I’ve tried to write this article once before and it went nowhere, so this is a second shot at an idea that is somewhere down deep in my soul.

It’s about a stout country singer from the ‘80s and ‘90s who is mostly forgotten these days but has always meant a whole lot to me and the small fanbase of people, many in Florida, who love him and his music. 

My mom’s favorite song when I was a kid was “Swingin’” by John Anderson. Anderson was from Apopka, Fla., and whether you recognize him or not, there is a good chance you know his songs – ”Swingin’,” “Straight Tequila Night,” and “Seminole Wind” are just a few of the country classics Anderson launched to the top of the charts during his 20-year run as one of country music’s best songwriters and performers.

I mention Anderson now because he’ll be on the bill with JJ Grey & Mofro at Grey’s Blackwater Sol Revue festival at the St. Augustine Amphitheater in a few months. This Thursday he’ll be playing for his friends at the Big Cypress Indigenous Arts and Music Festival down at the Big Cypress Seminole Reservation. 

Every few years it seems like someone picks up the banner for John Anderson as one of our country’s truly great artists, and, inevitably, the people who have been here the whole time are appreciative, but it fails to really generate the kind of renewed interest the faithful think he deserves. A few years ago it was Dan Auerbach from the Black Keys. A few years before that James Taylor covered “Seminole Wind.” Before that it was John Rich from Big & Rich. Anderson cuts across genre lines that way. It’s fun and then John settles back into his routine – playing shows in beloved haunts and occasionally appearing on an RFD-TV show to play a few of his classics for a white-haired audience drinking coffee. 

But Anderson was never going to be the star George Strait or Alan Jackson would become. He was husky with wild-and-long blonde hair and a baritone that would rattle the water glass on your kitchen table. Sometimes he sang songs that bordered on novelty songs. Other times he sang foreboding, minor-key dirges that were as unsettling as thunderheads over a blackwater swamp. He lacked the wildness that Gary Stewart, also a Floridian-by-way-of-Kentucky and an active addict for his entire career, turned into a dark legend. He wasn’t quite Nashville, he wasn’t quite honky-tonk. He was, in a way, organic. He was uniquely ours. He still is. 

He had grown up a true Florida redneck – the type they used to call a Cracker – hunting turkeys on the land where Walt Disney World now stands and working as a plumber’s helper in the Central Florida area. A generational peer of Tom Petty, Lynyrd Skynyrd and a host of other Floridians who would find success in the ‘70s and ‘80s, he listened to Jimi Hendrix and the Rolling Stones before he got deep into country music. In true quirky Anderson fashion, he cites Merle Haggard’s Greatest Hits and Ray Charles’ (another Floridian) Modern Sounds in Country & Western Music as two of his favorite country records. He was in Nashville not long after, where he worked on building the new Grand Ole Opry building and landed a record contract in short order. 

He had success with several singles – including “I’m Just an Old Chunk of Coal (But I’m Gonna Be a Diamond Someday),” written by Billy Joe Shaver – before “Swingin’” would launch his career in a major way in 1982. The song is silly – it’s about sitting on a porch swing with his girlfriend (I’ve never had a girlfriend that didn’t loathe it). It’s fun, it’s catchy and, as is rare for Nashville stars, Anderson wrote it. 

Anderson’s records from that time are as good as country music in the ‘80s gets. He was already seamlessly blending folk, country and rock a solid decade before the term “Americana” would come into vogue – he covered Bob Dylan and performed songs by outlaw country writers like Shaver. He does honky tonk songs like “Would You Catch a Falling Star” that are absolutely perfect. He records “Wild & Blue,” maybe one of the greatest country songs of all time – and in doing so blends bluegrass, honky-tonk and pop effortlessly. Check out the albums Wild & Blue and I Just Came Home to Count the Memories. Absolute gold. 

He’d log a few more singles in the ‘80s before eventually leaving his label and beginning to fade away. It’s funny, too, because Anderson seems to always be just a little ahead of his time – the “new traditionalist” country he was playing would come into vogue in a big way in the late ‘80s with folks like Jackson and Clint Black and Ricky Van Shelton. But by that time Anderson just wasn’t getting songs on the radio like he used to. In so many ways, Anderson was the bridge between the outlaw country of the ‘70s and the neo-traditionalist movement of the ‘80s. He was authentically both while still being genuinely himself. 

But then a funny thing happened. Anderson would come back in a big way in the early ‘90s to his biggest success.

When Seminole Wind came out in 1992 it was perfect for the moment and also unlike anything else on country radio. The title track is an ode to the wild, natural Florida Anderson felt was slipping away to development and greed. The video, filmed in the Florida Everglades and on a Seminole Reservation with participation from the tribe (I believe it is Big Cypress, but I can’t confirm that), was in heavy rotation on CMT. 

To my knowledge there hasn’t been a country song – or any song – like it before or since. There are no other country songs about Florida, save for a novelty tune or two, and there definitely aren’t any that mourn the loss of its wild, swampy landscape to development. There is certainly not one that references “flood control” and draining wetlands. In a few minutes Anderson tells the whole sad history of Florida with an empathy and earnestness that keeps people coming back to it. It is, regardless of what Ron DeSantis and the zombified corpse of Lynyrd Skynyrd will tell you, Florida’s state song. It makes “Sweet Florida” and Stephen Foster’s “Old Folks at Home” look like utter dogshit in comparison. It is and will always be a banger, and I mean that as the highest praise I can lay on a single song. 

Not surprisingly, the label didn’t want to release it as a single. “I wanted to write a song about where I’m from that I could always be proud of, and, by golly, I was pretty sure I’d done it,” Anderson said in an interview. “But they said it was ‘too regional.’ We went to Portland, Oregon and played it, and they gave me a standing ovation. I called the record company the next morning and said, ‘It ain’t too damn regional. I’m demanding we put it out.”

Anderson’s other songs during this period are also quite good. “Straight Tequila Night” is a stone-cold classic and a surprisingly nuanced portrait of life at the end of the bar that still gets played by cover bands and karaoke legends. “When it Comes to You,” written by his friend Mark Knopfler of Dire Straits, is full of the resentment and menace that anyone who has ever suffered through a relationship-turned-sour can relate to. “Money in the Bank” has touches of “Swingin’” in its doe-eyed adoration of the object of the singer’s affection. “I’ve Got it Made” has a comfortable contentment that feels sweet without being overly sentimental. “Paradise” has the perfect mix of traditional and modern references that make it a much more real portrait of country life than anything from the “girl get in this here pickup truck” bro country era. 

These songs were the songs of my childhood. I’ve written a little bit about being a kid in Florida’s cowboy culture – riding in cutting horse competitions at places like the Adams Ranch in Fort Pierce and fishing along the banks of Lake Okeechobee at Port Mayaca – and Anderson’s music was ever-present during that time. 

In my mind as I write this I am right back there. There’s a horse arena and a cracked PA speaker announcing the riders. There’s a grill or a smoker sending the smell of peppers and onions across the pasture. At one horse trailer there’s a small TV playing the Florida Gators football game. At another, old Cuban men with names like Alecto are telling dirty jokes and sneaking sips of beer and rum. And “Seminole Wind” drifts across the entire scene, from the arena to the truck radios in the back. 

And then it was over. Anderson started his slow slide off the charts around the time his album Takin’ the Country Back came out and he would never quite recover. The genre made a hard turn from more traditional sounds toward vocal groups like Rascal Flatts and the hip-hop influenced sound of Big & Rich, who oddly enough, would champion Anderson and write songs for him even as their own glammy style pushed Anderson and many of his peers off the radio.

Anderson is something of an acquired taste.

I’m pretty good at turning my friends on to music I know they would love but might not seek out on their own, but no one has taken the bait on Anderson, ever. Even at the height of his fame he was able to make an impressive run on radio without really sticking in people’s consciousness. Like Gary Stewart, his voice is too weird and too complex to go down easy like George Strait does. Like Ronnie Van Zant, his politics are too idiosyncratic to fully belong to rightwing Nashville like Toby Keith or leftwing Americana like Jason Isbell. Like Tom Petty, his workmanlike ability to turn complicated emotions into tight radio singles precludes him from the tortured artist myth making of stars like Waylon Jennings. 

He’s just too damn Florida is what I’m saying – and America has never quite figured out what to do with pure, wild, uncut Florida. Kitsch from transplants like Jimmy Buffett, sure. But the actual weirdos that live here? Their palettes aren’t ready and probably never will be. It’s a mix of humor and sensitivity and righteous anger that just doesn’t sit well with the whole American thing. 

Dan Auerbach gave it a valiant go in 2020 with the comeback album Years, which was meant to position Anderson as a legend of great stature a la Johnny Cash via Rick Rubin. Auerbach did right by John – giving him good material and even getting Blake Shelton to make a guest appearance on the album, but it didn’t go far. A few years later the tribute album Something Borrowed, Something New saw artists like Sturgill Simpson, John Prine, Luke Combs and Tyler Childers taking on Anderson’s best material. It’s a great tribute album, but, again, it did little to move the needle or spark a major reassessment of Anderson’s place in the country music pantheon (Sturgill’s “When it Comes to You” is particularly great). 

So now JJ Grey, himself a Florida-loving native, is ready to take up the Anderson torch. He covered “Seminole Wind” for his 2024 album Olustee, and he regularly cites Anderson as one of his favorite musicians. They are, in many ways, kindred spirits, and the only two people I know who write lovingly about wild Florida. 

Grey’s music – and audience – may end up being a good fit for Anderson, but I find it hard to believe. Grey has definitely done a good job of turning the politically purple jam band crowd onto Florida conservation issues, but his music is more reminiscent of the boogie rock of Skynyrd or even Galactic. Anderson is a country musician, with the hat and all. He even recorded a song called “Country ‘Til I Die.” Nonetheless, I really hope it helps Anderson find a new audience, because if any country star from the ‘80s and ‘90s deserves a victory lap, he’s the one. 

What Anderson and Grey share, though, is a bittersweet tinge to their best songwriting. “Seminole Wind” is, ultimately, a lament. It’s a requiem for a version of Florida that Anderson knows is long gone and isn’t coming back. Likewise, in songs like “Lochloosa” and “Florida,” Grey clings to the last remaining pieces of Florida – the one his parents and grandparents told stories about, all while recognizing that developers will ultimately have their way with this enchanting place and turn it into more shopping malls, golf courses and gated communities. 

It’s a popular activity for Floridians – at least the ones in my family – to remember the beauty of the place they call home with reverent sadness. The same people that tend to be anti-nostalgic when it comes to people or pop culture break their hearts wide open for the rugged, humid, mosquito-ridden land that almost everyone else in the entire world couldn't wait to drain and develop. 

Ronnie Van Zant touched on this, too, when he put “All I Can Do is Write About It” on Gimme Back My Bullets. And perhaps that’s just it – the Floridians that remain have watched politicians, both Democrat and Republican, gladly capitulate to developers – even while making some efforts to buy back swampland (under state ownership). They have heard decades of lazy jokes from comedians about what a godforsaken place this is. They’ve seen commerce run roughshod over everything, pulling out palms and pines in favor of invasives and exotics. It’s a losing fight, loving Florida is. 

The state’s population grew by about 20 million people in the 20th century. Quite frankly, there just were never enough Floridians in the old Florida to make much of a difference against the crushing wheels of profit. As Anderson wrote in “Seminole Wind,” “progress came and took its toll.” And what a toll it was. 

So, what’s left? All we can do is write about it, sing about it and tell our stories to each other. And Anderson was perhaps the first to really do that in a big way. He was always Florida’s own, and he knows it.

“I sometimes think about what I’d have done if it didn’t work for me in Nashville,” Anderson said in an interview. “I guess I’d probably have waited a few years, and spent my life playing nightclubs back home in Florida. I’d have been in music, no matter what. And when I think about it, I think people down there would have liked my singing. I’m thinking I could have done okay.”