35 Best Songs about Heartbreak

Everyone has experienced the pain of heartbreak at some point in their lives.

The universal topic is one that songwriters have covered since the first tune was written. Artists’ penchant for messy relationships adds to the seemingly endless amount of material they have for the songwriting process.

Whether you are going through a breakup or are working through feelings of loneliness, here is a list of songs about heartbreak.

Stay – Rihanna ft. Mikky Ekko

Featuring a lone piano and Rihanna’s powerful vocals, this emotional single resonates with anyone going through a heartbreak. The intimate lyrics switch back and forth between moments of empowerment and questions of personal worth as the nuances of relationships are explored. Nashville songwriter Mikky Ekko wrote ‘Stay’ and contributed backup vocals during the track’s recording.

Related: See more great inspirational songs about loving yourself.

Apologize – Timbaland ft. OneRepublic

OneRepublic frontman Ryan Tedder has a powerful falsetto range, and he shows off his vocal abilities with the hit ‘Apologize.’ Though the band is generally billed as a pop group, that didn’t stop Hip Hop/R&B mogul Timbaland from stepping in and taking on the role of producer. The song features lyrics reflecting on a painful breakup and learning how to move on.

Related: Feeling guilty? Check out these songs about apologizing.

All Too Well – Taylor Swift

Appearing on Taylor Swift’s Red album, the original version of ‘All Too Well’ debuted at number one on the Top 100 after its release. It’s an eye-opening, no-holds-barred account of her public relationship with actor Jake Gyllenhaal. Though she reveals intimate details about their relationship in this sad song, he has openly stated he has no hard feelings regarding T. Swift.

Related: Calling all Swifties! Listen to the best of Taylor Swift.

Lover, You Should’ve Come Over – Jeff Buckley

Late songwriter Jeff Buckley had a special talent for combining dark lyrical concepts with vulnerable vocal deliveries. Though he is best known posthumously for his rendition of Leonard Cohen’s ‘Hallelujah,’ his original song ‘Lover, You Should’ve Come Over’ deserves its own recognition as a complex breakup song full of raw emotion and honesty.

Related: Go to our playlist of songs about breaking up with someone.

Don’t Speak – No Doubt

Gwen Stefani pushed the boundaries of how female artists should present themselves in the ’90s by doing pushups on stage during performances and rocking out with her male-dominated band. Despite her much-loved bravado, she had moments of vulnerability and softness with hits like ‘Don’t Speak.’ This single features Stefani reminiscing about her former relationship with bassist bandmate Tony Kanal.

Related: Don’t close the door on our playlist of songs about leaving someone.

Someone Like You – Adele

Perhaps one of the most popular heartbreak songs, Adele belts into the mic over minimalist instrumentation in her single ‘Someone Like You.’ In two short days, she recorded the track at an LA studio, utilizing only a grand piano and a one-man production crew (Semisonic band member Dan Wilson). Though her delivery emotes a longing for her lost relationship, she focuses on moving on and wishing “nothing but the best” for her ex.

Related: Check out this list of songs about dealing with exes.

Go Your Own Way – Fleetwood Mac

Rocky relationships were a common theme among band members of legendary Fleetwood Mac. Frontwoman Stevie Nix dated guitarist Lindsey Buckingham, and other bandmates got together with each other throughout the band’s tenure as well. ‘Go Your Own Way’ was one of their many hits, which required Nix to sing the song countless times. Buckingham wrote it to her as a poignant message regarding his thoughts on their past relationship.

Related: Hit the road with these songs for traveling.

It’s Too Late – Carole King

Carole King was a pioneer of folk music. Using only her voice and minimalist instrumentation, she’s penned some of the most moving singer/songwriter pieces in contemporary music. ‘It’s Too Late’ was written quickly and focuses on finding the strength to move on after realizing a relationship you put a lot of work into is ending.

Related: Get encouraged with these uplifting breakup songs.

Nothing Compares 2 U – Sinéad O’Connor

Pop icon Prince wrote this song but didn’t release it. Instead, he gave it to a band, The Family, to record in the mid-’80s. Sinead’s manager suggested she record a cover of it years later, and it became one of the few hits she had during her time spent in the spotlight. Though her version of ‘Nothing Compares 2 U’ won her a Grammy, the Irish artist quickly faded into the background of the industry because commercialized fame wasn’t the lifestyle she wanted to have.

Related: Head over to this playlist of songs about regrets.

Hey, That’s No Way to Say Goodbye – Leonard Cohen

Cohen’s version of the popular moody love song ‘Hey, That’s No Way To Say Goodbye’ finds him juggling his need for a relationship and his lack of ability to settle down. Cohen recorded the song in 1967, around the same time singer Judy Collins recorded it for her own album. Other artists who’ve cut the track include Roberta Flack and Ian McCulloch.

Related: This song features on our playlist of songs about people leaving.

I Will Survive – Gloria Gaynor

After being let go by the infamous recording label, Motown producer and songwriter Dino Fekaris found himself writing this scathing song for Sun Records in his living room. He vowed to himself he wouldn’t let this roadblock stop him. He began producing artists independently, and the first one he worked with, Gloria Gaynor, had the honor of singing the classic song ‘I Will Survive.’

Related: Feel empowered with these songs about survivors.

You Oughta Know – Alanis Morissette

Alanis Morissette’s confessionalist single ‘You Oughta Know’ highlights her anger at an ex who never gave her closure. It’s an emotionally rich pop-rock song that was part of a string of hits from her 1993 album Jagged Little Pill. Supposedly, the controversial song was about her rocky relationship with Full House star Dave Coulier, though he’s never officially confirmed or denied this himself, and neither has Alanis.

Related: Seek revenge on our playlist of songs about vengeance.

Somebody That I Used to Know – Gotye

Gotye received a record amount of radio airplay with his eclectic single ‘Somebody That I Used to Know,’ and is still regarded as one of the most popular breakup songs. Pairing electronic sounds with relatable lyrics, he sings about the ending of a relationship and not even being able to recognize the person he once loved anymore. The song features duo-style vocals by Kimbra, a singer-songwriter from New Zealand.

Related: We all mess up. Check out these songs about shame.

We Are Never Ever Getting Back Together – Taylor Swift

Taylor Swift’s high-powered pop tune features bouncy vocals and heavy electric guitars driving home the in-your-face message, “We are never, ever getting back together. The songwriter continues her tried-and-true tradition of writing about her exes with this single. Nobody knows for sure who the song’s about, but she penned it regarding a former on-again-off-again beau.

Skinny Love – Bon Iver

It was rumored that Bon Iver’s ‘Skinny Love’ was about frontman Justin Vernon’s former girlfriend known as “Christy.” However, after being interviewed, he denied writing the song about one person. Instead, it’s a more general song about being in a relationship that is unhealthy than allowing that relationship to affect future ones.

Related: Take off with these songs about moving on.

I Can’t Make You Love Me – Bonnie Raitt

Known for her slide guitar prowess and masterful blues delivery, Bonnie Raitt sings about a lover she knows she’s losing in ‘I Can’t Make You Love Me.’ She knows he’s moving on but wants just one more night with him before they call it quits. Several artists have covered the tune over the years, including Boys II Men and ’80s pop sensation George Michael.

Related: Listen to our playlist of other good songs about wanting someone you can’t have.

The Scientist – Coldplay

Songwriter and Coldplay frontman Chris Martin penned this tune about his terrible luck with relationships. In the song, he relates it to a scientist who gets so focused on his work he neglects his girlfriend. Martin stays busy touring and recording with his band, which has negatively affected his past relationships, including a failed marriage to actress Gwyneth Paltrow.

Related: Get all the feels with these songs about feelings.

The Tracks of My Tears – Smokey Robinson

Drawing on personal heartache for Miracle’s song ‘The Tracks of My Tears,’ bandmate Smokey Robinson wrote it while wondering one day if a man could cry enough that tears would leave marks on his face. It’s a highly emotional, gut-wrenching song that appears on their 1965 album, Going To a Go-Go.

Related: You’ll need a tissue when listening to these songs about crying.

We Belong Together – Mariah Carey

Hip Hop/R&B mogul Jermaine Dupre produced this record-setting Mariah Carey track featured on her album, The Emancipation of Mimi. The song features Carey singing about an ex who she feels should still be with her because they truly belong together. The single won her multiple Grammys and set listener records on the radio. She and Dupre recorded the entire song in one session that lasted less than 24 hours.

Related: It’s hard to let go. Listen to our playlist of staying together songs.

Don’t Think Twice, It’s All Right – Bob Dylan

Bob Dylan’s conversational ‘Don’t Think Twice, It’s All Right’ has him flipping the script on his girlfriend, who left him to study in Italy. In the song, he leaves her. The easygoing lyrics read like a private conversation Dylan is having with himself. The Four Seasons would later cover this track during the peak of their popularity.

Related: Don’t think too hard about listening to these songs about overthinking.

Dreaming with a Broken Heart – John Mayer

John Mayer’s heartfelt lyrics leave interpretation up to the listener. The song’s imagery centers around encountering an ex in a dream and all the emotions stirred up from the experience. The subject matter for ‘Dreaming with a Broken Heart’ deals with everything from loneliness and unrequited love to the uncomfortable aftermath of a relationship.

Related: See our playlist of heartache songs.

Since U Been Gone – Kelly Clarkson

Popstar and American Idol winner Kelly Clarkson scored a big hit with her single ‘Since U Been Gone’ from her famous album Breakaway in 2004. The cheeky yet empowering song features Clarkson singing about an ex who did her wrong and her vow never to make the same mistake twice. The single almost didn’t make the cut for the album because the singer wasn’t a fan of the acoustic version she heard when she was listening to demos. Good thing she didn’t cut it because most lists of the best heartbreak songs feature this one!

Related: Sing along with the top karaoke songs of all time.

Ex-Factor – Lauryn Hill

Lauryn Hill’s ‘Ex-Factor’ tackles heavier issues in unhealthy relationships. Using the lyrics to elude to the abuse she endures, she sings of her lover in the present tense, who treats her terribly, yet she can’t seem to walk away. Some lines find her trying to rationalize with him for better treatment as she attempts to make the toxic romance work.

Un-Break My Heart – Toni Braxton

This powerful ballad has Toni Braxton belting out lyrics, yearning for a romance to return to the way it was. Though her ex has caused her unbearable pain with his leaving, she still wants him to come back. She is begging him to “unbreak” her heart and return things to the way they were before he walked out on her.

Related: You might enjoy these songs about old love.

Before He Cheats – Carrie Underwood

Country singer Carrie Underwood’s brooding, angry single ‘Before He Cheats’ might leave male listeners a bit uncomfortable and female listeners with a few new ideas as she sings about the destruction she imparts on her lover’s car when she finds out he’s cheating on her. Though Underwood delivers a convincing performance, she has been quoted in interviews saying many times she’s nothing like the character she portrays in her songs.

Related: Find similar songs on this playlist of cheating songs.

Say Something – A Great Big World ft. Christina Aguilera

Popstar and The Voice judge Christina Aguilera fell in love with this song while watching a dance competition and hearing it for the first time. Unlike many of her other heavily mixed tracks, this rare stripped-down ballad features Christina singing with A Great Big World about the darkness of broken relationships. She performed the song live with the group and on an episode of The Voice.

Margo’s Waltz – Lloyd Cole

Alt-Pop singer Lloyd Cole released this track on his early ’90s album Don’t Get Weird On Me Babe. It’s a relatable number for anyone who has had to go through the aftermath of a messy breakup. From changing your routine, so you don’t run into the person to learning how to sleep alone at night, Cole tackles the touchy subject of heartbreak in his poetic track ‘Margo’s Waltz.’

Heartless – Ye

Headline-making rapper Kanye West, who also goes by the nickname Ye, was incredibly proud of his track ‘Heartless’ due to its intricate, poetic lyrics. They paint a volatile picture while the classic R&B beat adds to the song’s tension. The breakup song appears on his 2008 album, 808’s & Heartbreak.

Torn – Natalie Imbruglia

Pop singer Natalie Imbruglia scored her only hit in the US with her folksy song ‘Torn.’ An honest account of her state of mind after a painful breakup, Imbruglia uses lyrics to sing about her world being turned upside down and being unable to get dressed in the mornings. After becoming a steady hit in the UK, it reached the top spot in America and stayed there for several weeks.

Related: Go back in time with this list of 90s karaoke songs.

Need You Now – Lady A

No list of sad breakup songs is complete without this one. Lady A found themselves back in the country music spotlight with their emotional hit ‘Need You Now’ focusing on not being able to move on from a former lover. The trio sings about all the ways one might turn back to the familiarity of a former relationship because they are afraid of being alone. Featured on their sophomore album, ‘Need You Now’ spent a record 31 weeks in the top ten of the Top 100 Billboard chart.

Related: You won’t be alone with these songs about being lonely.

Pictures of You – The Cure

The Cure had a knack for writing dark, moody songs, and ‘Pictures of You’ is no exception. Frontman Robert Smith was inspired to write the song after reading the Dark Power of Ritual Pictures essay. After reading it, he destroyed many of his personal photos and videos and wrote the song ‘Pictures of You.’ Days later, he regretted destroying so many personal memories, and the listener can feel his overwhelming pain in the track.

Related: See more classic songs about feeling guilty.

Losing You – Solange

Beyonce’s sister Solange Knowles is a talented singer-songwriter in her own right, and she finds herself confronting a failing relationship in her song ‘Losing You.’ She asks her boyfriend for honesty as she tries to figure out if the relationship is over or if there’s anything left worth fighting for. This was her first release after signing to indie label Terrible Records.

Related: Trust us, you’ll love these songs about trust in relationships.

When I Was Your Man – Bruno Mars

Bruno Mars vowed not to put a ballad on his 2012 record, Unorthodox Jukebox. But after penning ‘When I Was Your Man’ during a co-writing session, he knew it belonged on the album. Comprising nothing but a piano and his voice, he reflects on the one that got away before he became famous. The confident writer once told an interviewer he had never been as nervous about releasing a single as he was when he debuted the heartbreaking ballad.

If I Ain’t Got You – Alicia Keys

Though this tune deals with heartbreak, it has also served as an inspirational message for many. UK athlete Kelly Holmes used the tune as fuel to win races during the Olympics. Many contestants on voice competition shows have covered the song as well. Keys wrote it about the tragic plane crash that killed R&B singer Alicia Keys in 2001.

Related: You’ll love the best romantic songs of all time.

Tears Dry on Their Own – Amy Winehouse

Appearing on her Back to Black album in 2006, like most of the tracklisting ‘Tears Dry on Their Own’ details Amy Winehouse’s damaging relationship with actor Blake Fielder-Civil. Though they ultimately got married, the songs on the Back To Black album were written during a time when he left her and went back to a previous girlfriend.

More songs about heartbreak:

  • Just a Friend – Biz Markie
  • Ghost – Justin Bieber
  • Tangled Up in Blue – Bob Dylan
  • I Will Always Love You – Whitney Houston
  • I’d Rather Go Blind – Etta James
  • Nothing Breaks Like a Heart – Mark Ronson ft. Miley Cyrus
  • Stay with Me – Sam Smith

Photo of author

About Ged Richardson

Ged Richardson is the Founder and Editor-in-Chief of ZingInstruments.com. He has been featured in Entrepreneur, PremierGuitar, Hallmark, Wanderlust, CreativeLive, and other major publications. As an avid music fan, he spends his time researching and writing about new and old music, as well as testing and reviewing music-related products. He's played guitar in various bands, from rock to gypsy jazz. Be sure to check out his YouTube channel, where he geeks out about his favorite bands.

Read more