25 Saddest Country Songs That Will Break Your Heart Every Time

Can you be "just friends" with an ex? The legendary Patsy Cline answers that age-old question in this honky-tonk heartbreaker of a song.

This tearjerker tells the story of a young soldier and a high school waitress who meet and fall in love in the Vietnam war era. But tragically, the pair never get their happy ending.

Martina McBride's ballad about a little girl who is abused by her grandmother will have you reaching for the tissues and holding your loved ones a little closer.

Tim McGraw co-wrote this heart-rending song from the perspective of a fallen soldier who had written farewell letters to his loved ones in case he died in combat.

This award-winning duet tells the tragic story of two lovers who drank themselves to death after parting ways.

Vince Gill's writing of this spiritual song was bookended by two tragic deaths, that of country music singer Keith Whitley and that of Gill's own brother. It went on to win two Grammy Awards for Best Male Country Vocal Performance and Best Country Song.

This sad tune is about a man who copes with his brother's death by driving his old truck around town "'til all the pain's a cloud of dust."

This legendary song has stood the test of time and been covered by a wide range of musicians through the years. That includes Elvis Presley, who once introduced it as "the saddest song I've ever heard."

Alan Jackson's poignant song about the September 11 attacks struck a chord with the American public and won a Grammy Award for Best Country Song.

Rascal Flatts' heartbreaking song about a teenage girl named Sarabeth who is diagnosed with cancer will make you feel all the feels.

Perhaps one of the saddest songs in all of country music, George Jones' classic ballad tells the story of a heartbroken man who carries a torch for his lost love until the day he dies (literally).

This emotional pop ballad is for anyone who knows the pain of having loved and lost. Trisha Yearwood's "countrier" version is also not to be missed!

We all remember Whitney Houston's powerhouse rendition of the Dolly Parton-penned ballad. Dolly's original version is much softer but still just as beautiful and bittersweet.

This emotional story-song is about a woman who contracts AIDS following a one-night-stand. Reba McEntire later said she recorded the song in an effort to shed light on the issue and inspire people to be more compassionate towards those living with HIV and AIDS.

There are so many painful things about losing someone you love. If you ask Rascal Flatts, what hurts the most is never knowing what could have been.

It's been more than 60 years since Patsy Cline made this Willie Nelson-penned ballad a hit, but it still brings tears to the eyes.

How do we stay connected to our loved ones after they pass away? In this bittersweet ballad, Steve Wariner imagines there are holes in the floor of heaven that the angels can look through.

Johnny Cash's 2002 cover of the Nine Inch Nails classic "Hurt" was so powerful and compelling that songwriter Trent Reznor went so far as to say, "That song isn't mine anymore."

This bittersweet song tells the story of a widow who sees both herself and her beloved late husband in their young son.

This beautiful ballad reflects on the complicated feelings that come with having loved and lost, with heartfelt lyrics like: "And the good news is I'm better for the time we spent together, and the bad news is you're gone."