My Ultimate Breakup Mixtape

By Natalie McCarty

’Tis the season for post-Christmas heartbreak, as the newly single find themselves navigating the New Year’s Eve landscape. If you’ve secured your midnight kiss, kudos (feel free to bookmark this for future reference). For those still in the throes of heartache and in desperate need of a musical companion to their melancholy, I present the evil twin of last week’s article, “Date Night: A Reel Guide to Romance” — “My Ultimate Breakup Mixtape.”

Inspired by one of my favorite films, Stephen Frears’ High Fidelity, I’ve curated a list of my top songs that have been on constant replay during every breakup I’ve ever weathered — a fact well-documented by my Spotify wrapped stats. Though it has been a hot second since my last breakup and I don’t plan on having any new ones in the near future, this compilation of songs remains my tried and true, having gotten me through every era.

If there’s one enduring truth, it’s the inseparable connection between “Silver Springs” and the complexities of heartbreak. The haunting melody, penned by Stevie Nicks and immortalized by Fleetwood Mac, stands as an anthem of raw emotion and introspection that resonates deeply with the pangs of lost love.

For those unacquainted, Nicks crafted “Silver Springs” amidst the tumult of her relationship with Lindsey Buckingham, the band’s guitarist. The lyrics, a poignant reflection of the pain and remorse accompanying a love that couldn’t withstand the test of time, possess a unique ability to stir the soul. Nicks’ emotionally charged vocal delivery adds a haunting quality, reaching into the depths of heartbreak — a sentiment personally amplified in my own experience.

The lyrical canvas is painted with vivid imagery, where the metaphorical “silver spring” symbolizes tears or a moment suspended in time. This imagery enriches the emotional narrative, delving into the theme of unresolved love and the ache for a bygone relationship. The chorus, with lines like “Time cast a spell on you, but you won’t forget me,” encapsulates the enduring emotions following a breakup.

I openly admit to singling out this song as a favorite, one of the rare covers I’ve shared. It holds a special place, etched into my repertoire as one of the only two songs I’ve mastered on the piano, even serving as an audition piece. Deliberately, I’ve chosen to align myself closely with this song, making it a part of my identity. A point that served me well when, famously, an ex-boyfriend of mine candidly confessed that, to this day, he cannot ever hear the song without thinking of me (and of me singing it). Score!

Anyway, if there is only one thing to be true, it will always be: “I know I could’ve loved you, but you would not let me / I’ll follow you down ’til the sound of my voice will haunt you / Was I such a fool? / You’ll never get away from the sound of the woman that loves you.”

“Black” by Pearl Jam isn’t just their standout track from their acclaimed album Ten; it stands as one of the greatest songs ever crafted. Growing up under the influence of my mother’s love for Pearl Jam, I proudly claim the title of their biggest fan. Choosing a favorite among their catalog is a significant declaration for me, and with a song as flawless as “Black,” I have no reservations about making that public proclamation.

This track takes on an even more profound significance during moments of heartbreak. It skillfully encapsulates the depth of emotions — missing, longing, yearning, and the desire to reconnect with someone from the past. Eddie Vedder’s vocals are a poignant expression, comparing all five horizons to revolving around his absent lover’s soul. The transition into the chorus, where his bitter hands chafe beneath the clouds of what once meant everything, is simply beautiful. The lyrics vividly paint a picture of all the memories turned to black, the love lost that has cast his world into darkness, tattooing every aspect of his being. Singing along to this song becomes a cathartic experience, but it reaches its pinnacle during the bridge, where Vedder’s screams become an exorcism of heartbreak: “I know someday you’ll have a beautiful life / I know you’ll be a star / In somebody else’s sky / But why / Why / Why can’t it be / Why can’t it be mine.” This raw expression of longing and resignation elevates the song to a level of emotional intensity that resonates deeply.

Jeff Buckley’s “Forget Her” is eternally entwined with a period when heartbreak rendered me so shattered that I succumbed to three days of uninterrupted sleep, with this song assuming the role of my poignant lullaby.

The entire album Grace embodies the essence of an angsty stroll in the rain, tearfully cascading down one’s cheek. While selecting a definitive favorite from the album proves challenging, “Forget Her” undeniably claims a significant place in my heart. Every time it’s haunting melody graces my ears, a paralyzing chill courses down my spine. Whether triggered by the echoes of past arguments or the fresh wounds of a recent breakup, the song leaves an indelible imprint of regret that resonates hauntingly.

Nothing screams Carrie and Big like “Hello It’s Me” by Todd Rundgren. While the enchanting dance to “Moon River” and their iconic episode naturally comes to mind, the moment I hear “Hello It’s Me,” I can’t help but think, “Oh, hi Big!”

Although it may not top the list as the most breakup-centric track, there’s an undeniable quality of yearning for what was once had or nearly grasped that elevates it to the status of a breakup favorite for me. Beyond its thematic resonance, the song stands as a beautifully composed piece in its own right.

“Fade Into You” by Mazzy Star undeniably secures its place among my top five favorite songs ever, owing to its uniquely haunting, devastating, yet romantic quality.

Each time the melodic strains of the song begin, an audible breath escapes me. It serves as a portal to a plethora of memories, spanning from intimate apartment dances and heated arguments to strolls through the autumnal streets of New York and languid moments on a Washington Square bench, observing the people passing by in the summer. The song encapsulates late-night drives, the anticipation of high school formals, the vibrancy of college parties, the tenderness of first kisses, and the liberating spirit of road trips — all flooding my mind with vivid recollections. “Fade Into You” weaves a tapestry of emotions, making it not just a song but a resonant soundtrack to the chapters of my life.

Of all the songs on the list, the Goo Goo Dolls’ “Iris” stands out as the one with the greatest potential for multigenerational resonance. The instant allure begins right from the opening chorus, and it seems nearly impossible not to be captivated. Who doesn’t know “And I’d give up forever to touch you / ’Cause I know that you feel me somehow / You’re the closest to heaven that I’ll ever be / And I don’t want to go home right now?”

I can’t think of a person who isn’t familiar with this song, yet it often seems overlooked and omitted from movie soundtracks. Let’s shift this trend moving forward! Picture a sappy, 80s-reminiscent rom-com, with “Iris” playing at that pivotal, heartwarming moment. Thanks (and you’re welcome) in advance.

Have you been letting it “Linger” lately? I know I have!

I feel like lately everyone has been caught in the lingering embrace of The Cranberries’ smashing hit, “Linger,” from their best-selling album, Everybody Else is Doing It, So Why Can’t We? The track has recently experienced a resurgence in popularity, propelled by recent media attention. But don’t be quick to dismiss it as a mere pop culture fad — this song is a timeless classic, offering a poignant and perhaps necessary, semi-uplifting interlude amidst the sorrowful tones of the rest of the playlist. And there’s nothing more cathartic than belting out the heartfelt lines: “So why were you holding her hand? / Is that they way we stand? / Were you lying all the time? / Was it just a game to you? / But I’m in so deep / You know I’m such a fool for you / You got me wrapped around your finger / Do you have to let it linger?”

“Moon Song” by Phoebe Bridgers has got to be one of the most devastating songs of all time. With its twin “Savior Complex,” I can recall many a moment when I’ve found myself sobbing so intensely that it could rival scenes straight out of a movie. Heartbreak, in all its complexities, is a strange journey. As we usher in the new year, here’s to wishing everyone a relationship that is very “Moon Song”-less.

Now this is a bit more complex, because I’m going to hit you with a line up. I beg you to listen to “Losing My Religion” by R.E.M., followed by “Everything Reminds Me of Her” by Elliot Smith, and topped off with “I’m Not in Love” by 10cc.

This combination is nothing short of lethal, a symphony that reeks of nostalgia and unfolds as a visceral experience. I won’t delve into why it’s so good; it simply is. If you find solace in embracing your emotions, or perhaps consider yourself a bit of a musical masochist, this lineup is tailored just for you. Sit back, immerse yourself, and let the melancholic beauty of these tracks speak for themselves.

No breakup playlist can claim true completeness without the inclusion of Jeff Buckley’s most infamous song, “Lover, You Should’ve Come Over.” This masterpiece is a symphony of sorrow, where the very first note strikes you with a poignant pang of sadness. From the moment he utters the initial word, a tidal wave of emotions crashes over you. Have you ever experienced a relentless onslaught of memories? Well, this song has the power to transport you right there, to the heart of those rememberings. It’s a musical journey through the depths of longing and regret, making it an essential addition to any collection of breakup ballads.

Once more, for those yearning for a cathartic cry to release all thoughts of your ex before the ball drops, these are my heartfelt recommendations. And to those fortunate souls embracing their dearest tightly, congratulations and a happy New Year!

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