80"It's Too Late" by Carol King
Most Heartbreaking Lyrics:
"There'll be good times again for me and you / But we just can't stay together, don't you feel it, too? / Still I'm glad for what we had and how I once loved you."
79"Picture" by Kid Rock, featuring Sheryl Crow
Most Heartbreaking Lyrics:
"I put your picture away / Sat down and cried today / I can't look at you while I'm lying next to her."
78"Cuts Like a Knife" by Bryan Adams
Most Heartbreaking Lyrics:
"I took it all for granted / But how was I to know/ That you'd be letting go."
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77"Don't Wanna Lose You Now" by Gloria Estefan
Most Heartbreaking Lyrics:
"I don't wanna lose you now / We're gonna get through somehow / I don't want to loose you now or ever."
76"What It Takes" by Aerosmith
Most Heartbreaking Lyrics:
"Tell me that you're happy that you're on your own / Tell me that it's better when you're all alone / Tell me that your body doesn't miss my touch / Tell me that my lovin' didn't mean that much / Tell me you ain't dyin' when you're cryin' for me."
75"No Air" by Jordin Sparks, featuring Chris Brown
Most Heartbreaking Lyrics:
"But how do you expect me / To live alone with just me? / 'Cause my world revolves around you / It's so hard for me to breathe."
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74"Please Don't Go Girl" by New Kids on the Block
Most Heartbreaking Lyrics:
"Girl, you're my best friend / Girl, you're my love within / I just want you to know / That I will always love you."
73"End of the Road" by Boyz II Men
Most Heartbreaking Lyrics:
"When I can't sleep at night / Without holding you tight / Girl, each time I try / I just break down and cry."
72"I Have Nothing" by Whitney Houston
Most Heartbreaking Lyrics:
"Don't you dare walk away from me / I have nothing / If I don't have you."
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71"Cry Me a River" by Justin Timberlake
Most Heartbreaking Lyrics:
"You were my sun / You were my earth / But you didn't know all the ways I loved you."
70"Too Little, Too Late" by Jojo
Most Heartbreaking Lyrics:
"So let me on down / 'Cause time has made me strong / I'm starting to move on / I'm gonna say this now / Your chance has come and gone."
69"Before He Cheats" by Carrie Underwood
Most Heartbreaking Lyrics:
"I might've saved a little trouble for the next girl / 'Cause the next time that he cheats / Oh, you know it won't be on me."
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68"Foolish Beat" by Debbie Gibson
Most Heartbreaking Lyrics:
"And when we said goodbye / Oh, the look in your eyes / Just left me beside myself without your heart / I could never love again now that we're apart."
67"You Oughta Know" by Alanis Morissette
"'Cause the love that you gave that we made / Wasn't able to make it enough for you / To be open wide, no. / And every time you speak her name / Does she know how you told me / You'd hold me until you died."
66"Linger" by The Cranberries
Most Heartbreaking Lyrics:
"I swore I would be true / And honey so did you / So why were you holding her hand? / Is that the way we stand? / Were you lying all the time? / Was it just a game to you?"
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65"Nothing Compares 2 U" by Sinead O'Connor
Most Heartbreaking Lyrics:
"It's been so lonely without you here / Like a bird without a song. Nothing can stop these lonely tears from falling / Tell me baby, where did I go wrong?"
64"We Are Never Ever Getting Back Together" by Taylor Swift
Most Heartbreaking Lyrics:
"Then you come around again and say / Baby, I miss you and I swear I'm gonna change, trust me / Remember how that lasted for a day?"
63"Whose Bed Have Your Boots Been Under?" by Shania Twain
Most Heartbreaking Lyrics:
"And whose lips have you been kissin'? / And whose ear did you make a wish in? / Is she the one that you've been missin', baby? / Well whose bed have your boots been under?"
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62"Broken Vow" by Josh Groban
Most Heartbreaking Lyrics:
"Tell me again / I want to hear / Who broke my faith in all these years? / Who lays with you at night / When I'm here all alone / Remembering when I was your own."
61"Take a Bow" by Rihanna
Most Heartbreaking Lyrics:
"Don't tell me you're sorry 'cause you're not / Baby when I know you're only sorry you got caught."
Kelly O’Sullivan is the senior editor for The Pioneer Woman and manages the website’s social channels, in addition to overseeing content strategy and news.
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