Heartbreak can come in all shapes and sizes, but what we are talking about here today is that heartbreak that only a person once in love feels. That sit in bed all day, eat ice cream, and watch terrible Netflix documentaries kind of heartbreak. But, instead of contemplating texting your ex, I urge you to listen to my collection of heartbreak playlist essentials along with me. Trust me when I say that music is the ultimate comfort to pain, and pretty much anything is better than texting your ex.
- “A Case of You” by Joni Mitchell (2000)
I consider Mitchell the queen of heartbreak songs. The honesty in her lyrics is what draws audiences to her. She isn’t shy about her emotions; she’s going to let her listeners know how she is feeling. “A Case of You” is my favorite breakup song of all time, if not my favorite song of all time. The lyrics “you’re in my blood like holy wine” just hit all the right places during a time of heartbreak.
- “Lilac Wine” by Nina Simone (1966)
Simone’s vocals on this track are eerie yet beautiful. The combination of her voice with the piano’s echo offers a sense of solace to anyone trying to navigate a complicated ending to a romantic situation.
- “So Long, London” by Taylor Swift (2024)
Swift is no stranger to heartbreak, and she expresses her feelings with such vividness. Picking one song of hers for this playlist was hard, but “So Long, London” packs quite a punch. “Had a good run…but I’m not the one,” I mean, ouch.
4. “If I Were” by Vashti Bunyan (2005)
“He didn’t love me now it’s clear, if he had he would be here.” Is there anything more to say?
- “Answer Me, My Love” by Joni Mitchell (2000)
Off the same album as “A Case of You,” Mitchell’s cover of Nat King Cole’s hit reflects the heartbroken lover longing with the burning question, “Won’t you say that we can start a new?” A song for the broken who just want answers from the one person who can’t give it to them.
- “Pink in the Night” by Mitski (2018)
Mitski’s longing voice mixed with the simple instrumentals of this track echo in the heads of its listeners. Her repeating lyrics of “Can I try again, try again, and again, and again” mimic that of any longing lover reflecting on better times.
- “Tomorrow is a Long Time – Live at Town Hall, New York, NY – April 1963” by Bob Dylan (1971)
I am a huge fan of live versions of songs, and something as powerful as this track deserves to be listened to in that way. You can feel Dylan’s emotions through his singing on this track. From this, you can tell that he is one of the broken as well.
- “Let You Break My Heart Again” by Laufey (2021)
With the voice of an angel, Laufey yearns for her past lover in one of her earlier tracks. While she looks forward to happier days with the lyric, “Someday someone will like me like I like you,” she ultimately knows that if she even is placed in the situation again, she will allow them to “Let you break my heart again.”
- “Be My Mistake” by The 1975 (2018)
Matty Healy plus an acoustic guitar equals one of the band’s most raw and vulnerable songs in their catalog. “Be My Mistake” is just as the title implies, a song about wanting to do something that you know you shouldn’t with the one person you know you shouldn’t do it with
- “Dreaming My Dreams With You” by Cowboy Junkies (1988)
“Someday I’ll get over you.” Won’t we all? Margo Timmins has one of the greatest voices of her generation, its evocative nature reminds listeners of past memories, ones that may be difficult to bring back up.
- “Dragon New Warm Mountain I Believe in You” by Big Thief (2022)
Not the most traditional break-up song, but Adrianne Lenker’s haunting vocals mixed with the gentle, whimsical instrumentals create a reminiscent tone, one that urges its listeners to reflect on a better time in their life. One that makes them ask an old lover, “Hey, you, do you remember me, too?”
- “Stayaway – Recorded at Electric Lady Studios NYC” by MUNA (2019)
The original version of this song was great, but when MUNA decided to slow it down for their Spotify Singles session, they switched the whole meaning of this track. “Stayaway” reminds its listeners that “Leaving you was easy, now I gotta do what’s hard, I gotta stay away.”
- “Silver Springs – Live at Warner Brothers Studios in Burbank, CA 5/23/97” by Fleetwood Mac (1997)
I mean, does this even need a description? The ultimate breakup song that curses the one that caused you your pain (and quite literally as Stevie Nicks put a hex on the song’s inspiration and Fleetwood Mac guitarist and vocalist, Lindsey Buckingham), “Silver Springs” is all about revenge. As the track progresses, Nick’s anger rises and so does that of its listeners. Screaming this song at the top of your lungs is almost better than therapy.
Honorary mentions:
– “Glimpse of Us” Joji (2022)
– “Mystery of Love” by Sufjan Stevens (2017)
– “I Just Don’t Think I’ll Ever Get Over You” Colin Hay (2009)
– “Last Goodbye” Jeff Buckley (1994)
– “Diamonds and Rust” Joan Baez (1975)
– “Vampire Empire” Big Thief (2023)
