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20 country songs that will definitely make you cry

In country music, there's no denying that some of the best songs are the saddest songs. Few genres are better at exploring themes of love, loss, and heartbreak than country music, and the decades are positively replete with tearjerking tunes that have managed to stand the test of time.

Flip through the slideshow below for 20 of country's saddest songs, from classics like "I'm So Lonesome I Could Cry" to newer songs like Jason Isbell's "Dress Blues." 

1 of 20

"Whiskey Lullaby," Alison Krauss and Brad Paisley

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This 2004 tearjerker written by Jon Randall and recorded by Alison Krauss and Brad Paisley can leave even a tough guy in tears. It's a song about love lost, alcoholism, and taking your own life that's got a truly haunting vibe thanks to Paisley and Krauss's harmonies. 

2 of 20

"You Were Mine," The Chicks

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There are many country songs about heartbreak, but "You Were Mine" really puts a fine point on the devastation of a messy divorce and everyone it impacts. But because the lyrics were so poignant and relatable, the song was a breakout success for the Chicks in 1998. 

3 of 20

"The Grand Tour," George Jones

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Fans have their own theories about how the couple in "The Grand Tour" came to be separated — Did the wife die, or did she just leave him? — but there's no denying that this 1974 George Jones classic is an absolute heartbreaker. 

4 of 20

"I'm So Lonesome I Could Cry," Hank Williams Sr.

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This 1949 ballad is equal parts plain-spoken and plaintive, which somehow makes it seem even more sad. Many fans regard "I'm So Lonesome I Could Cry" as one of country music's saddest tunes, and that's due in large part to Hank Williams Sr.'s uniquely melancholy delivery. 

5 of 20

"She Thinks His Name Was John," Reba McEntire

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Even though the illness is never explicitly mentioned, "She Thinks His Name Was John" is a song about the AIDS crisis. The song was controversial upon its 1994 release and serves as a stark reminder of the impacts that HIV was having on the country at the time.

6 of 20

"She's Got You," Patsy Cline

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Patsy Cline's catalog is positively replete with devastating tunes, from "Crazy" to "I Fall to Pieces." But "She's Got You" remains one of country music's most enduring break-up tunes thanks to Cline's melancholic vocals and the timeless lyrics from songwriter Hank Cochran. 

7 of 20

"Misery & Gin," Merle Haggard

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With "misery" in the title, it's clear that this 1980 Merle Haggard tune isn't going to be upbeat. It's arguably the greatest among many country songs about a man who's trying to drink his mind off an old flame. 

8 of 20

"He Stopped Loving Her Today," George Jones

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Widely regarded by many as the saddest song in country music history, "He Stopped Loving Her Today" is about a man who holds a candle for his lost love until the day he died. Jones was at first skeptical of the song, which he called "morbid," but it later became his signature tune and was even performed by Alan Jackson at Jones's funeral service in 2013. 

9 of 20

"The Dance," Garth Brooks

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The definition of "bittersweet," "The Dance" by Garth Brooks is about the pain that comes with love and a life well-lived. "Our lives are better left to chance, I could have missed the pain," Brooks sings. "But I'd have had to miss the dance." Wise words for us all to remember. 

10 of 20

"Don't Take The Girl," Tim McGraw

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This tear-jerking tune was a No. 1 hit for Tim McGraw in 1993. It follows a young man named Johnny as he and his childhood love encounter multiple terrifying scenarios, including being mugged at gunpoint and pregnancy complications. The song ultimately has a happy ending, but don't be surprised if you shed a few tears along the way. 

11 of 20

"Concrete Angel," Martina McBride

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Released in 2003, this devastating tune by Martina McBride tells the story of a little girl who is experiencing serious child abuse. The girl is ultimately murdered by her abusive parent, and McBride sings with deep emotion about an afterlife where the "concrete angel" is embraced in heaven. 

12 of 20

"If I Die Young," The Band Perry

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Released in 2010, this song by the Band Perry about the tragedy of those who've died too young immediately resonated with country fans who'd lost loved ones. The song was a fast No. 1 hit on both the Billboard Country Airplay and Adult Contemporary charts. 

13 of 20

"If Tomorrow Never Comes," Garth Brooks

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This song, about living life to the fullest and imagining a world where "tomorrow never comes," was a smash-hit for Garth Brooks in 1989. The song's message about making sure that your loved ones really know how you feel is seriously poignant. "'Cause I've lost loved ones in my life, who never knew how much I loved them / Now I live with the regret that my true feelings were never revealed," he sings. "So I made a promise to myself to say each day how much she means to me / And avoid that circumstance where there's no second chance to tell her how I feel." 

14 of 20

"Over You," Miranda Lambert

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Co-written by Miranda Lambert and her ex-husband Blake Shelton about the loss of Shelton's sister in a car accident when she was a teenager, "Over You" is one of Lambert's most poignant ballads. 

15 of 20

"Holes In The Floor Of Heaven," Steve Wariner

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This song about love and loss imagines a world in which raindrops are the tears of our lost loved ones flowing from heaven. It was a major hit for Steve Wariner in 1998, peaking at No. 2 on the Billboard Hot Country Songs chart. 

16 of 20

"Go Rest High on That Mountain," Vince Gill

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"Go Rest High on That Mountain" is a deeply personal song for Vince Gill, who started writing it after the tragic death of fellow country star Keith Whitley. Gill finished the song following the loss of his brother, and it has since become one of his signature tracks — and one of country's greatest mourning songs. 

17 of 20

"Travelin' Soldier," The Chicks

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Written by Bruce Robison, "Travelin' Soldier" tells the story of a young, unnamed soldier headed off to the war in Vietnam who starts corresponding with a waitress he meets in a small-town diner before he's shipped off to war. The poignancy of the song was overshadowed dramatically by the impact of frontwoman Natalie Maines's comments about the War in Iraq shortly after the song hit No. 1 in 2002. 

18 of 20

"Seven Spanish Angels," Willie Nelson and Ray Charles

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The lyrics of this Willie Nelson and Ray Charles duet are a richly woven tapestry, focused on a story of love, loss, and a gunfight with the law involving two ill-fated outlaw lovers with a chorus of angels praying above them. 

19 of 20

"There You'll Be," Faith Hill

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This Faith Hill anthem, which appeared on the soundtrack for the film Pearl Harbor, is a tribute to those we've lost — and the impact they've had on our lives. It's the kind of song you listen to while smiling through tears, thinking of your lost loved ones. 

20 of 20

"Dress Blues," Jason Isbell

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Appearing on his first solo album after leaving the Drive-By Truckers, "Dress Blues" is about a young man who is killed in the war in Iraq. "Nobody here could forget you, you showed us what we had to lose," Isbell sings plaintively. "You never planned on the bombs in the sand, or sleeping in your dress blues." 

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