Alan Jackson

Grief, regret and hopelessness are three major themes in this countdown of the most depressing country songs of all time.

Every road has to come to an end.

For some, living with chronic illness is simply a fact of life.

It came to him in the middle of the night.

It was a less divisive time in country music, and even though we bickered about what is and isn't "real country," the assaults were less personal.

You have to see these outlandish homes to believe them.

It's not as easy as it looks.

These country artists are flying high!

Alan Jackson wasn't even second in line!

You'll recognize some of these amazing celebrity houses instantly.