Jimmy Buffett

On Aug. 9, 2003, Jackson and Buffett hit No. 1 with "It's Five O'Clock Somewhere," from Jackson's 'Greatest Hits II' album.

Kenny Chesney joined him onstage for his most famous song.

On June 2, 2003, Jackson and Buffett teamed up to release the pint glasses-clinking ode "It's Five O'Clock Somewhere."

He sure knows how to enjoy the good life.

There's nothing we look forward to more through the long winter months than the prospect of a nice, relaxing (and preferably tropical) vacation.

Brad Paisley and songwriter Mac McAnally were to join Buffett later this month.

It's hard to believe he has never played on the hallowed stage.

The Boot sat down with songwriter Don Rollins to hear the story behind this now-classic tune.

Cheers!

The Boot takes inventory of the best tracks to blare as you're headed to, sitting on or just dreaming of the beach.