Alan Jackson

On May 25, 2002, Jackson earned his 20th No. 1 hit with "Drive (For Daddy Gene)."

The country legend celebrated with a sweet post about his new family member.

Country Music Hall of Fame-er Jackson has been performing live since starting a band after high school -- though, these days, he's performing on much bigger stages.

"Grateful is a gigantic understatement," Jackson shares on Instagram, promising a wedding picture drop soon. "Off to the islands with my husband!"

The style has had quite a comeback in recent years.

All 50-plus of 'em.

It was a historic moment.

On April 16, 2010, Jackson received a star on the Hollywood Walk of Fame.

The lakeside mansion sold for just over $6 million.

Which of these Alan Jackson hits tops your list?