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Best Breakup Songs

Best Breakup Songs
Rick Diamond (2) / Mark Davis, Getty Images

Misery loves company, and a country music fan reeling from a breakup won’t have to search long to find a song to identify with. From Hank Williams to Taylor Swift, generations of Nashville’s top talent have penned tunes about dealing with the end of a relationship. Some songs in this collection of the best breakup songs are poignant, some are heartbreaking. And at least one is downright violent.

The 10 Best Breakup Songs were decided based on a song’s commercial success and ability to persevere through time. Reader input and staff opinion was also a factor in deciding which songs merit inclusion.


Curb Records
Curb Records
10

Tim McGraw, 'Please Remember Me'

From 'A Place in the Sun' (1999)
 
 

Tim McGraw plays the role of heartbreaker and heartbroken equally well. In this breakup song, he does both. 'Please Remember Me' is one of the superstar's finest vocal efforts. The emotional song from 1999 was a No. 1 hit and remains among his most powerful and well-written stories today.

 
EMI Records Nashville
EMI Records Nashville
9

Alan Jackson, 'So You Don't Have to Love Me Anymore'

From 'Thirty Miles West' (2012)
 
 

This Grammy-nominated single from 2012 didn't go on to become the singer's biggest commercial success, but it's difficult to argue the artistic integrity. Alan Jackson sounds hopeless on 'So You Don't Have to Love Me Anymore,' a song that finds a new perspective on the traditional breakup theme. Much like Tim McGraw in 'Just to See You Smile,' Jackson singer is still putting his ex-love first, even after the relationship has ended.

 
Mercury Records
Mercury Records
8

Toby Keith, 'Wish I Didn't Know Now'

From 'Toby Keith' (1993)
 
 

Toby Keith's early hit has withstood the test of time to become one of the best uptempo breakup songs ever. 'Wish I Didn't Know' tells the singer's sad story without being too heavy. It was a Top 5 hit for the country superstar, and to date is still one of his most effective lyrics ever.

 
Stay
Mercury Nashville
7

Sugarland, 'Stay'

From 'Enjoy the Ride' (2006)
 
 

Sugarland's 'Stay' doesn't reveal itself as a breakup song until the last verse, when the singer tells the man she's been seeing to stay home with his wife, because she is done begging for his love. Jennifer Nettles' emotional performance landed this song a place on the Top 100 Country Songs of All Time list. Like many songs in this breakup songs collection, 'Stay' was a huge hit that found a different way of looking at the classic breakup.

 
Before He Cheats
Sony Music Nashville
6

Carrie Underwood, 'Before He Cheats'

From 'Some Hearts' (2005)
 
 

Carrie Underwood's angriest hit finds the singer taking revenge on a man who cheated on her. Many may call the violent actions uncalled for or extreme, but those moving on after a nasty breakup may see it as therapeutic. Sure, no one endorses her actions, but the chart-topping song earned her numerous awards, including two Grammys. And it sure will make you feel better...

 
She Wouldn't Be Gone
Warner Music Nashville
5

Blake Shelton, 'She Wouldn't Be Gone'

From 'Startin' Fires' (2008)
 
 

"Yellow sunset slowly dipping down in the rearview / Oh, how she'd love to sit and watch you / I could have done that a whole lot more," Blake Shelton sings before the first chorus of 'She Wouldn't Be Gone,' his 2008 chart-topper. Aside from being a wonderful vocal performance and a terrific example of sharp songwriting, the song hits one on a deep emotional level. Shelton's pain is palpable as he searches for the woman who broke up with him. He proves that men, like women, also tend to go a little crazy when dumped.

 
Capitol Nashville
Capitol Nashville
4

Garth Brooks, 'The Dance'

From 'Garth Brooks' (1989)
 
 

This No. 1 hit would make a short list of the best Garth Brooks songs of all time. He approaches breaking up with a sense of gratitude and not an ounce of spite or anger. In 'The Dance,' the singer shows appreciation for the special times shared. If only every breakup could get to this point!

 
I Will Always Love You
RCA
3

Dolly Parton, 'I Will Always Love You'

From 'Jolene' (1974)
 
 

Dolly Parton's 1974 love song is both a love song and a breakup song, something unique to her spot on the Best Breakup Songs list. She's letting her man (in this case, duet partner Porter Wagoner) down softly, but still making it clear she's moving on. It's not steeped in misery or heartbreak, but Parton's No. 1 hit is time-tested and deserving of a spot on this list.

 
George Strait Give It Away
2

George Strait, 'Give It Away'

From 'It Just Comes Natural' (2006)
 
 

George Strait's brilliance as an interpreter of emotion is on full display in 'Give It Away,' his award-winning hit from 2006. The singer breezes through the breakup song with charismatic ease, but the subtle hurt in his voice reveals what's happening in his broken heart. Bill Anderson, Jamey Johnson and Buddy Cannon penned a beautiful story that -- like the singer -- has yet to show signs of age.

 
You'll Think of Me
Capitol Nashville
1

Keith Urban, 'You'll Think of Me'

From 'Golden Road' (2002)
 
 

Keith Urban created one of the more complex breakup songs of all time, although on the surface it seems the singer is singing a sweet goodbye to an ex-lover. It's clear with each lyric that he's dying inside, wishing she didn't find another man to run to. "And take your cap and leave my sweater / 'Cause we have nothing left to weather / In fact, I'll feel a whole lot better / But you'll think of me," he sings with aggression during the final chorus. 'You'll Think of Me' is one of Urban's best performances and hands-down the best country breakup song of all time.

 

Next: See the Top 100 Country Love Songs Ever

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