville” at a karaoke night somewhere, it’s easy to lose track of the song’s lyrics, but Buffett’s greatest hit — as well as other songs from the 1973-1977 apex of Buffett’s writing career that he played on Wednesday night, including “Come Monday,” “Changes In Latitudes,” “A Pirate Looks At Forty” and “Son Of A Son Of A Sailor” — is one of the bleaker odes to a wasted life that has ever been sung-along to by a crowd of thousands. Often, that’s easily lost in the beach party context in which his music is usually framed.

At an intimate show — still a party (at one point, there were sixteen beach balls either on the stage or being passed around the crowd), but a much smaller one than usual — that aspect of Buffett’s work was easier to identify. Jimmy Buffett sings a lot of songs about wasted youth, feeling like you belong to another time, finding peace mostly in a bottle, being lost in a world that doesn’t understand you, and a contemporary world that makes you feel like you’ve drowned.

But his perspective on those things isn’t tragic, and he doesn’t romanticize them in the way that, say, Townes Van Zandt — who became a legend for writing about those same themes in a way that treats despair as glory — used to. Buffett’s songs about those things tend to lead to someplace that says, “But then I got drunk with some friends” or “at least I got a really good cheeseburger,” and celebrates those distractions from sadness, rather than plumbing the depths of despair.

Most Americans tend to do the same thing — but not the ones who pen paeans to the genius of tortured artists. Which helps explain both why Buffett’s flown under the critical radar for most of his career, and why there were so many people in Hawaiian shirts who just wanted to make fins with their hands and shout, “Salt! Salt! Salt!” during “Margaritaville.”

For his part, Buffett, too, seemed to treat the opportunity to make the show a more intimate sort of beach party as a special occasion. In between leading the sing-alongs, he treated the crowd to some unique moments and reflections of Austin – not just the usual shout-outs to Barton Springs (but, sure, those too), but also reminiscing about Jerry Jeff Walker, covering Nanci Griffith and playing a handful of songs that had been out of the perennially on-the-road band’s rotation for over a decade.

At this point in his career, Buffett’s obviously well-settled: he plays the nights of the week that he wants to, he’s able to enjoy the freedom to fly his airplanes and pack massive venues, he owns his own beer company, restaurant chain, and part of a football team. At 65 years old, any internal struggles he’s had over his lifetime about his role in music as a fan-favorite and critical non-entity have probably been resolved. Still, give him a few more nights in venues like ACL Live, and maybe even the critics will have to give him a second look.

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