Wow....
Thanks to all of you for these great suggestions!
Some are in iTunes already, some I know and forgot about, and more than a few I'd never heard of but will be checking out!
Steve, thanks for the links. My wife is a big Ricky Van fan!
My personal choice for saddest song ever? He Stopped Loving Her Today by George Jones.
Besides the country, a few in there that haven't been mentioned are:
Sad And Deep As You by Dave Mason
He Went To Paris by Jimmy Buffett
The Rose by Bette Midler
Seven Spanish Angels by Willie Nelson & Ray Charles
Time After Time by Cyndi Lauper
Family Line by Laurie Morvan
Again, everyone... THANKS!
(now keep the razor blades away from me, )