Heartbreak on Valentine’s Day is a depressive playlist spanning the complex emotions of the bereft. These tracks do not adhere to any specific genre, so long as it has heartbreak as a central theme. Heartbreak songs come in many different forms, for example, The Police’s “Every Breath You Take”, off of their album Synchronicity, is a rather dark track about a possessive lover.

“Undying Love” by Nas is a powerful song about love and the crazy things that it can make you do, followed by a tragic ending. This song seems almost like a Shakespearean tragedy in the way it was written. Nas is a true lyricist.

No matter who you are or where you hail from, whether you sing soul or rap your hardest; love is a central theme in all of our lives. Heartbreak is a complicated and difficult state to conduct yourself within. These artists bared themselves raw to bring us emotion that feels palpable and possible.


This playlist is dedicated to those artists who poured their souls into their music. The heartbreak song is the great equalizer in music, bridging genres with emotion and experience.

This is the heartbreak playlist, available on Spotify (Heartbreak on Valentine’s Day)This playlist is best enjoyed on shuffle; the purpose is to be devoid of genre uniformity; love cannot be categorized.

Song: Every Breath You Take | Artist: The Police | Album: Synchronicity

Song: She’s Gone | Artist: Hall and Oates | Album: Abandoned Luncheonette

Song: Sorry Seems to Be the Hardest Word | Artist: Elton John | Album: Blue Moves

Song: Aint no Sunshine | Artist: Bill Withers | Album: Just as I am

Song: Thinkin’ Bout You | Artist: Frank Ocean | Album: Channel ORANGE

Song: Ivy | Artist: Frank Ocean | Album: Blonde

Song: Heartless | Artist: Kanye West | Album: 808’s and Heartbreaks

Song: Love Will Tear Us Apart | Artist: Joy Division | Album: Substance/The Best Of

Song: Cry me a River | Artist: Julie London | Album: Essential

Song: Don’t Speak | Artist: No Doubt | Album: Tragic Kingdom

Song: 50 Ways to Leave your Lover | Artist: Paul Simon | Album: Still Crazy After all These Years

Song: Irreplaceable | Artist: Beyoncé | Album: B’Day Deluxe Edition

Song: I Can’t Make You Love Me | Artist: Bonnie Rait | Album: Luck of the Draw

Song: I Will Always Love You | Artist: Whitney Houston | Album: The Bodyguard OST

Song: Tangled Up in Blue | Artist: Bob Dylan | Album: Blood on the Tracks

Song: Hikikomori | Artist: Crywank | Album: James Is Going to Die Soon

Song: Don’t Think Twice It’s Alright | Artist: Bob Dylan | Album: The Freewheelin’ Bob Dylan

Song: I Heard it Through the Grapevine | Artist: Marvin Gaye | Album: In the Groove

Song: ICE BOY | Artist: Corbin | Album: Mourn

Song: Black Lake | Artist: Björk | Album: Vulnicura

Song: Kettering | Artist: The Antlers | Album: Hospice

Song: Crown of Love | Artist: Arcade Fire | Album: Funeral

Song: Skinny Love | Artist: Bon Iver | Album: For Emma, Forever Ago

Song: I’ve Been Loving You Too Long | Artist: Otis Redding | Album: Otis Blue: Otis Redding Sings Soul

Song: Undying Love | Artist: Nas | Album: I am…

Song: Objects in the Mirror | Artist: Mac Miller | Album: Watching Movies with the Sound Off

Song: Sorry | Artist: T.I. ft. Andre 3000 | Album: Trouble Man: Heavy is the Head

Song: Teenage Love | Artist: Slick Rick | Album: The Great Adventures of Slick Rick

Song: Gone with You | Artist: Grey Kingdom/ Spencer Burton | Album: The Weeping Suns EP

Song: Nothing Compares 2 U | Artist: Sinead O’Connor | Album: I Do Not Want What I Haven’t Got