Now, the Wrigley stand -- a pair of concerts over Labor Day weekend 2005 -- is available on the double-DVD set Jimmy Buffett: Live at Wrigley Field.
"You always find time for baseball," Buffett said recently in an exclusive interview with MLB.com. "I think probably a day at the park with my dad was one of the great influences on me in trying to get a job where I could get a balance of work and play time. And it was lucky enough that it worked out that way."
Luckily for Parrotheads, Jimmy Buffett -- Live At Wrigley Field has it all covered. The two nights of concerts at the 92-year-old ivy-covered ballpark marked the first concerts in the yard's well-documented history.
And to borrow a phrase from the most famous Cub in history, "Mr. Cub" Ernie Banks, "Let's play two."
The double-disc set is approximately 2 hours, 45 minutes long and contains 26 songs, plus bonus footage and some surprises.
"One of the fun things was that it just seems like it only happened yesterday," Buffett said.
"The first thing that came to mind for me was how perfect the weather was, how good the band played, and the amazing fan reaction, and always, above everything, the actual realization that you were doing this in Wrigley Field and nobody had ever done it before.
"It kind of overwhelmed me when I went back to look at the video. It was certainly overwhelming at the time when you're up there playing. You know, I haven't played too many historic gigs, but this one surely was."
Buffett said he conjured the initial idea for the Chicago concerts while "in some bar in Wrigleyville" and that it took "probably 10-12 years of talking to people in the Cubs' organization who were also Parrotheads" to pull it off.
Once it happened, Buffett said, "it went so fast," but the success of the concerts, along with similar results from the September 2004 two-show run at Fenway, had Buffett and his Coral Reefer Band buzzing.
"I look back at it and it's an amazing thing to think about, that we've actually done that," Buffett said. "And looking back at the many years I've been able to do this and looking at some of the highlight moments of an amazing run, these two certainly stand out as some of the finer moments I've spent on the stage."
The Red Sox would probably agree.
When Buffett and his band arrived at Fenway on Sept. 10, 2004, the Red Sox were mere weeks away from the stunning playoff run that culminated with a World Series sweep of the St. Louis Cardinals and Beantown's first championship since 1918.
But at the time, a lot of fans were probably expecting something to go wrong and for the Sox to experience one of the infamous near-misses that plagued those 86 years in the Hub without a ring.
Enter Buffett, who had a plan.
"Being the shameless performer that I am and being observant enough to know about [Red Sox history], I mean, I remember the  ball through [Bill] Buckner's legs pretty well," Buffett said.
"Everybody was talking about it, and we did a little skit in the show -- we were just trying to do our part to get rid of the 'Curse of the Bambino,' and lo and behold, the Red Sox come back on that amazing comeback [after being down 0-3 in the American League Championship Series] after we played there.
"We, of course, were just trying to do our part in the show. Many, many people were doing many, many other things to rid Fenway of that curse, but everybody seemed to think that all of a sudden we had a major part to do with it when we played Fenway.
"A lot of things had been tried before and this is the first time anybody had ever gone into the park on a stage and done it like we did it. So if it was part of the ridding of the curse, which it seemed to do, well, I'm happy to have done it."
Buffett has been happy to do tons of other things lately, too.
In addition to garnering Grammy nominations in 2004 and 2005 and charting the first No. 1 record of his career with 2004's License To Chill, Buffett has added "movie producer" to a resume that already includes "best-selling author" and "radio personality."
But as he says, there's always time for baseball in Buffett's life.
He's a proud Little League dad, he's a co-owner of the Class A Fort Myers (Fla.) Miracle, and he's always got something on his mind besides music when he's on the road.
"One of the great by-products of being on tour is the fact that we're always in a major city somewhere," Buffett said.
"And there's pretty much always a baseball game."