He was born and raised in the South, but Jimmy Buffett is another die-hard Cubs fan. How did that happen? His journey from Southerner to Cubs fan is an interesting one. He explained it last year to Sports Illustrated when they wondered the same thing...

I ended up a Cubs fan because Chicago is one of the first major cities out of South where I had enough popularity to make a living. In doing so I wound in the company of (folk singer and songwriters) Steve Goodman and John Prine during that great folk era in Chicago. I was always a baseball fan because Mobile, Alabama had a lot of baseball heritage with the Aaron brothers and a minor league team. There was no major league teams in the South in those days. When I got to Chicago we worked at night. So Goodman would take me to Wrigley Field during the day and we would buy a ticket in the bleachers. I remember seeing Willie Mays play for the Mets against the Cubs. That was an amazing event for me. So those developing years musically for me I spent a lot of time in Chicago and at Wrigley Field.

In the mid-90s he began bugging Cubs management (many of whom were Buffett fans) to let him stage a concert at Wrigley Field. They finally relented, and during Labor Day weekend 2005, the weekend Katrina flooded the city of New Orleans, he got his wish. In honor of Ernie Banks, Jimmy Buffett played for two sold out Wrigley Field crowds. (Those concerts are available now on DVD)

What was that experience like for him?

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.