Poets, Pirates & Parrots: Mac McAnally on Continuing Jimmy Buffett's Legacy, Collaborating with Kenny Chesney and More

Mac McAnally and Roger Guth’s Good Guys Win, first recorded by Jimmy Buffett for the 2006 Hoot soundtrack and finally released on McAnally’s 2020 album Once in a Lifetime, begins:

This hidden gem touches on a key notion that has pervaded Mac McAnally's almost-50 year career. Just like his mentor, Jimmy Buffett, and many of the artists that have gravitated towards him, McAnally often finds himself looking around in disbelief at the state of the world, before grinning and shrugging his shoulders. It might not be perfect, but as he warmly muses elsewhere on Once in a Lifetime, “It's almost all good”.

“You've seen the thing where people line up dominoes and they knock them down?”, McAnally muses during our conversation, “My thought in general about life is, if the dominoes start falling in a positive way, it's easy to keep them falling that way. If they start falling in a negative way, it's easy to keep them going in a negative way. So, I'm a realist in that I know that not everything is wonderful, but if I'm going to err on one side or the other, I'm going to lean towards the positive side - because the more people lean to the positive side, the more positive things actually get. Your perception can change reality in that way”.

He pauses, before adding, “It's probably an extension of the old Golden Rule. ‘You treat people the way you wanted to be treated yourself’...I've always found that people treat me generally well, and I was raised to respect everybody. In my lifetime, that's worked out to be a wonderful thing".

"I would rather spread positivity than negativity - and spreading something is unavoidable. Music is one of the only things in the world that can convert bad into good”.

It's not an exaggeration to say that Mac McAnally has been a cornerstone of country music since the '80's. He has become synonymous for his pivotal work alongside one of his best friends, Jimmy Buffett, and the way he embraced Buffett's breezy, glass-half-full outlook. Not only that, he was also in the studio helping to craft a host of game-changing songs, including Keith Whitley's ‘I'm No Stranger to the Rain’, Shenandoah's ’Two Dozen Roses’ and George Strait's ’Give It Away’.

When listening to McAnally's solo material, there's a expected warmth and amiability underlying every project, with the Alabama native delivering each lyric with a twinkle in his eyes.

He speaks with that same affable, genial nature, and is quick to deflect any praise or reminders as to his feats with a light-hearted, gently self-deprecating quip. For instance, when reflecting on one of the stand-outs from Once in a Lifetime, the wonderfully entertaining ‘First Sign of Trouble’, he jokes, “‘First Sign of Trouble’ was a fairly easy thing to do. It was tongue-in-cheek, and I wanted to showcase a little bit of guitar play. I'm not really a flashy guitar player, but ever since the CMA started giving me those Musician of the Year Awards, I felt like I should practice more, and try to do something to justify what they had done!”

McAnally has won the CMA Musician of the Year a record ten times, and shortly before we speak, he is recognised by the 2025 ACM Honors with the ACM Poets Award.

“That was an amazing thing”, he muses, “It was outside of my dream bandwidth that something like that would ever happen. In the beginning, the songs just fell out of me. I thought, ‘Well, that must be how people write songs. They just sing them like they've always known them’. I had three or four come out that way, and then eventually that didn't happen anymore, and I realized that sometimes you've got to work on them. I've been writing songs for five plus decades. Sometimes they're easy, sometimes they're hard, but I enjoy the process regardless of what it amounts to”.

Eleven solo albums, countless songwriting credits, and performances on the world’s biggest stages—yet even in 2025, McAnally keeps racking up fresh accolades and milestones. Aside from receiving the ACM Poets Award, in February, McAnally made his headlining debut at Nashville's revered Ryman Auditorium, as well as hitting the road alongside the Doobie Brothers with Jimmy Buffett's Coral Reefer Band.

Both that tour and the Ryman performance epitomised McAnally's primary impetus these days - to ensure the music of his close buddy, Jimmy Buffett, lives on for many years to come. At the Ryman, for instance, McAnally had Buffett's beloved guitar positioned centre-stage, with the setlist peppered with Parrothead favourites.

McAnally fondly reflects, “I had his guitar, and we set up a microphone for him, just in case he wanted to show up. We still do that in the Coral Reefer shows. We leave Jimmy's microphone up, because nobody can replace him, and we would never try to do that. He's not a replaceable character. We're just trying to carry on his musical legacy as best we can".

The duo famously met after Buffett picked up a copy of McAnally's self-titled 1977 album, and, when writing the fast-emerging musician a note, boldly declared, “We're going to be friends”. McAnally went on to become a key member of the Coral Reefer Band, and worked with Buffett throughout his career, helping to pen iconic hits such as ‘Changing Channels’, ‘Breathe In, Breathe Out, Move On’ and ‘It's My Job’.

McAnally pays homage to the late Gulf and Western trailblazer, who passed away almost two years ago to the day. “He took me under his wing really early, and he believed in me before I believed in myself. He had enough confidence for a large crowd of people, and I was not born with a great deal of it, so I wouldn't be on any stage - or having this conversation with you - had he not taken the step of believing in me first.

"I owe the guy a lot, and my last conversation with him was, ‘I want you to keep the party going, keep the music rolling around’. So I do. I don't take the responsibility as anything negative, I think of that as a blessing that he asked me to do it, because I love the guy. He was my big brother”.

McAnally worked closely with Buffett on what would ultimately be his final album, Equal Strain on All Parts (although McAnally confirms there is more posthumous music on the way). With Buffett keen to remain the life of the party, McAnally explains that he was one of the few people who knew the severity of his condition.

“It wasn't general knowledge through the crew, the band and the studio folks that he was as sick as he was, because he never wanted to contribute to anybody being sad on any day”, McAnally wistfully muses, “He wanted to make people happy, but I knew. He and I are very close, and we were talking back and forth about these songs, but he never spoke of anything like, ‘This is my last record’...He never surrendered to this illness. Even when I went to say goodbye to him, he was like, ‘We're going to Paris in November. Get ready’. And we knew we were saying goodbye...So it was never spoken of as his last record. But, honestly, I knew, because of how hard he worked on these songs, that he saw it as that”.

He goes on, “I always compared Jimmy more to a painter than a traditional songwriter...He was not a perfectionist. He would have great ideas, but he was like, ‘This is what we did today. We'll do something else tomorrow’, in the same way they talk about Picasso."

"I'm probably a little bit more of a detailed, finished carpenter guy, whereas Jimmy would have a great idea fast, and say, ‘Here, do your thing to this’. We were a good team in that way. "

"With this particular batch of songs on Equal Strain, I've never seen him work that hard to make them as good as they could be. So I think he was conscious that, ‘This is my last statement. This is what I'm going to leave people with’. He got some really fine work in there too. ‘Bubbles Up’ is as nice of a song as he ever had anything to do with”.

‘Bubbles Up’ was inspired by Buffett taking part in a notoriously challenging Naval Academy training test, where the trainee is dropped from 30 foot in a helicopter chamber, to simulate crashing into the sea in an aircraft. The way to escape and find your way back to the surface, as Buffett learned, is to follow the ‘bubbles up’. The Margaritaville founder transformed this into a pertinent metaphor for life.

McAnally is joined on his own test - to continue Buffett's legacy - by a number of like-minded artists, such as Zac Brown Band and Kenny Chesney. The trio performed a moving tribute to Buffett at the 2023 CMA Awards, with McAnally and Chesney then joining James Taylor to pay homage to their pal at the Rock and Roll Hall of Fame.

“There are certainly worse people to emulate than Jimmy”, McAnally highlights, “He always treated everybody well. He wanted us to stay in the same hotels as him, and we flew on his private plane. We were so spoiled, because he wanted the people that he loved to be around. On most tours, the star stays somewhere and gets there a certain way, and everybody else gets there on a bus...Jimmy was like, ‘We're going to play music, we're gonna have fun. We're only gonna play three shows a week, because I want to experience all these cities’. So it was never a gruelling tour...We got the benefit of that wonderful way to work”.

Chesney - who recently joined McAnally again, this time at his own headline Ryman show - has based much of his music on Buffett's sunny-side-up approach to life. “Kenny, like Jimmy, is a sweetheart. He's a good soul. He's a positive force all over the world, and he's patterned much of how he does his business after the way Jimmy did his, so there was a natural affinity. Jimmy grew up down on the salt water - he was always a boat guy. He was always a sailor. Whereas Kenny and I grew up in landlocked poverty in Appalachia. He's said it a million times that ‘I wouldn't have a boat, and I wouldn't know about the water if it wasn't for Jimmy Buffett’”.

Chesney recorded one of the gems in McAnally's discography, ‘Back Where I Come From’, as well as the familial ode, ‘Down the Road’, which consequently propelled both into mega-hits. “The first song of mine he recorded, ‘Back Where I Come From’, was about my hometown, which had 900 people in it. When I wrote that song about painting your name on the water tank, in my mind, there were only 900 people that would get anything out of that song. But when Kenny heard that song, he was from Luttrell, Tennessee, and he, of course, saw his water tank with his name on it. And it turns out there's small town people all over the country that had a water tank with their name on it - I'm just not smart enough to consider the universality of songs, I was writing just from my own personal experience. But sometimes, if you write what's deep in your own heart, there is universality in that”.

He concludes, “Kenny saw something that I didn't see in that song, and he sold 25 million copies of it, so I'm obviously grateful that he did! It was a great part of Jimmy's show - Jimmy and I always sang that song, because Jimmy was born in Mississippi, and we always looked at each other every night, saying, ‘I'm an old Mississippian’. I got to travel hundreds of places that I never would have traveled if it weren't for riding a shotgun with Jimmy. So all of that is a nice circle of life for me”.

McAnally is quick to credit the likes of Buffett and Chesney for the success he now enjoys, speaking about his songwriting style as so intuitive that it almost feels accidental, and making light of his generational, CMA-Award-winning guitar-playing.

He depicts himself as a supporting cast-member, someone who is happy to give the assist and watch someone else bask in the glory. But McAnally is a cornerstone of the genre we know and love, both a songwriting maestro and an instrumental virtuoso. While he doesn't want the level of fame Buffett and Chesney have achieved, that doesn't mean we can't still celebrate him as the luminary he truly is.

It's evident Mac McAnally never sought out the spotlight, but ever since he - somewhat reluctantly - found it, he has strived to reflect that glow onto others. Whether he is using his platform to pay homage to his mentor and partner-in-crime, or to simply become a beacon of light for those tussling with the darkness, McAnally never wants to be seen as the hero the listener longs for in that song he penned with Buffett for Hoot all those years ago.

Even if McAnally refuses to take on this mantle, at the very least, he and his fellow poets, pirates and Parrotheads are proof that, every once in a while, the good guys do, indeed, win.

For more on Mac McAnally, see below:

All photos by David McClister