Originally Answered: What country musicians sing the best songs about heartache?
Tim McGraw's CD Let It Go has a few great cuts on being heartbroken and lonely...my favorite track on the CD is called "Whiskey and You." This is a really creative song, talks about the difference between Whiskey and a lover (My favorite line: "I drink because I'm lonesome and I'm lonesome because I drink.") He's pretty good in general, but his latest CD has a couple tracks that just really stand out. He is more contemporary country. Live Like You Were Dying CD also has some good heartbreak ballads...in my opinion, he gets better at these the older he gets.
A GREAT female singer who sings about loneliness and heartache is named Julie Roberts. She is younger, in her twenties. Country, but not too twangy. She has 2 CD's out, a self titled one that has a couple standout heartbreak tracks, called "Break Down Here" (about her leaving a man, she's driving a crappy car and hopes the car doesn't break down, because then she may), and "Wake Up Older," (about drinking herself drunk at night, and finding solace and comfort in a cool bottle and a stranger), and an album called "Men and Mascara" (the latter title track asks why men and mascara always runs, and there is another standout on their called "lonely alone" where she sings about how she'd rather be lonely by herself than lonely with her her man who has been ignoring her.) Also a really neat song, more mid-tempo, about how she finds out her man is cheating because the bed isn't made the way she makes it, called "Paint and Pillows."
Shania Twains second CD, but the first one most of the public knows, called "The Woman In Me" has some great slower heartbreak ballads, one called "Home Ain't Where His Heart Is", about a love dying, and one called "Is There Life After Love" about her regret for admitting an affair, and one of my favorites, "Raining On Our Love" where she looks back on a lover who left her for another, and she laments that she didn't know he was so lonely. Great ballads...maybe with her pending divorce she will write more songs like these.
Jason Aldean has a song called "Grown Woman" on his new CD "Relentless" that is pretty good.
Toby Keith has a couple good heartbreak and lonely songs...check out his 35 biggest hits CD. It's a 2-disc set, the first disc contains more of these heartbreak lonely songs. "I'm so happy I can't stop crying" is a good one.
If you want heartbreak from the Dixie Chicks, try an earlier CD called "Fly". Check out the last track "Let Him Fly" and "A Cold Day In July."
Stay away from big name artists like Keith Urban (he has a couple sad ballads, but they are pretty cookie cutter, and most of his stuff is happier), and Kenny Chesney, who sings a lot about beaches, as well as Martina McBride and Sara Evans among the ladies. You can find a few sadder tracks with them, but they aren't that good, and these artists mainly sing about family and faith. Not bad topics, but not ones that deal with hearbreak and loneliness.