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10 Saddest Love Songs

Brad Paisley, Carrie Underwood, George Jones
Mike Coppola/Kevin Winter/Rick Diamond, Getty Images

Maybe someday scientists will explain why it feels so good to cry while listening to sad love songs. They might even decide it’s bad for us. Until then, we’ll keep listening to our favorite tear-jerking love songs. Some are a reminder that no matter how bad life gets, it can always get a little worse. Others illustrate exactly what we’ve gone through with a spouse, an ex-lover or current flame.

In selecting the saddest country love songs to include on this list, we reached back to find those that have endured years or even decades. Hits by George Jones and Hank Williams find their way to the top of this list, as do more modern sad love songs by Brad Paisley, Carrie Underwood and Joe Nichols. All 10 have a high probability of sending one to find a tissue or, in the case of some men, fake an allergy.

Mercury Nashville






There’s a fair argument to be made that this song doesn’t belong on a list of love songs. There’s also a fair argument to be made that it belongs at No. 1 on this list of sad love songs. Sugarland‘s Jennifer Nettles pours every ounce of pain she can remember into this raw and unsettling ballad. The video made it a much more personal experience. While ‘Stay’ is more of a breakup song than a love song, it is a sad story about love so we decided to keep it.


Vince Gill
MCA Nashville


‘When I Call Your Name’

Vince Gill



Few things are more difficult than loving someone who doesn’t feel the same. Vince Gill‘s song from 1990 perfectly describes that empty feeling in the heart one experiences when realizing he or she’s gone for good. “A note on the table that told me goodbye / It said you’d grown weary of living a lie / Your love has ended but mine still remains / But nobody answers when I call your name,” he sings.


Collin Raye
Epic Records


‘Love Me’

Collin Raye



The saddest country love songs always seem to end in a one-sided break up or death. Sometimes it’s both. Collin Raye tells the sweet story of one’s grandparents getting together before bringing us down with the inevitability of life: “If you get there before I do / Don’t give up on me / I’ll meet you when my chores are through / I don’t know how long I’ll be / But I’m not gonna let you down / Darling, wait and see / And between now and then, ’til I see you again / I’ll be loving you / Love, me.”


Tim McGraw
Curb Records


‘If You’re Reading This’

Tim McGraw



Tim McGraw‘s sad love song gets bumped a few notches up on this list by anyone who remembers his emotional ACM award show performance of the tune in 2007. It came at a sensitive time in American history and made a weeping mess of anyone with family members serving in the military, as well as half the population who didn’t. The combination of love, death and patriotism is sure to make mascara run.


Joe Nichols
Universal South


‘I’ll Wait For You’

Joe Nichols



Joe Nichols‘ biggest hits may have been more peppy tunes like ‘Tequila Makes Her Clothes Fall Off’ and ‘Gimme That Girl,’ but his fans know he’s as capable as anyone of delivering a poignant ballad. This song from 2006 hasn’t stood up to time as well as some other sad love songs on this list, but the circle-of-life story he tells affects everyone, especially parents: “I’ll wait for you at Heaven’s gate / Oh, I don’t care how long it takes / And I’ll tell Saint Pete I can’t come in / Without my love and my best friend / Oh, this ain’t nothin’ new / Sweetheart, I’ll wait for you.”


Arista Nashville
Arista Nashville


‘Just a Dream’

Carrie Underwood



While it’s true the video really turned this song into one of the saddest songs of all time, the story told in the lyrics would have held up nicely had it been released in a time without music videos. Carrie Underwood has proven to be a master at putting herself in stories that — as far as we know — have no connection to her personal life. She’s as convincingly heartbroken by the loss of a soon-to-be husband in this sad love song as she is vengeful in ‘Before He Cheats.’


Hank Williams


‘I’m So Lonesome I Could Cry’

Hank Williams



This sad love song is also one of the most poetic country songs of all time. A first time listener might miss Hank Williams’ pain as he sings, “Did you ever see a robin weep / When leaves began to die / That means he’s lost the will to live / I’m so lonesome I could cry.” Lack of radio play keeps this song from the top of the list, but the greatest compliment is that no country artist has seriously attempted covering Williams’ classic. No one has been big enough to fill those shoes.


Mark Wills
Mercury Nashville


‘Wish You Were Here’

Mark Wills



Mark Wills‘ song from 1999 is similar to Collin Raye’s ‘Love Me’ in that it tells a circle-of-life story. ‘Wish You Were Here’ is much more tragic as the main character loses a spouse suddenly, instead of after a long life together. “The weather’s nice, in paradise / It’s summertime all year and all the folks we know / They say, ‘Hello, I miss you so, wish you were here’ / Wish you were here,” Wills sings at the end as we wipe away our tears.


Brad Paisley
Arista Nashville


‘Whiskey Lullaby’

Brad Paisley Feat. Alison Krauss



This is the darkest song Brad Paisley has ever sang. It begins with “She put him out like the burnin’ end of a midnight cigarette,” and never recovers. Lyrically, the ballad is a masterpiece, and Alison Krauss‘s role as the female lead turns this sad love song into one that will stand the test of time. Paisley never reached No. 1 on Billboard’s charts with ‘Whiskey Lullaby,’ but won the CMA award for Song of the Year and sold over a million singles.


George Jones
Epic Records


‘He Stopped Loving Her Today’

George Jones



George Jones’ hit from 1980 tops our list of sad love songs while matching Paisley’s ‘Whiskey Lullaby’ in hopelessness and sadness, but his song has stood the test of time — whereas Paisley’s hasn’t yet had the chance to prove itself. ‘He Stopped Loving Her Today’ is one of the all-time greatest tearjerkers in any genre.


Next: The Saddest Songs in Rock

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