Alan Jackson

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

The country icon sang the classic song in honor of 9/11's 20th anniversary.

You know "Carlene" and "Just Another Day in Paradise," but did you know Phil Vassar also wrote these country hits for other artists?

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.

His ultra-high-end taste in property even extends to his vacation homes.

The lakeside mansion sold for just over $6 million.

Which of these Alan Jackson hits tops your list?

The Hollywood Walk of Fame features everyone from actors to radio personalities, and there are plenty of Nashville names enshrined there.

Jackson earned his first No. 1 hit on March 9, 1991, with the song "I'd Love You All Over Again," from his freshman 'Here in the Real World' album.