Alan Jackson

Learn the specific reason he started wearing a cowboy hat.

He's one of country music's all-time greats.

"Since Alan writes so many of his own songs, I never would’ve guessed he’d be the first person to cut one of my songs ..."

The singer scored his record 21st No. 1 song.

Available now is a special 2-DVD set from Alan Jackson!

Did we get it right?

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

This country superstar's career has yielded some truly unforgettable moments.

On Aug. 5, 1995, Jackson had a big reason to celebrate.

Double entendre, puns, unexpected turns of phrase -- the best country stars and songwriters don't shy away from a literary device.

This kind of high living comes with a pretty high price tag attached.

He's joined the ranks of the REALLY big league.