Jimmy Buffett

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

Buffett is on the mend after an unexpected hospital stay that forced him to postpone a show.

Buffett let fans know he expected to be back on stage soon.

It's a perfect match.

Doctors told Jimmy Buffett he needs to take the rest of the year off.

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

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

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

Danny Reagan gets a bit starry-eyed when he spots the singer, but then things take a turn for the worse.

Kenny Chesney joined him onstage for his most famous song.