Heartache is a familiar theme in music.
Each song on this list is included based on its lyrical content, and most of them celebrate the darker side of love: heartaches, breakups, lying, cheating, unhealthy obsessions and general relationship dysfunction.
From Demi Lovato’s devastating ballad “Still Have Me” to Beyonce’s heartbreaking “Irreplaceable” and everything in between, ccroll to the end of this post for the playlist, then up the volume and get ready for a good cry.
This article has been updated.
Eminem feat. Rihanna, “Love The Way You Lie”
Most Heartbreaking Lyric: “Just gonna stand there and watch me burn? / That’s alright because I like the way it hurts / Just gonna stand there and hear me cry? That’s alright because I love the way you lie.”
Lana Del Rey, “The Greatest”
Most Heartbreaking Lyric: “I miss Long Beach and I miss you, babe/ I miss dancing with you the most of all/ I miss the bar where the Beach Boys would go/ Dennis’ last stop before Kokomo.”
Lady Antebellum, “Need You Now”
Most Heartbreaking Lyric: “Another shot of whiskey can’t stop looking at the door / wishing you’d come sweeping in the way you did before. / And I wonder if I ever cross your mind. / For me it happens all the time.”
The Platters, “Smoke Gets In Your Eyes”
Most Heartbreaking Lyric: “Now laughing friends deride / tears I can not hide / Oh, so I smile and say / When a lovely flame dies / smoke gets in your eyes.”
Miley Cyrus, “Slide Away”
Most Heartbreaking Lyric: “Once upon a time, it was made for us (For us)/ Woke up one day, it had turned to dust/ Baby, we were found, but now we’re lost/ So it’s time to let it go.”
Mariah Carey, “Love Takes Time”
Most Heartbreaking Lyric: “Couldn’t see that I was blind to let you go? / I can’t escape the pain inside / Cause love takes time / I don’t wanna be here, I don’t wanna be here alone.”
The 4 Seasons, “Big Girls Don’t Cry”
Most Heartbreaking Lyric: “(Silly girl) ‘Shame on You, you’re crying in bed? / (Silly girl) ‘Shame on you, you told me lies!’ Big girls do cry.”
Rod Stewart, “Maggie May”
Most Heartbreaking Lyric: “I know I keep you amused but I feel I’m being used. / Oh Maggie, I couldn’t have tried anymore. / You lured me away from home just to save you from being alone / You stole my heart and that’s what really hurt.”
Wham! Feat. George Michael, “Careless Whisper”
Most Heartbreaking Lyric: “I should have known better than to cheat a friend / and waste a chance that I’ve been given. / So I’m never gonna dance again / the way I danced with you.”
Bonnie Tyler, “Total Eclipse of the Heart”
Most Heartbreaking Lyric: “Once upon a time I was falling in love. / Now I’m only falling apart. / There’s nothing I can do / total eclipse of the heart.”
Beyonce, “Irreplaceable”
Most Heartbreaking Lyric: “So since I’m not your everything (irreplaceable) / How about I’ll be nothing? / Nothing at all to you. / Baby I won’t shed a tear for you / I won’t lose a wink of sleep / Cause the truth of the matter is / replacing you is so easy”
Ariana Grande, “Thank U, Next”
Most Heartbreaking Lyric: “Even almost got married/ And for Pete, I’m so thankful/ Wish I could say, ‘Thank you’ to Malcolm/ ‘Cause he was an angel.”
Usher, “Burn”
Most Heartbreaking Lyric: “Think it’s best we go our separate ways. / Tell me why I should stay in this relationship / when I’m hurting baby, I ain’t happy baby? / Plus there’s so many other things I gotta deal with. / I think that you should let it burn.”
Gilbert O’Sullivan, “Alone Again (Naturally)”
Most Heart Breaking Lyric: “When you’re shattered / left standing in the lurch at a church / Were people saying, ‘My God, that’s tough / She stood him up. / No point in us remaining. / We may as well go home’ / As I did on my own / Alone again, naturally.”
The Tony Rich Project, “Nobody Knows”
Most Heartbreaking Lyric: “I carry a smile when I’m broken in two. / And I’m nobody without someone like you. / I’m trembling at night and nobody knows it but me.”
Ashanti, “Foolish”
Most Heartbreaking Lyric: “Baby why you hurt me leave me and desert me? / Boy, I gave you all my heart and all you do is tear it up.”
Gloria Gaynor, “I Will Survive”
Most Heartbreaking Lyric: “It took all the strength I had not to fall apart. / Kept trying hard to mend the pieces of my broken heart. / And I spent oh so many nights just feeling sorry for myself. / I used to cry / now I hold my head up high.”
Fergie, “Big Girls Don’t Cry”
Most Heartbreaking Lyric: “The path that I’m walkin’ I must go alone. / I must take the baby steps ’til I’m full grown, full grown. / Fairy tales don’t always have a happy ending, do they? / And I foresee the dark ahead if I stay.”
Sinead O’Connor, “Nothing Compares 2 U”
Most Heartbreaking Lyric: “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?”
Carly Simon, “You’re So Vain”
Most Heart Breaking Lyric: “You said that we made such a pretty pair / and that you would never leave. / But you gave away the things you loved and one of them was me.”
Whitney Houston, “I Will Always Love You”
Most Heartbreaking Lyric: “Bittersweet memories / that is all I’m taking with me. / So goodbye. Please don’t cry. / We both know I’m not what you need.”
Marvin Gaye, “I Heard It Through The Grapevine”
Most Heartbreaking Lyric: “I know that a man ain’t supposed to cry, but these tears I can’t hold inside. / Losing you would end my life you see, cause you mean that much to me.”
Ace Of Base, “The Sign”
Most Heartbreaking Lyric: “How can a person like me care for you? / Why do I bother when you’re not the one for me? / Is enough enough?”
Timbaland feat. OneRepublic, “Apologize”
Most Heartbreaking Lyric: “You tell me that you need me then you go and cut me down. / But wait, you tell me that you’re sorry. / Didn’t think I’d turn around and say / that it’s too late to apologize. It’s too late.”
Adele, “Rolling In The Deep”
Most Heartbreaking Lyric: “We could have had it all, / rolling in the deep. / You had my heart inside of your hand / and you played it to the beat.”
Boyz II Men, “End Of The Road”
Most Heartbreaking Lyric: “When I can’t sleep at night without holding you tight. / Girl, each time I try I just break down and cry. / Pain in my head. Oh, I’d rather be dead, / spinning around and around.”
Demi Lovato, “Still Have Me”
Most Heartbreaking Lyric: “Everything around me shattered/ All the highs are now just low/ But it doesn’t even matter/ ‘Cause I’d rather be alone.”
Jewel, “Foolish Games”
Most Heartbreaking Lyric: “These foolish games are tearing me apart. / And your thoughtless words are breaking my heart. / You’re breaking my heart.”
Toni Braxton, “Un-Break My Heart”
Most Heartbreaking Lyric: “Un-break my heart. / Say you’ll love me again. / Undo this hurt you caused when you walked out the door / and walked out of my life.”
Mariah Carey, “We Belong Together”
Most Heartbreaking Lyric: “The pain reflected in this song ain’t even half of what I’m feeling inside. / I need you, need you back in my life, baby. / We belong together.”