Tomorrow, he will start a four-night stand (May 13-14, 17-18) at The Pavilion at Old School Square in Delray Beach, Fla., not far from his home in Palm Beach. The reduced seating allows for around 850 people per show— seated in fenced four-person pods. Tickets for all four shows at the open-air venue sold out in around 10 minutes.
Buffett calls the concerts “spring training” for when his summer job resumes — playing full-capacity shows, rescheduled from last year — in July. He played (and filmed) two shows at the Belly Up Tavern in Solana Beach, Calif. for an invited crowd of 40 people in April, but, otherwise, the Delray Beach concerts will be his first in 14 months, and his excitement is palpable.
Buffett’s brand may be escapism, but he’s built his empire and life on two pillars that embrace responsibility. “I was always raised to be not a hater. And I was always raised with noblesse oblige — to give back if you’re lucky enough — thanks to my parents,” he says. “I just try to stick to those two things. I was taught not to hate in the segregated South. And I was taught to give back and I'm trying to teach my children the same thing.”
Sandwiched between paddling on the ocean to start his day and an omelette for breakfast, Buffett chatted with Billboard over Zoom about getting back on the road, his time as a Billboard reporter 50 years ago, and what a pirate sees when he looks at 75 (the answer includes a trip to Antartica).
What has your pandemic life been like?
I wound up places that I could. I wound up stuck. I mean, everybody's life stopped. I was 10 minutes from going to St. Bart's for the boat races that I do every year. And I wound up taking my kids, two of whom live in California, back, and I stayed [in Malibu] from March until May. And then I went home to Sag Harbor [N.Y.] and stayed there from May until September. And then I went down to St. Bart's, which at that time, there was no COVID there and I could go there.
I was working in all three places. I got little studios everywhere, so I was generating content and working on things and staying in touch with the band… The silver lining of this whole thing was I would have never spent that much time with my grown kids for the rest of my life. We're all with each other, but we're vagabonds, we're nomads and everybody's everywhere, but you know, six months with them was great.
Other than proximity, how did you pick The Pavilion at Old School Square for your re-entry to touring?
I’ve been looking at places I knew were making a really concerted effort to make sure everybody was safe. I saw this little place down in Delray, and I had friends that were recommending it to me. Dave, he's one of my contractors on my house, he’s a Telecaster player. A great guy. He goes to all the shows. I said, "You go and tell me what you think."
So fans have your contractor to thank?
Yes. We were looking at Key West, but Key West was sketchy. They had volunteer security (laughs). Yeah. I've been doing this awhile.
Because of restrictions, it’s one of the smallest audiences you’ve played for in decades. Does it take you back?
I think that you always have to look at when it wasn't like this, and when you had to play [small venues] and never forget that it can all go to h-ll in any minute, and never forget to duck. You know, those are the two things you had to [learn] coming out of clubs. And they stuck with me and, on occasion, you have to use those.
What were rehearsals with members of the Coral Reefer Band like, after not playing together for so long?
We utilized a little technology and so Mac [McAnally] and Eric [Darken] were in Nashville and they Zoomed into us and then Mike [Utley] and Robert [Greenidge] and I were together, but it was so much fun. I mean, that's my other family. It's like coming back from the war or something, you know, everybody's crying on the dock.
What do you do before a show to get pumped?
I'm usually going out and looking at the crowd first. I want to know who's out there before the lights go down. [After that], I can only see the first 10 rows [and] I’ve got to use that 10 to project to the rest of the people. So that's kind of my game plan.
How do you do that without people recognizing you?
There’s always a little sliver [through] the curtain back there. You can get over there and look out and see, but it's still so exciting to me to get up there and do it.
You stayed in touch with your fans, the Parrotheads, through the pandemic with weekly Zooms for first responders, the Nothin’ But Time virtual tour of vintage concerts and the video series (and resulting album) produced by your daughter Delaney, Songs You Don’t Know By Heart, which featured you talking about and acoustically performing lesser-known fan favorites. How did that come about?
Delaney, who’s a filmmaker, and a friend of hers from school, Dylan Orenstein, who works for us, were looking for programming or something that could keep people entertained. They said, “What about when you were playing, songs you didn't play and let fans do a set list?” They went online, maybe margaritaville.com or wherever, and said, “Make up a set list of what you want Jimmy to play. We'll see if we get him to play them through the pandemic.” We had like 10,000 set lists within the hour. Everyone voted, and we compressed them into a set list of songs you don't know by heart. And then Delaney filmed them. She was a tough interviewer (laughs).
In the episode with the song “Tin Cup Chalice,” you talk about leaving Nashville and going to live with Jerry Jeff Walker in Coconut Grove in the early ‘70s. How different would your life and sound have been if you'd never left Nashville to go Key West? [Editor's Note: Walker died Oct. 23, 2020.]
I thought about that [recently], because we're going down to do the tribute for Jerry Jeff in June in Luckenbach, because he was such an instrumental part of my career and my performing life. It was a critical time when I really needed a shot in Miami to break in and the guy booked it the wrong week. I was stuck with nothing to do and little money to do it. He took me in. We worked on his car while I waited for my gig and then after the gig was over, he said, “Let's go to Key West.” We got it in his ’47 Packard and he drove me down there. I thought to myself, “What if we had just gone to [bar] Alabama Jacks had a beer and gone back to Miami?”
It changed your life.
But you've always kept one foot in Nashville. Waylon Jennings, Merle Haggard, Lefty Frizzell all cut your music early on. And you’ve recorded with likeminded artists like Kenny Chesney, as well as Alan Jackson,Toby Keith, Martina McBride. Do you pay much attention to country now?
I do. When contemporary country took it to the beach, obviously we were a big part of that. And the other band was The Eagles. I am surprised that it's still staying on this long now. I figured they'd be over the beach… I tend to veer more to artists like Kacey Musgraves, Lukas Nelson, people like that that are not writing hits for radio. They're really writing, like Harlan Howard said, those three-chords-and-the-truth kind of songs.
Last May you released your first album of new material in seven years, Life on the Flip Side. It came in at No. 2 on the Billboard 200 and No. 1 on Top Country Albums. Do you still care about chart positions?
Yeah! C’mon! Who gets to do that? You know, if not for Lady Gaga, I would have [topped] them both, and that would have been fun. The best thing about it is I own the record company.
So you get every bit of the money!
Every bit of it!
You turn 75 on Christmas Day. So what does a pirate looks at 75 look like?
I'd like finish this rock and roll book I'm working on. It's based on when we went to Montserrat and did the  Volcano album. I’m making it fictitious, but it's based on that whole episode, which you can't believe the s--t that happened. I still can’t. There are so many stories and I file them away. It's a funny book, but it's a real rock ‘n roll book. It’s not a miserable experience, let's just say.
I kept writing some songs, and so instead of some 75th anniversary thing — I don't want to do that — I'd rather put another album out. I’ve got five songs now. I like what I'm doing. It's a little more kind of down island — authentic Creole and Trinidadian and Calypso kind of influences are in it.
Your writing days go way back. You’re Billboard’s most famous alumnus, even though you had to resign as a Nashville reporter when your first album came out in 1970. For our 125th anniversary, we ran a review you wrote of Isaac Hayes.
Yes, at Nashville’s Municipal Auditorium. You were very positive. Evaluate yourself as a critic.
I can never give anybody a bad review because I knew how hard it was to get up there. Now, there has to be something toxic that [a review] says, but I can never do it because I knew how hard it was. I know performers who are scared to death to get up there and still do it. And I go, “Why are you that scared to get up there?” I mean, you should be doing something else if you get scared to go up there. It’s one of the greatest joys you could ever have on planet earth to me.